Partition Coefficients and Their Uses

Chemical Reviews
Volume 71, Number 6 December 1971
525
PARTITION COEFFICIENTS AND THEIR USES

ALBERT LEO,* CORWIN HANSCH, AND DAVID ELKINS
Department of Chemistry, Pomona College, Claremont, California 91711 Received March 31, 1971
Contents
I. Introduction A. Purpose B. Historical 11. Theoretical A. Henrys Law B. Nonideal Behavior of Solutes C. Thermodynamics of Partitioning Systems D. Energy Requirements for Phase Transfer 111. Experimental Methods IV. Linear Free-Energy Relationships among Systems V. Additive-Constitutive Properties VI. Uses of Partition Measurements A. Countercurrent Distribution B. Measurement of Equilibria C. Relationship to HLB and Emulsion Systems D. Measurement of Dissolution and Partitioning Rate of Drugs E. Liquid Ion-Exchange Media and Ion-Selective Electrodes F. Measurement of Hydrophobic Bonding Ability. Structure-Activity Parameters VII. The Use of Table XVII VIII. Glossary of Terms
525 525 526 527 527 521 531 532 531
538 542 548 548 548
548 549
550
550 551 554
1. Introduction
A. PURPOSE
In spite of the scientific communitys continuing interest over the past 90 years in partitioning measurements, no comprehensive review of the subject has ever been published. In fact, no extensive list of partition coefficients has appeared in the literature. The largest compilation is that of Seidell; smaller compilations have been made by Collander, ~ - von Metzsch,G 5 and Landolt. The task of making a complete listing is nearly
(1) A . Seidell, Solubility of Organic Compounds, Vol. 11, 3rd ed, Van Nostrand, Princeton, N. J., 1941. (2) R.Collander, Physiol. Plant., 7, 420 (1954). (3) R.Collander, Acta Chem. Scand., 3, 717 (1949). (4) R.Collander, ibid., 4, 1085 (1950). (5) R.Collander, ibid., 5 , 774 (1951). (6) F.von Metzsch, Angew. Chem., 65,586(1953). (7) Landolt-Bornstein Zahlenwerte and Functionen, Vol. 2, SpringerVerlag, Berlin, 1964,p698.
impossible since Chemical Abstracts has not indexed the majority of the work of the last few decades under the subject of partitioning. While reference may be made under the name of a compound, this is of very little help in organizing a list of known values. Actually, in recent years relatively few partition coefficients have been determined in studies simply devoted to an understanding of the nature of the partition coefficient. The vast majority have been measured for some secondary reason such as the correlation of relative lipophilic character with biological properties of a set of congeners. In the course of structure-activity studies undertaken by this laboratory over the past decade, many values for partition coefficients of drugs have been found in the biochemical and pharmaceutical literature. From references in these papers, many other values have come to light. As these values have been uncovered, they have been fed into a computer-based keyed-retrieval compilation which, while admittedly not complete, is still far more comprehensive than any yet published. This compilation is not the primary reason for the present review. Work8 on the correlation of hydrophobic bonding in biochemical systems with partition coefficients has been greatly hindered because of the lack of any survey of the field. This review is written in the hope that the organization of the scattered works on this subject will be of help to others. However, the more dynamic part of the subject is the use of the partition coefficient in the study of intermolecular forces of organic compounds. This subject, while still in.the embryonic stage, holds promise for the better understanding of the interaction of small organic molecules with biomacromolecules. Equation 1 is one of many known examples9 of a log 1 = 0.75 log P f 2.30 C
n r S 42 0.960 0.159
(1)
linear free energy relationship relating two partitioning-like processes. In eq 1, C is the molar concentration of organic compound necessary to produce a 1:1 complex with bovine serum albumin via equilibrium dialysis. This partitioning process is related linearly to log P which is the partition COefficient of the compound between octanol and water. The number of molecules studied is represented by n, r is the cor(8) C. Hansch, Accounts Chem. Res., 2,232 (1969). (9) F. Helmer, K.Kiehs, and C. Hansch, Biochemistry, 7 , 2 8 5 8 (1968).
526 Chemical Reviews, 1971,Vol. 71, No. 6
A. Leo, C Hansch, and D Elkins .
relation coefficient, and s is the standard deviation from regression. Many such linear relationships between solutes partitioned in different solvent systems have been uncovered (section IV). A summary of this work should provide a better understanding of the octanol-water model system and further the application of such linear free energy relationships to partitioning-like processes in more complex biological systems. Another aspect of this review is to summarize the present understanding of the recently discoveredlo additive-constitutive character of the partition coefficient. This property promises to be of value in studying the conformation of molecules in solution.
B. HISTORICAL
The distribution of a solute between two phases in which it is soluble has been an important subject for experimentation and study for many years. In one form or another this technique has been used since earliest times to isolate natural products such as the essences of flowers. The first systematic study of distribution between two immiscible liquids which led to a theory with predictive capabilities was carried out by Berthelot and Jungfleisch.l1 These investigators accurately measured the amounts present at equilibrium of both IZ and Brz when distributed between CSZand water. They also measured the amounts of various organic acids, HzS04,HC1, and NH3 when distributed between ethyl ether and water. From these early investigations came the first appreciation of the basic fact that the ratio of the concentrations of solute distributed between two immiscible solvents was a constant and did not depend on the relative volumes of solutions used. It was concluded from these early observations that there was a small variation in partition coefficient with temperature, with the more volatile solvent being favored by a temperature decrease. It was also evident that some systems, notably succinic acid partitioned between ether and water, did not obey their simple rule even in dilute solution, but they intuitively felt the rule would be justified nonetheless. In 1891, Nernst made the next significant contribution to the subject. l 2 He stressed the fact that the partition coefficient would be constant only if a single molecular species were being considered as partitioned between the two phases. Considered in this light, partitioning could be treated by classical thermodynamics as an equilibrium process where the tendency of any single molecular species of solute to leave one solvent and enter another would be a measure of its activity in that solvent and would be related in the usual fashion to the other commonly measured activity functions such as partial pressure, osmotic pressure, and chemical potential. As the primary example of a more exact expression of the Partition Law, it was shown that benzoic acid distributed itself between benzene and water so that
coefficient for the benzoic acid monomer and the dimerization constant for the acid in benzene.la Since benzoic acid exists largely as the dimer in benzene at the concentration employed, the monomer concentration in benzene is proportional to the square root of its total concentration in that solvent. Of coulse, Nernst was also aware that, at low concentrations, the concentration of benzoic acid in the aqueous phase would have to be corrected for ionization. This association and dissociation of solutes in different phases remains the most vexing problem in studying partition coefficients. For a true partition coefficient, one must consider the same species in each phase. A precise definition of this in the strictest sense is impossible. Since water molecules and solvent molecules will form bonds of varying degrees of firmness with different solutes, any system more complex than rare gases in hydrocarbons and water becomes impossible to define sharply at the molecular level. Very little attention has been given to the fact that solutes other than carboxylic acids may carry one or more water molecules bound to them into the nonaqueous phase. This is quite possible in solvents such as sec-butyl alcohol which on a molar basis contains more molecules of water in the butanol phase than butanol! During the early years of the twentieth century a great number of careful partition experiments were reported in the literature, most of which were carried out with the objective of determining the ionization constant in an aqueous medium of moderately ionized acids and bases. As a point of historical fact, the method did not live up to its early promise, partly because of unexpected association in the organic solvents chosen and partly because of solvent changes which will be discussed in detail in a following section. After reliable ionization constants became available through other means, partitioning measurements were used to calculate the association constants of organic acids in the nonaqueous phase as a function of the temperature. This yielded values of A H , AS, and AG for the association reaction.14-18 However, any calculation of self-association constants from partition data alone can be misleading when hydrate formation occurs. 19,20 Asearly as 1909, Herzzlpublished formulas which related the to partition coefficient (P) the number of extractions necessary to remove a given weight of solute from solution. His formula, with symbols changed to conform to present usage, is as follows. If W ml of solution contains x o g of solute, repeatedly extracted with L ml of a solvent, and X I g of solute remains after the first extraction, then ( x o - x t ) / L = concentration of solute in extracting phase and xl/W = concentration remaining in original solution.
(13) Occasionally, K values obtained in this fashion have been reported as partition coefficients. In this report all such values have been corrected to true P values whenever the different terminology was apparent. (14) M. Davies, P. Jones, D. Patnaik, and E. Moelwyn-Hughes, J . Chem. Soc., 1249 (1951). ( 1 5 ) J. Banewicz, C. Reed, and M. Levitch, J . Amer. Chem. SOC.,79, 2693 (1957). (16) M. Davies and D. Griffiths, Z . Phys. Chem. (Frankfurt am Main), 2, 353 (1954). (17) M. DaviesandD. Griffiths,J. Chem.Soc., 132(1955). (18) E. Schrier, M. Pottle, and H . Scheraga, J . Amer. Chem. SOC.,86, 3444 (1964). (19) E. N. Lassetre, Chem. Rev., 20,259 (1937). (20) R. Van Duyne, S.Taylor, S. Christian, and H . Affsprung, J . Phys. Chem., 71,3427 (1967). (21) W. Herz, Der Verteilungssatz, Ferdinand Enke, Stuttgart, 1909, P 5.
-vG/C, = K
(2)
where C, is the concentration of benzoic acid in benzene (chiefly in dimeric form), C, is the concentration of benzoic acid in water, and K is a constant combining the partition
(10) T.Fujita, J. Iwasa, and C. Hansch, J . Amer. Chem. Soc., 86, 5175 (1964). (1 1) Berthelot and Jungfleisch, Ann. Chim. Phys., 4,26 (1872). (12) W. Nernst,Z.Phys. Chem., 8, llO(1891).
Partition Coefficients and Their Uses
Chemical Reviews, 1971, Vol. 71, No. 6 527 The symbols and nomenclature associated with partitioning processes have varied considerably. Before the turn of the century, the term distribution ratio was often used. Gradually, partition coefficient has become more widely used since Chemical Abstracts has indexed under this heading rather than distribution ratio. We shall use partition coefficient when referring to data which have been corrected for ionization, dimerization, etc., so that one is presumably referring to the distribution of a single species between two phases. It is appreciated that there is considerable uncertainty about the nature of hydrate formation, and attempts to correct partition coefficients for the relative degree of specijic association with water molecules or solvent molecules are very few. The expression partition ratio should be reserved to refer to uncorrected distributions of solute between two phases. Various symbols such as K , K D ,K p , D,and P have been used to represent the partition coefficient. We have chosen to use P partly because it has become more widely used in recent years than other symbols and because discussions with P very often involve many other equilibrium constants. P stands out from the variety of K values and is more easily followed in discussions, especially since this symbol is used sparingly in the literature pertaining to physical organic chemistry.
xo p = __x1 W L
x1 = x g
x 1
PW PW+L
If x2 is the amount of solute remaining after the second extraction with an equal volume, L , of extractant, then
X?
XI
P W f L pw
= xo ___
[ P K LIZ
(3)
For the general case where n extractions are made, eq 3 takes the general form
Xn
x] +
PW PW+L
(4)
During the 1940s the mechanical technique of multiple extraction was vastly improved, and countercurrent distribution became an established tool for both the separation and characterization of complex mixtures. 2 2 It is beyond the scope of this review to deal with the great wealth of literature on this subject. The interested reader may consult the reviews for detail~.~*#~~ Partition coefficients can be obtained from countercurrent distribution studies and many such values appear in Table XVII. The equation used for such studies is
I E . Theoretical
A. HENRYS LAW
The most general approach to distribution phenomena is to treat the Partition law as a n extension of Henrys law. For a gas in equilibrium with its solution in some solvent in/p
=
T,,,
(5)
where Tn,p represents the fraction of the total material in the r tube distributed through n tubes.24 For distributions involving more than 20 transfers and when P is near unity, the following simpler relationship applies
=
(7)
(63)
where N = position of peak, n = number of transfers, and P = partition coefficient. During the two decades bracketing the turn of the century, while the partition coefficient was being studied by physical chemists as an end in itself, pharmacologists became quite interested in the partition coefficient through the work of Meyer25 and OvertonZe who showed that the relative narcotic activities of drugs often paralleled their oil/water partition coefficients. However, the correlation of so-called nonspecific narcotic activity with partition coefficients did not lead to any really useful generalizations in understanding the mechanism of drug action in the broad sense. Consequently, the interest of both groups in partition coefficients declined greatly. In fact, even the exciting technique of countercurrent distribution did little to stimulate serious studies of partition coefficientsper se. It is only the recent use of partition coefficients as extrathermodynamic reference parameters for hydrophobic bonding in biochemical and pharmacological systems which generated renewed interest in their measurement.*jQ
(22) L. C. Craig and D. Craig in Technique of Organic Chemistry, Vol. 111, Part I, A . Weissberger, Ed., Interscience, New York, N. Y., 1950, p 171. (23) L. C. Craig, Bull. N . Y . Acad. Med., 39,686 (1963). (24) B. Williamson and L. Craig, J . B i d . Chem., 168,687 (1947). (25) H. Meyer, Arch. Exptl. Parhol. Pharmakol., 42, 110 (1899). (26) E. Overton, Studien uber die Narkose, Fischer, Jena, Germany, 1901.
where m = mass of gas dissolved per unit volume and p = pressure at constant temperature. Since the concentration of molecules in the gaseous phase is proportional to pressure, p can be replaced by C1and the mass/unit volume of gas in solution designated by C2.Equation 7 can then be restated as
C2/Ci = K
(8)
In the most general terms, then, the concentrations of any singular molecular species in two phases which are in equilibrium with one another will bear a constant ratio to each other as long as the activity coefficients remain relatively constant. The catch to the above simple definition is that it assumes no significant solute-solute interactions as well as no strong specific solute-solvent interactions. Many large interesting organic compounds deviate considerably from ideal behavior in water and various solvents so that one is not always even reasonably sure of the exact nature of the molecular species undergoing partitioning.
B. NONJDEAL BEHAVIOR OF SOLUTES

In many instances solute molecules can exist in different forms in the two phases. This problem can be illustrated with the relatively simple and well-studied case of ammonia. NHs(vapor)
aqueous
jt(NH3)r
NH3
NHa+ OH-
In this example, Henrys law is not obeyed, and there is wide variation of m/p (or Cz/Cl)with concentration. Calingaert and
528 Chemical Reviews, 1971, Vol. 71, No. 6

Huggins* considered the ionization equilibrium and found that C2/[Cl(l - a)]G K ; the degree of ionization is represented by a,and K was found to be constant to within 3 over a 300-fold range of concentrations. Moelwyn-HughesZ8 points out that if one allows for both ionization and dimerization assigning a value of K = 3.02 mol/l. for the equilibrium constant for the reaction 2(NH3)$ (NH& then a constant partition ratio is obtained for concentrations up to 1.6 M . The equation allowing for both dimerization and ionization can be cast in several forms and the choice is merely one of convenience in handling the data. In treating their data on the distribution of acids between water and toluene, benzene, or chloroform, Smith and White29 assigned the following symbols in developing a useful set of equations.
CI = concentration of total solute in aqueous phase in mol/l. CI= concentration of total solute in organic phase in mol/l.
A. Leo, C. Hansch, and D. Elkins
CzjNa = P ( l / N )
+ constant
2P21K~ (12)
constant
X
N
at the first concentration level - XI = concentration of un-ionized molecules in water at the second level P = concentration single molecules in organic phase/concentration single molecules in aqueous phase KD = dissociation constant of double into single molecules in organic phase K A = dissociation constant of single molecules into ions in aqueous layer
n
= C1
= concentration of ions in aqueous phase = C - XI = concentration of un-ionized molecules in water 1
(in terms of monomer molarity)
It is evident that a plot of (C2/N2)us. 1 jN will yield a straight line with slope = P . If there are sufficient data points, any aberrant values will be apparent, and the concentration beyond which the linear relationship no longer holds is more obvious. A good deal of the data on acids in the literature had never been treated in this manner. To make these calculations from data which recorded a range of total concentrations in each phase (regardless of whether present as dimer, ion, etc.), we have written a small computer program to calculate l / N and CzjNzfor each concentration value and P for each consecutive set of two concentrations. The program also punches a set of cards with C2jN2and l / N values which can then be used with a regression program to eliminate aberrant values and values beyond the true linear relationship. Whenever possible, the P values in Table XVII have been calculated in this way and 95 % confidence intervals have been placed on them. P values so obtained were used to calculate KDvalues in Table 11. A slightlyalteredformofeq 12hasalso beenwidelyused.14t31 Stated in terms of the above symbols, it is
C 2-- P + - 2P2 _ N N KD
For aqueous equilibrium
and
For equilibrium in the organic phase30 (HA)2 J_ 2HA
It is readily apparent that any set of experimental values of Cl and C2 are apt to have one or more aberrant points, and, furthermore, it is not always apparent how high a concentration must be reached before other solvent effects introduce sizable errors into the relationship which assumes a constancy for the two phases. For this reason it is advisable to recast eq 10 in another form.
K D = 2(PN)2/(C2- P N )
which is equivalent to
KD(CZ- P N )
=
2(PN)Z
Multiplying by ~ / K D and rearranging, we obtain N~

(27) G. Calingaert and F. Huggins. Jr., J . Amer. Chem. Soc., 45, 915 (1923). (28) E. A. Moelwyn-Hughes, Physical Chemistry, 2nd ed, Pergamon Press, New York, N. Y., 1961, p 1085. (29) H . Smith and T. White, J . Phys. Chem., 33,1953 (1929). (30) In eq 10, Smith and White omitted 2 in the numerator.
In this form a plot of N us. l j N yields the value of P from the intercept (the partition coefficient at zero concentration where dimerization can be ignored). The value of the dimer dissociation constant can be obtained from P and the slope. It is obvious that dividing both sides of eq 13 by N yields an equation of the form of eq 12 and thus a given set of data should yield the same values for P and K D by either method of calculation. We prefer to use the Smith and White equations, especially where no data points were measured at low concentrations and where, therefore, there can be a wider 95 % confidence interval in the intercept value as compared to the confidence interval on the slope. In calculating partition coefficients or association constants of acids, one is of course quite dependent on the quality of equilibrium constants available. For example, Moelwynin reviewing data reported by Rothmund and Drucker,33 assumed no dimerization of picric acid in benzene and obtained a value of 0.143 for the ionization constant of picric acid in water. If, on the other hand, we accept the value of 0.222 for the KA of picric acid as determined by conductivity measurements34 and recalculate Rothmund and Druckers data, a P value of 48.77 is found instead of 31.78. The K D value, as calculated by eq 12, is very nearly infinity; Le., there is very little association in the benzene phase. This is a departure from the behavior of unsubstituted phenols in benzene. Endo35 used partitioning data to show that the dissociation constant for the phenol trimer in benzene is approximately 1. Ionization and self-association are not the only fates which can befall the carboxylic acid monomer (or other polar molecules) and complicate the calculation of the true partition COefficient and association constant. 19,2O If the solute forms a
Reference 28, p 1081. Reference 28, p 1082. V. Rothmund and K. Drucker, 2. Phys. Chem., 46,827 (1903). J. Dippy, S. Hughes, and L. Laxton, J . Chem. Soc., 2995 (1956). K. Endo, Bull. Chem. SOC. Jap., 1,25 (1926).
(31) (32) (33) (34) (35)
Chemical Reviews, 1971, Vol. 71, No. 6 529
firmly bonded hydrate, there is another set of equilibria to worry about in the organic phase. In order to best explain variation of P with concentration in the system of benzoic acid distributed between benzene and water, it was proposedz0 that three hydrates are present in the benzene. By a rather complex
H
i
I
R-C
P
0-H---0,
p--H-Q
,H H
R-C
OH---<
curve-fitting technique using solubility data of water in benzene and benzoic acid in benzene, equilibrium constants for the three types of hydrates were estimated. In Table I the associa-
Table I
Hydration and Dimerization of Benzoic Acid in Benzene Temo. c Kn P Van Duyne, et a1.20 Method A Method B Schilow and Lepin36 Smitha? Huq and Lodhi-38 Hendrixson39 Hendrixson39
25 25 23.5 25 25 10 40 589 298 109 2605 244
? ?
method discussed above. Sometimes K,,,,, was found to vary M , and in these with concentration at levels below 5 X cases the constant value at higher concentrations was chosen. The variation at the lower concentrations may be more a function of the analytical techniques employed in measurement rather than a meaningful physical phenomenon, although this is by no means completely clear from the data. One must keep the arguments of Van Duyne, et uI.,~O mind when considerin ing these constants. If hydrate formation is always involved with carboxylic acids in solvents such as benzene, then the association constants of Table I1 will generally be too low. Not much in the way of useful generalizations can be made from the data in Table 11. It is of interest that there is a general trend of the degree of dimerization by solvents: toluene > benzene > chloroform > ether. The fact that benzene values > are lower than toluene is likely due to the greater solubility of water in benzene. In fact, the solubility of water in the organic solvent as seen from Table VI11 is in inverse order to the degree of dimerization, water being most soluble in ether and least soluble in toluene. Considering a single solvent, toluene, the dimerization constant appears to increase with the size of the alkyl group, at least up through valeric acid. This effect seems to correlate most closely with Tafts steric parameter, E.. While eq 14 is log Pa,,,, -0.470(=t0.32)Es =
+ 1.989(*0.20)
(14)
0.95 1.31 2.30 1.63 1.56 1.43 2.10
n r S 8 0.824 0.223
quite significant statistically (F1.e = 1 . ) the correlation is 26, not very high. It does suggest, however, that the steric effect of the alkyl moiety of the acid is most important. Adding a term in pK, to eq 14 does not improve the correlation. One cannot place a great deal of confidence in eq 14 since there is considerable overlap between the two parameters, pK, and Ea,for the set of acids under consideration (rz = 0.834).Equation 14 does suggest that the large alkyl groups might inhibit hydrate formation and in this way favor dimerization. There is little trend to be seen in the scattered group of halo fatty acids and substituted benzoic acids, but the statement 40 that the more highly chlorinated acids are more highly associated does not seem supported. In the development of eq 12 and 13 it was assumed that association in the organic phase proceeded no further than the dimer stage. For the case of acetic acid in the benzene-water system, it has been shownlBthat neither partition coefficient nor the dimerization constant values calculated from this type of expression would be markedly altered if some trimer or tetramer were also formed. These authors calculated Kl--3 to be 2.35 X but suggest that this might well be viewed as a correction in the dimerization equilibrium constant and therefore not have any real molecular significance. While there is little or no evidence for association beyond the dimer state for low molecular weight carboxylic acids, other types of solutes have a greater associative tendency. For instance, a sudden increase in P*60 (apparent partition coeffi(41) N. A. Kolossowsky and I. Megenine, Bull. SOC.Chim. Fr., 51, 1000 (1932). (42) W. Herz and H . Fischer, Chem. Ber., 38, 1138 (1905). (43) N. A. Kolossowsky and S. F. Kulikov, 2.Phys. Chem., A169,459 ( 1934). (44) F. S.Brown and C. R. Bury, J . Chem. SOC., 123,2430 (1923).
An average of six different determinations.
tion constants and partition coefficients for benzoic acid in benzene are given, and the results assuming hydrate formation are compared with results neglecting it. It is evident from Table I that the calculations which take hydrate formation into account affect the partition coefficient as well as the dimerization constant. However, if method Bzois accepted, it does not yield values far out of line from those determined by other investigators. Although preferred by Van Duyne, et a f . ,method A is open to criticism for it assumes that the dimerization constant (KZO their paper) is the same in dry benzene as in wet. in Completely apart from any tendency to encourage hydrate formation, the addition of water to benzene could be expected to increase the dielectric constant and by this means alone should lower KD (association).19v40 However, it must be admitted that there is evidence which supports a lesser or negligible role for a change from a dry to a wet organic solvent. l 4 In Table I1 are listed a number of association constants for carboxylic acids in various solvents calculated according to the
(36) (37) (38) (39) (40)
N. Schilow and L. Lepin, Z . Phys. Chem., 101,353 (1922). H . W. Smith, J . Phys. Chem., 26,256 (1922). A. K . M. S.H u q and S.A. K . Lodhi, ibid., 70, 1354 (1966). W. S.Hendrixson, 2.Anorg. Chem., 13,73 (1897). C. Brown and A . Mathieson, J. Phys. Chem., 58, 1057 (1954).
-TolueneAcid
1. Formic
Kassoc
Ref
Table I1 Association Constants of Acids -Benzene-CHClsKasmo Ref Kawoc
Ref
Kamoc
Other sobent
Ref
29 42 133 182 300 200 225 94 450 132" 4.5

0 60
41 42 29 29 29 29 29 29 29 43 42 29 29 29 29 29 29 29 43 43 36 42 29 29 29 29 29 29 29 29 29 29 29 29 29 29
1210 28 94 97 182 140 138 96 68 271 2.2

0
2. Acetic 3. Propionic 4. Butyric 5. Isobutyric 6. Valeric 7. Isovaleric 8. Hexanoic 9. Isohexanoic

10. Crotonic
45 45 42 29 29 29 29 29 29 29 29 42 29 29 29 29 29 29 29
26
60
45 45 29 29 29 29 29 29 29 29 43 46 29 29 29 29 29 29
0.6 43
0
Nitrobenzene cc1, Ether Xylene Ether Xylene
48 45 46 46 49 46
31 52 64 49 80 30 50 136 96O 53 16 35 9.5 25 64 22

0
78
0.5
2"
160
0.1 11. Chloroacetic 12. 13. 14. 15. 16. 17. 18. 19. Bromoacetic Iodoacetic @-Chloropropionic a-Bromopropionic @-Bromopropionic P-Iodopropionic a-Bromobutyric Dichloroacetic 419 1.6
Xylene Ether Xylene Nitrobenzene
46 49 46 43
37
55
100 30 65 133 47 44
0 0
16 61 95 22
157 43 47 29 17 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29 29
0 1440
0 0 0
20. Trichloroacetic
CCla Ether Ether Nitrobenzene Ether Xylene
43 43 46 43 46 46
21. Picric 22. Benzoic 23. o-Toluic 24. p-Toluic 25. o-Methoxybenzoic 26. p-Methoxybenzoic 27. o-Chlorobenzoic 28. m-Chlorobenzoic 29. pChlorobenzoic 30. o-Nitrobenzoic 31. m-Nitrobenzoic 32. pNitrobenzoic 33. o-Bromobenzoic 34. m-Bromobenzoic 35. Salicylic 36. Acetylsalicylic 37. Methylanthranilic 38. Phenylacetic 39. Anthranilic
a
0.6 295 298 108
33 37 20 36
79 21 291 3.9 82 106 25

0 0
33 120 1 3.3
0
0.3 11
0 0
312
Xylene
46
78
0
1 61
0
133
XyIene
46
30
0
17 143 145
151
29
44 75 85 56 770
57
Xylene
46
Doubtful value.
cient or partition ratio) of dibutyl phosphate in hexane (when Cor,= 0.05 M) can be explained in terms of the conversion of the dimer to a polymer chain.
O-----H--O,
( RO ' P L )
For solutes showing negligible ionization (the work with the phosphate esters was done in 0.1 M HN03) in the aqueous phase, it is easy to test if a higher polymer is formed in the organic phase. It has been pointed outas that if a trimer is formed
(45) A. Bekturov,J. Gen. Chem., 9,419 (1939). (46) H. W. Smith,J.Phys. Chem., 25,204,605 (1921). (47) W. Herz and M. Lewy, Z . Elektrochem., 46,818 (1905). (48) N. A. Kolossowsky and A. Bekturov, Bull. SOC. Chim. Fr., 2, 460 (1935). (49) W. U.Behrens, Z . Anal. Chem., 69,97 (1926). (50) D. Dyrssen and L. D. Hay, Acta Chem. Stand., 14, 1091 (1960).
\o++-o/
P(OR),
a
OR OR
I I --I)=P-OH-~-O=P-OIII I OR
OR
Kassoc
Ctr/(CJ3
(15 )
where C,, = concentration trimer in organic phase and C,,, = concentration monomer in organic phase. Hence
C,,,
=
Cmo,
+ 3Ctr = Cmo, + 3KassocCmm3
(16)
where Cap, = total concentration solute in organic phase (regardless of form), and C,, = concentration in water phase (no polymerization). Assuming trimer cannot exist in the aqueous phase, the true partition coefficient for monomer is
P
=
CmonjCv
Therefore
C P - PCw SP P*
=
+ 3Kassoc(PCw)3
(17)
acid in the benzene-water system, it was concluded16that the dimer association constant in water is only one-fifth this large (i.e., 0.033). Nevertheless, the effect becomes quite large with dodecanoic acid, making the determination of a true monomer partition coefficient almost impossible.s6Thus the present data have not completely eliminated the possibility of head-to-head dimerization of fatty acids in the aqueous phase, but the preponderance of new evidence l a favors the chain entwinement viewpoint. Distribution studies have also been made with other types of solutes which are known to form micelles at relatively low concentrations in water such as alkylpyridinium and pyridonium chlorides and p-tert-octylphenoxypolyoxyethanolsurfactants. Over a range of solute concentrations below cmc, constant P values have been observed. 5 7 , 5 8
P f 3K,,,,,P3CW2
A plot of the apparent partition coefficient, P*, us. the water concentration squared, C,v2,should give a straight line with the intercept yielding the value P and the slope yielding the value K,,,,,. Many investigators have followed similar derivations, but some have not limited the applications to relatively un-ionized solutes. For example, AlmquisV1 observed a straight line plot of CJC, us. C, with picric acid in the chloroform-water system. Assuming the applicability of the general relationship
C,/C,
=
C. THERMODYNAMICS OF PARTITIONING SYSTEMS

Solvent systems which are almost completely immiscible (e.g., alkanes-water) are fairly well behaved and lend themselves to more rigorous thermodynamic treatment of partitioning data than solvent systems which are partially soluble in each other. 17,59,6O The following development can be applied more strictly to the former systems, but the departures from ideality exhibited by the more polar solvent systems are not so great as to render this approach valueless. They will be discussed later. It should be noted here that the thermodynamic partition coefficient is a ratio of mole fractions (I = X J X , ) , and it should not be confused with the more common expression of P which is a dimensionless ratio of concentrations. CratinS1 has presented a lucid discussion of some of the aspects of the thermodynamics of the partitioning process. The following discussion is drawn from his analysis which relies heavily on extrathermodynamic assumptions. For each of the i components comprising an ideal solution, the following equation is assumed to hold
p , ( T , P , X ) = ple(T,P)3- RT In X , (19)
n(KassooPnCn-l) P
(18)
he calculated that the true partition coefficient was 0.46 and the association constant was 8.6. However, if we use the measured ionization constant for picric acid, we get constant values of P = 15.8 and K,.,,, = 0. As pointed out above, picric acid is apparently not associated in benzene, and we would expect it to be even less associated in chloroform. Furthermore, the value of 15 for P fits in much better when compared to the octanol-water system by means of the regression equation A in Table VIII. Most investigators have assumed that the amount of dimerization of aliphatic acids in the aqueous phase is insignificant, an assumption which seems reasonable if only a head-tohead dimer is possible.
0---HO, R--C / ,CR OH-- -o/
However, with higher homologs other possibilities exist. Micelle formation becomes quite significant even at low concentrations with long-chain fatty Even though one works at concentrations below the critical micelle concentration (cmc), the problem of association in the aqueous phase cannot be eliminated. Entwinement of the long alkyl chains occurs in very dilute ~ o l u t i o n sCareful examination of cryo.~~ scopic data, Raman spectra, and vapor pressure measurem e n t ~ ~ ~ , ~ been interpreted to yield aqueous phase dihave ~ , ~ 5 merization constants for carboxylic acids which increase with chain length: formic, 0.04; acetic, 0.16; propionic, 0.23; butyric, 0.36. From a careful study of the distribution of acetic
(51) H . Almquist, J . Phys. Chem., 37,991 (1933). ( 5 2 ) J. L. Kavanau, Structure and Function in Biological Membranes, Vol. I, Holden-Day, San Francisco, Calif., 1965, p 11. (53) P. Mukerjee, I<. J. Mysels, and C. I. Dulin, J . Phys. Chem., 62,
where pee,' is the chemical potential of pure i in the solution under specified conditions, and X , is its mole fraction. p, is not the actual chemical potential of pure i but the value it would have if the solution remained ideal up to X , = 1 . It can be shown6 that, for dilute solutions, the chemical potential based on mole fractions is larger than that based on molar concentrations by a factor of RT In where V, is the molar volume of solvent and therefore
reo,
p , ( T , P , X ) = ple(T,P)
+ RT In Vs+ RT In C ,
(20)
An interesting approach to the study of the intermolecular forces involved in partitioning is to assume that the free energy of transfer of a molecule can be factored into the contributions of its various parts; that is, P is an additive-constitutive property of a molecule (see section V). CratinG1 considered the thermodynamic implications of this concept. Assuming that the total transfer free energy of a molecule ( p t ) is made up of a
(56) C. Church and C. Hansch, unpublished results. (57) E. Crook, D. Fordyce, and G . Trebbi, J . Colloid Sci., 20, 191 (1965). (58) H. L. Greenwald, E. I<. Kice, M. Kenly, and J. Kelly, Anal. Chem., 33,465 (1961). (59) R. Aveyard and R. Mitchell, Trans. Faraday SOC., 65,2645 (1969). (60) R. Aveyard and R. Mitchell, ibid., 66,37 (1970). (61) P. D. Cratin, 2nd. Eng. Chem., 60, 14 (1968).
1390 (1958). (54) A. Katchalsky, H . Eisenberg, and S. Lifson, J . Amer. Chem. Soc., 73, 5889 (1951). ( 5 5 ) D. Cartwright and C. Monk, J . Chem. SOC., 2500 (1955).
532 Chemical Reviews, 1971, Vol. 71, No. 6 lipophilic component &L) and n hydrophilic groups ha), we may write pt(w> = pL(w) pt(O) Assuming ideal behavior pt(w)
= pL'(w) = pL(0)
A. Leo, C. Hansch, and
D. Elkins
+ npH(w) + npH(O)
40) ~ L ' ( o ) =
+ ~PH'(w) + RT In X(W) + WH'(O) + RT In X(O)
enthalpy of transfer by measuring P' over a range of temperatures. In practice this is rather imprecise because of two implied assumptions: first, that the levels of each solvent dissolved in the other remain constant over the temperature range; second, if P is measured in terms of concentrations, that the ratio of solvent molar volumes remains constant also. For this reason the preferred method of obtaining the enthalpy of transfer is by measuring the heats of solution in two separate solvents, whence
Converting from mole fractions to concentration terms, the above equations become pt(w) do)
= =
ADo = ARt,"
AGt,"
A H " ( w ) - AH"(0)
(26)
The entropy of transfer can, of course, be calculated from

=
~L'(w) WH'(W)
+ + R T In V"(w) + RT In C(w) pL'(o) + npI?(o) + R T In Vo(o)+ RT In C(O) + RT In [V"(w)/V"((o)] +

n[p~'(w) - p~'(0)l = +RT In P (21)
A~L' 2.3RT
AHt,"
- TASt,"
(27)
At equilibrium pt(w) = pdo); hence equating equations, collecting terms, and replacing C(o)/C(w) by P, we obtain [pLB(w)- p~'(o>l Setting Ape
=
p'(w) - p'(o), eq 21 takes the form
nAw' logP=--+2.3RT
+ log [~"(W)/V0(O>l (22)

+
If eq 22 holds, a plot of log P us. n will be linear with a slope equal to Apne/2.3RT and an intercept of Ap~'l2.3RT log [Vo(w)/Vo(o)]. Cratin illustrated the validity of eq 22 by plotting the data of Crook, Fordyce, and Trebbi57for tert-octylphenoxyethoxyethanols of the type
~O-(C~I-CH.O~,~CH.CI~.OH
octyl
partitioned between isooctane and water. Compounds with n varying from 1 to 10 were studied. A good linear relation was obtained from n = 3 to n = 10. A slight departure from linearity for n = 1 and 2 was found. The linear relationship between n and P i s given as 58 log P
=
-0.442n
+ 3.836
(23)
From eq 23 the standard free energy change (25') for the transfer of a mole of -CH~CHZO-from isooctane to water is -0.602 kcal and the free energy change (0 w) for the p-tert-octylphenoxyethoxy group is 6.52 kcal/mol. Of course since the partitioning data on the phenoxyethoxyethanols were obtained at a single constant temperature, this is not a very rigorous test of eq 22 since under this condition, V'(o)/V'(w) will also be constant. Nevertheless, eq 22 does define the necessary conditions for additivity of log P values. The standard free energy of transfer of solute in the partitioning process is given by
-) .
Aveyard and M i t ~ h e lhave ~ ~ ~ ~ these calculations l ~ performed for aliphatic acids and alcohols partitioned between alkanes and water. They find much greater enthalpies for the alcohols which they ascribe to the "dehydration" of the O H function during transfer. Although the acids are also "dehydrated," they are thought to recover much of this energy in the hydrogen bonding of dimerization. The corresponding AS values for the acids are much smaller than for the alcohols, and thus the net free energy changes are not greatly different. The changes in miscibility of more polar solvent systems as a function of solute concentration have been studied in only a few ~ y s t e m s . ~ ~ - ~ ~ experience has shown that the However, partition coefficient at low solute concentrations is usually not highly dependent on this effect. Even with solvent pairs as miscible as isobutyl alcohol-water, the effect is small with solutes a t 0.01 M or less, and solvent pairs less miscible than chloroform-water will easily tolerate 0.1 M solute without appreciable miscibility changes. Equation 25 shows how one would expect the partition coefficient to vary with temperature. However, it is not very enlightening from a practical point of view, for the necessary heats of solution are rarely available and, furthermore, there is the added unknown of the dependence of solvent molar volume on temperature. The effect of temperature on P is not great if the solvents are not very miscible with each other. A summary in Table I11 of results of varying degrees of accuracy for a variety of solutes in different solvent systems indicates the effect is usually of the order of 0.01 log unit/deg and may be either positive or negative. Insufficient data are present to attempt any useful generalizations.
D. ENERGY REQUIREMENTS FOR PHASE TRANSFER

The relative roles of the various binding forces which determine the way a solute distributes itself between two phases
(62) G. Forbes a n d x . Coolidge,J. Amer. Chem. Soc., 41, 150 (1919). (63) P. Grieger and C. Kraus, ibid., 71, 1455 (1949). (64) E. Klobbie, 2.PhJ>S. Chem., 24,615 (1897). (65) D. Soderberg and C. Hansch, unpublished analysis. (66) A. Hantzsch and F . Sebalt, 2.Phys. Chem., 30, 258 (1899). (67) R. L. M. Synge, Biochem.J., 33, 1913 (1939). (68) T. S. Moore a n d T . F . Winmill, J. Chem. Soc., 101,1635 (1912). (69) E. M. Renkin, Amer. J. Physiol., 168, 538 (1952). (70) H . Meyer, Arch. Exp. Pathol. Pharmakol., 46,338 (1901). (71) J. Mindowicz and I . Uruska, Chem. Abstr., 60,4854 (1964). (72) R. C. Farmer and F. J. Warth, J. Chem. SOC., 1713 (1904). 85, (73) T. Kato, Tokai Denkyoku Giho, 23, 1 (1963); Chem. Abstr., 60, 8701 (1964). (74) J. Mindowicz and S. Biallozor, ibid., 60,3543 (1964).
Act?
Ape
R T In P'
(24)
With the usual assumption that the standard molar enthalpy change is not temperature dependent in the range studied,el it is true that
b In ~- P'
T
A - -R B RT2
where An' is equivalent to the standard enthalpy of transfer between the two solvents. It is thus possible to calculate this
Chemical Reviews, 1971, Vol. 71, No. 6 533 Table III Temperature Effect on Log P
Solvent-water Octanol
Solutea
Ethyl ether Chloroform
Hexanoic acid Octanoic acid n-Butylpyridinium bromide n-Tetradecylpyridinium bromide Acetic acid Succinic acid Acet yl-d-leucine Acet yl-d-leucine Methylamine Ammonia Antipyrine Antipyrine Ethanol o-Phenylenediamine p-Phenylenediamine p-Nitrosomethylaniline Acetic acid
2-Methyl-5-ethylpyridine 2-Methyl-5-ethylpyridine 2-Methyl-5-ethylpyridine
Temp, "C 4-22 4-22 4-22 4-22

0-25
A log PJdeg
1.7 x 10-3 -1.0 x -1.0 x -1.2 x -0.9 X -0.9 X -1.3 x 1.0 x 0.8 X 1.2 x 1.5 x 1.1 x 3.4 x 4.4 x 2.1 x
0.0
10-2
10-2
15-25 4-27 24-37 18-32 18-32 7-36.5 7-36.5 3-30 20-70 20-70 6-25 6-18.5 10-30 30-50 10-30 30-50 18-32 18-32 18-32 20-60 20-60 15-35 25-60 Average
=
10-3 10-2 10-2 10-2 10-2 10-2
Ref 56 56 65 65 66 62 67 67 68 68 69 69 70 71 71 72 66 73
73
Oil Olive Cod-liver Cottonseed Benzene
Xylene Toluene
1-Hexanol Heptane Isooctane
2-Methyl-Sethylpyridine Ethylamine Diethylamine Triethylamine Malonic acid Succinic acid p-Chloroaniline p-tert-Octylphenoxynonaethoxyethanol (OPE-9)
10-2 10-2 10-2 10-3 10-3 10-3 3.0 x 10-3 4.5 x 10-3 7.0 x 10-3 7.5 x 10-3 -4.0 x 10-3 1.7 X 1.9 X 1 . 9 x 10-2 -1.2 x 10-3 - 0 . 5 x 10-3 5.5 x 10-3 2.8 X 10-2 9.0 X 10-3
73 73 68 68 68 74 74 75 58
= No correction made for ApKJdT for any of the acids.
has been examined by a number of authors.76Kauzmann7' has given a particularly clear summary of this thinking, especially from the point of view of the interaction of small molecules with proteins, and the following discussion relies heavily on his summary. The study of the hydrocarbons in water shows that although the AH of solution is negative (indicating a favorable enthalpy change by the evolution of heat), such compounds are notoriously insoluble in water. This reluctance to mix with water is a result of a large A S for the process. It is this large energy of reordering the hydrocarbon solute and the water solvent molecules which keeps them in separate phases when placed together. The same phenomenon regulates the distribution of apolar solute molecules in an apolar solvent-water system. Table IV7?illustrates this point. A variety of work, less well defined than that of Table IV, supports the conclusion that the entropic component of AG plays a large role in the position of equilibrium (partition coefficient) taken by nonpolar compounds in nonpolar water-solvent systems. Kauzmann has put forward the following facts. 1. Mixtures of lower aliphatic alcohols with water show positive deviations from Raoult's law, indicating an increase
(75) A . Aboul-Seoud and A . El-Hady, Rec. Trau. Chim. Pays-Bas, 81, 958 (1962). (76) H. Frank and M. Evans, J . Chem. Phys., 13,507 (1945). (77) W.Kauzmann, Aduan. Protein Chem., 14,37 (1959).
Table I V Thermodynamic Changes in Hydrocarbon Transfer T ASUa AH AG," CH4in benzene + CHI in HzO 298 -18 -2800 +2600 298 -19 -2400 +3300 CHI in ether + CH4 in HzO 298 -18 -2500 +2900 CHI in CC14-+ CH4in H20 5050 Liquid propane C3Hsin HzO 298 -23 -1800 298 -23 -1000 +5850 Liquid butane C4Hxoin HzO 291 -14 0 +4070 B Liquid benzene -P C ~ Hin H20 291 -16 0 +4650 Liquid toluene + C7Hs in H20 291 -19 0 f5500 in Liquid ethybenzene -r C ~ H N HzO S, and G , refer to the unitary entropy and free energy in cal/mol.
+
in unitary free energy (AG, > 0) for the transfer of alcohol from alcohol to water phase, this despite the fact that heat is evolved (AH < 0) on the addition of these alcohols to water. Therefore AS, = (AH, - AG,)/T < 0 when an alcohol molecule is transferred to water. 2. The solubilities of many liquid aliphatic compounds (e.g., 3-pentanone, butanol, ethyl acetate, ethyl bromide) in water decrease with increase in temperature. Hence AHfor the transfer process must, according to the principle of Le Chatelier, be <O. The fact that some of these substances are extremely soluble in water means that AGu > 0. Therefore, AS, for the mixing must be negative. Similar to this is the
fact that on heating aqueous solutions of such compounds as nicotine, sec-butyl alcohol, etc., separation into two phases results at temperatures not far above room temperature. 3. The formation of micelles from detergent molecules in water is accompanied by very small heat changes; that is to say, the dissociation of micelles into individual molecules does not depend on a large positive value of AH. Hence it is assumed that this association-dissociation reaction is controlled largely by a large negative AS. The origin of the large negative unitary entropy change and the small negative enthalpy change involved in partitioning between aqueous and nonaqueous phases was first clearly appreciated by Frank and Evans. They reached the conclusion that when organic compounds are placed in water, the water molecules arrange themselves around the apolar parts in what was termed iceberg structures. The word iceberg was, perhaps, not too well chosen for it was not meant to imply that the structure was as rigid or as extensive as in pure ice, and it differed further in being denser rather than lighter than water. This is apparent from the data in Table V.77
Table V Volume Changes in Transfering Hydrocarbons from Nonpolar Solvents to Water
AV, mllmol
_ _ _ _ ~
The partition coefficient per -CHz- in an alkyl chain can then be defined as
where a and p refer to the organic and aqueous phases, respectively. This is assuming that the motions of internal rotation are separable from all other motions and that the internal rotation contribution has been assumed representable as the product of n equivalent factors. At room temperature, if kT is much smaller than the spacing between ( e o ) and (e1) or between E O and el, then P E ( $ ~ / ~ g ) 3 n ( e - ( o ) - f ) /* k T 0 If $,/ICp varies little with n and (BO) eo
P,/P,-l E 3 or log P(cH~) 0.5 E

Aranow and Witten present partition data to show that the difference in P values between adjacent members in a homologous set of fatty acids is about 3. This factor has also been observed by others4~Q~80 a variety of homologous for series. A -CF2- group would be expected to affect its environment a great deal more than a -CHr unit would,7Qbut it still has a very similar geometry. Therefore, it was predicted that the P values of a hydrocarbon chain should differ from a fluorocarbon chain if the flickering cluster theory holds, but should be nearly the same if Aranow and Wittens theory holds. The following set (Table VI) of partition coefficients
CHa in hexane -+ CHI in HzO CZH6 in hexane + C2H6 in HzO Liquid propane + C3H8 in H1O . Liquid benzene +. CEHE H20 in
-22.7 -18.1 -21 .o -6.2
Table VI
Octanol-Water Partition Coefficients of FIuoro Compounds These structures were later referred to as flickering clusters to indicate their lack of stability. Since the entropy lost in freezing a mole of water is 5.3 cal/deg and the unitary entropy loss per mole of hydrocarbon entering the aqueous phase is only 20 cal/deg (see Table IV), either only four or five molecules are associated with each hydrocarbon unit or the structure is less firm than in pure ice. The Frank-Evans point of view is that the stripping of the form-fitting sweateF of water molecules from the apolar part of the solute results in a large entropy change in the randomization of the water molecules. An alternative point of view is that of Aranow and Witten.7QThey reason that in the aqueous phase the apolar chain of a solute molecule is rigidly held in a favored rotational configuration by the structured layer of water molecules surrounding it. In the organic solvent its rotational oscillations are relatively unrestricted. They write the canonical single particle partition function, 2, for a molecule having n carbon-to-carbon bonds in the apolar environment as
Log P
1. 2. 3. 4.
A log PICFz
0.82 0.58 0.94
CF3CHzOH CFaCFZCHZOH CF~CFZCF~CH~OH CFaCOOCaHs 5. CF$2FzCOOCzHb
0 . 4 1 =t 0.03 1.23 f 0.06 1.81 f 0.06 1.18 f 0.04 2.12 i 0 . 0 4
0 Log P values are the result of four separate determinations made at room temperature using vapor-phase chromatography for analysis. Unpublished data: C. Church, F. Helmer, and C. Hansch.
Because of the threefold increase in the number of energy levels, the corresponding partition function in the water phase is
throws some light on the problem. In comparing compounds 1 and 2, for example, one must keep in mind the fact that the electron-withdrawing groups, when placed near elements containing lone pair electrons, usually raise the partition coefficient by an increment greater than simple additivity. However, uI for CF3 is 0.41 and uI for C2Fsis 0.41B1 that this effect is ruled out. Two of so the three values are considerably higher than the value of 0.5/CFz predicted by the Aranow-Witten hypothesis, and therefore the partitioning data favor the Frank-Evans hypothesis. Hydrogen bonding is the next factor to consider in studying the energy requirements for phase transfer. This factor is of paramount importance in determining the character of both the solute and the organic solvent phase. Compounds such as
(80) C. Hansch and S. M. Anderson,J. Org. Chem., 32,2583 (1967). 87,2410 (1965). (81) W. A . Sheppard, J . Amer. Chem. SOC.,
(78) E. Grunwald, R . L. Lipnick, and E. I<. Ralph, J . Amer. Chem. Soc., 91,4333 (1969). (79) R . H. Aranow and L. Witten,J.Phys. Chem., 64, 1643 (1960).
alcohols, esters, and ketones have quite different properties than hydrocarbons. Moreover, as solvents, it is not simply the hydrogen bonding character of the pure compound which must be considered. One must keep in mind that rather large amounts of water (especially when figured in molar terms) are present in these oxygen-containing solvents when saturated during the partititoning process (see Table VIII). For example, octanol dissolves in water only to the extent of 0.0045 M . However, the molar concentration of water in octanol is 2.30. The transfer of an alcohol or acid from the water phase to a hydrocarbon phase may involve complete dehydration of the polar OH or COOH function, It seems highly unlikely that such complete dehydration would occur in, say, butanol which is 9 M with respect to water content at saturation. Even in octanol, which is 2.3 M with respect to water at saturation, it is likely that most highly polar functions would be more or less solvated by water and/ or the hydroxyl function of the alcohol. Certain solvents such as alcohols and amines can act as both donors and acceptors in hydrogen bonding. This increases their versatility as solvents. For this reason Meyer and Hemmis2 suggested using oleyl alcohol-water partition coefficients as a reference system for evaluating partitioning of drugs in biological systems. Earlier workers had used esters (olive oil, cotton seed oil, etc.) to represent lipophilic biophases. Since many NH and OH groups are present in enzymes and membranes, it is not surprising that alcoholwater systems give better correlations and thus have become more widely used as extrathermodynamic reference systems. Other intermolecular forces which must be considered in the partitioning process are dispersion forces arising out of electron correlation. It seems that these would play a minor role in setting equilibrium positions of solutes. Dispersion forces involved in complex formation in solution will largely cancel out since, when a solute molecule leaves one phase and enters a new phase, it exchanges one set of London interactions for an0ther.8~ The energy required to transfer from the aqueous phase to the organic phase any solute which contains two or more formal charges is obviously going to depend heavily on the dielectric constant of the particular organic phase in question. Most of the water-immiscible organic solvents have dielectric constants much lower than that of water, and thus charged solutes must contain rather large hydrocarbon residues to have positive log P values. This combination makes them very surface active and usually results in difficulties of measurement. Amphoteric molecules such as amino acids, tetracycline, or the sulfa drugs are most lipophilic when they contain an equal number of positive and negative charges. Typical dependence of log P upon pH is shown in Figure l. For bases which can accept one or more hydrogen ions, An the partition coefficient, PA^ +,is related to the partition coefficient of an associated strong acid, Pa-, by the expression
(31) This relationship for the 2-butanol-water system has been verifieds4 by measuring PA%- of ammonia, alanine, L(82) K.H. Meyer and H . Hemmi, Biochem. Z., 277,39 (1935). (83) R. S . Mulliken and W. B. Person, J . Amer. Chem. Soc., 91, 3409 (1969). (84) F.Carpenter, W.McGregor, and J. Close, ibid., 81,849(1959).
+
I00
I D
08 1 0
05
P
I
P*
04
02
01
4
PH
1 0 0
4
PH
12
Figure 1. Variation of apparent partition coefficient with pH: (left) J. Colaizzi and P. Klink, J. Pharm. Sci.,58, 1184 (1969); (right) W. Scholtan, Arzneim-Forsch., 18, 505 (1968).
PA,,
k[Pa+I
arginine, and L-histidyl-L-histidine, as well as P=t of the strong acids HOEtS03H, CH3S03H,HC1, HBr, HN08, and HC104. A log-log plot of the P values gave a series of straight lines with a slope of 1 for ammonia and alanine, 2 for Larginine, and 3 for L-histidyl-L-histidine. Solutes which are ionized and completely dissociated in the aqueous phase present additional complications to the treatment of partitioning as strictly an equilbrium process, such as given in section 11. The identity of the solute species in both phases is rarely assured. If electrical conductivity resulted solely from the current-carrying capability of single ions, then salts in organic solvents with relatively high dielectric constants (e.g., nitrobenzene, 36.1 ; or nitromethane, 39.4) could be considered to be over 90% dissociated into single ions at M.85*86 But as the dielectric constant decreases, the mutual energy of configurations where there are three ions in contact (A-CS-A-) becomes comparable to kT.87 At this point they are thermally stable and capable of carrying current, and therefore conductance is not proof per se of complete dissociation. Even relatively hydrophilic ion pairs can be accommodated in a lipophilic solvent such as cyclohexane if this solvent contains a small amount of a dipolar solvating agent. In the instance where the cation is the large lipophilic member of the pair, the most effective solvating agents appear to be those with acidic protons, e.g., chloroform, alcohols, and phenols.88 In the reverse situation where the small cationic charge is unshielded, solvating species with nucleophilic sites (e.g., ethers, ketones, amides, and phosphate esters) are most effective. In considering the partitioning of carboxylic acids and amines, it is convenient to work with the A log P resulting from the addition or removal of a proton to create an ion. (This is analogous to the definition of x values taken up on p 542.) By this convention, A log P = (log P,,,) - (log Pneutral) will always have a negative sign for the more and polar ion is obviously more hydrophilic. For aliphatic acids, A log P is about -4.06; for salicylic, it is -3.09; for p-phenylbenzoic, it is -4.04. For a simple aliphatic amine (dodecyl), the A log P of protonation is - 3.28.
(85) H. Falkenhagen, Electrolyte, S. Herzel, Leipzig, 1932. (86) J. C. Philip and H . B. Oakley, J . Chem. Soc., 125,1189 (1924). (87) R. Fuoss and F. Accascina, Electrolytic Conductance, Interscience, New York, N. Y., 1959,p 222. (88) T. Higuchi, A. Michaelis, T. Tan, and A. Hurwitz, Anal. Chem., 39, 974 (1967).
,+
For amines containing an aromatic ring, the A log PH+ values tend to vary (see Table XVII): phenothiazines = - 3.65 Ce.Hs(CH2)sNHt = -2.92 procaine = -4.14 Protonating an aromatic nitrogen appears intermediate ; e.g., for acridine, A log PH+ = -3.90. Very little difference in the octanol-water log P was observed for the amine salts whether the anion was chloride, bromide, or iodide. It should be noted that if one wishes to measure the log Poctanol a dissociable organic ion, he must buffer the of system more than 4 pH units away from the pK, in most cases, The actual ratio of ionic to neutral form in the organic phase can be determined from the following expressions :
(Oleate) (b)
c1-
(c)
Figure 2. Ion-selective electrode (oleate in nitrobenzene): (a) Counterions which differ in log P; (b) the site ion (for an anion-selective electrode, dodecyl amine might be chosen);
(c) co-ion.
tion coefficient of the ions in that s01vent.g~For instance, the partition coefficient of monovalent cations between any alcohol and water are not greatly different,gl and therefore these solvents are not useful in liquid membrane electrodes. The partition coefficients in nitrobenzene, however, are markedly different,92 this solvent has been employed in a and useful electrode to measure [Li+] in the presence of [Rb+lgO The partition coefficients for the iodides fall in the following order: Li+ < Na+ < K+ < Rb+ < Et4N+ < Bu4N+, which For example, in partitioning an aliphatic carboxylic is the order also found for the solvent system diisopropyl acid with a pK, of 4.5 and the aqueous phase buffered at ketone-water. pH 8.5, only l/lo,oooth of the acid will be in the neutral form Using dodecylamine as a site species, the order of anion in the aqueous phase, and yet almost one-half of that present sensitivity in a nitrobenzene membrane sytem is I- > Br- > in the octanol phase will be the un-ionized species. C1- > F-.$O This is the same order as the partition coefficients Since the difference in log P between the ionic and neutral of the anions measured in that solvent.92 forms of solutes partitioned in other solvent systems is For ideal behavior in a liquid membrane electrode, the likely to be greater than that noted for octanol-water, it is site ion should be almost completely trapped within the even more difficult to directly measure the P values for ions organic phase, resulting in almost negligible exchange of in these systems. For instance, in partitioning codeine co-ion; see Figure 2. Ideal behavior is also dependent upon between CHCll and an aqueous phase 0.1 and 1.0 N in complete dissociation of the site ions in the organic phase, HCl, the assumption was made that in neither case was the and the concentration of site ions at which departure from measured value distorted by any free amine in the organic ideality is noted may be a useful measure of the onset of phase.*Q However, values from Table XVII indicate that the association into ion pairs. Ion selectivity depends only of the free amine would be about 5.0 units log PCHCI~ slightly upon ion mobility and rates of diffusion across phase higher than the hydrochloride, and therefore a pK, - pH difboundaries.94 ference of 5 units (pK, = 6.04; pH = 1) is not sufficient to Like nitrobenzene-water, the chloroform-water system assure that only ion pairs are being partitioned. gives a wide range of P values for the counterions associated It is somewhat unexpected to find the log P for the 4 N + with any large organic ion.95-97 This again raises the question CH3 group lower than that of the 4N+-H group. In this case, of which system should one choose for a hydrophobic paramthe nature of the anion appears to make a small but real eter to be used in correlating biological activity. Perhaps if difference in the log Poctanol value. (For N-hexadecylpyone is investigating electrical potentials in isolated nerve ridinium, A log PBr-Cl = 0.12.) The following A log Paotanol tissue, for example, an ion-selective system might give values values were observed for adding both a methyl group and a which rationalize more of the data. Yet it is widely acceptedg8 positive charge to an amine: that with most drugs the biological response in the intact animal is only slightly dependent upon the nature of the A log P Anion counterion (as long as initial solubility is achieved), and thus Chlorpromazine -5.35 c1a model system which is not ion selective should be preferred. Pyridine -5.00 BrCBH~CW~N(CH& -4.75 IThe distinction between ion-selective partitioning systems and the nonselective systems may be simply that the former The partition coefficient of ions between a nonpolar solvent have aprotic organic phases. In an extensive study of ion and water plays an essential role in the application of these solvation in protic us. aprotic solvents, it has been showngg solvents as liquid ion-exchange membranes for ion-selective electrode~.~O lipophilic anion, such as oleate, dissolved in A the solvent nitrobenzene can serve as the site species; (91) H. Ting, G. Bertrand, and D . Sears, Biophys. J . , 6,813 (1966). (92) J. T. Davies, J . Phjls. Chem., 54, 185 (1950). see Figure 2. In theory, the selectivity among various cations (93) F. Karpfen and J. Randles, Trans. Faraday Soc., 49,823 (1953). is completely independent of the chemical properties of the (94) H. L. Rosano, P. Duby, and J. H. Schulman, J . Phys. Chem., 65, site species and depends solely on the difference in parti1704 (1961).
(89) G. Schill, R. Modin, and B. A . persson, Acta Pharm. Suecjca, 2, 119 (1965). (90) G.Eisenman in Ion Selective Electrodes, No. 314, R . Durst, Ed., National Bureau of Standards, Washington, D . C., 1969, pp 4-8. (95) R . Bock and G. Beilstein, 2.Anal. Chem., 192,44 (1963). (96) R. Bock and C. Hummel, ibid., 198, 176 (1963). (97j R. Bock and J. Jainz, ibd., 1983 315 (1963). (98) A . Albert, Selective Toxicity, 2nd ed, Wiley, New York, N. y . , 19603 P 116. (99) A . J. Parker, Quart. Reo. Chem. SOC.,163 (1962).
is added to convert about 20% to the free base. The automatic titrator is then operated as a pH-Stat, and, when the immiscible solvent is added and stirred, it removes only free base from the aqueous phase. From the ratio of NaOH added prior to the addition of organic solvent, the partition ratio can be calculated. Some solutes with surfactant properties cause troublesome emulsions to form between two immiscible solvents. Usually these can be dispersed by centrifugation or long standing or a combination of both. If this fails, diffusion techniques can be used, although they are distressingly time consuming. This method5*has yielded results consistent with other procedures. It has also been shownS7how a partition coefficient can be calculated from the difference between surface and BuW. interfacial tensions, but the accuracy is probably not better than an order of magnitude. 111. Experimental Methods It has been mentioned that Craig countercurrent distribuBy far the most extensive and useful partition coefficient tion procedures often yield valuable partition coefficient data. data were obtained by simply shaking a solute with two imHowever, for purposes of characterizing or separating a parmiscible solvents and then analyzing the solute concentration ticular substance, it is desirablelo6to work with a partition in one or both phases. However, mention should be made of coefficient near 1. This is often accomplished through the some other fundamentally different techniques. use of mixed solvents. Also, when a clean separation of solute Occasionally the ratio of solubilities in two separate solcompounds is desired, concentrated buffers are used106 to vents has been measured and reported as a partition cogive maximum shift of P with pH. As a result, many of the efficient.lOl This is truly a value of P only at saturation and is partition coefficients calculated from Craig procedures have apt to be quite different from the value obtained under the little comparative value because the solvent is unique or conditions of low solute concentration and with the two because the aqueous phase is at high ionic strength. phases mutually saturated. As seen from Table VIII, A perusal of the literature reveals that many different the amount of water soluble in many solvents can be quite techniques have been employed for the simple problem high and this modifies their solvent character considerably. of mixing and separating the two phases in order to obtain Rather high concentrations of organic solutes are necessary an equilibrium distribution of the solute. Many workers to saturate many solvents. Not only does this make for have used periods of shaking as long as an hour or more. greater solute-solute interactions, but such high concenSuch a lengthy procedure is unnecessary. It has been trations actually change the character of the organic phase foundlD7that simple repeated inversion of a tube with so that one is no longer dealing with, say, butanol as the the two phases establishes equilibrium in 1-2 min. With organic phase but with some mixed solvent. However, if the almost all of the many substances studied by these authors, information desired relates to miscible ~ 0 1 v e n t s , 9 ~then ~ ~~0 equilibrium was reached with 50 inversions. Experience in our there is little choice in the matter. An extensive study has laboratory has shown that about 100 inversions in roughly been made of the solubility ratios of amino acids in a series 5 min produce consistent results. Very vigorous shaking of alcohols, and this should be consulted for experimental should be avoided since this tends to produce troublesome details. l o 2l,o 3 emulsions. The clarity of the two phases is not a dependable Another of limited application is that of criterion of the absence of an emulsion, and therefore a placing a volatile solute such as ethanol in a closed system with centrifugation step is recommended for precise determinations. two other solvents which need not be immiscible. If the conThis cannot be overemphasized. For convenience, partitioning centration of solute is determined in both solutions and if the can be carried out in 250-ml centrifuge bottles fitted with relation between solute activity and concentration is known glass stoppers. In this way centrifugation can be accomplished in one of the solutions, the dependence of activity on conwithout transfer of material. Avoiding cork or rubber stoppers centration in the other can be inferred. This method, which eliminates the possibility that impurities might be introduced resembles solvent isopiestic procedures, can be used at low by these materials or that some substances might be exsolute concentrations. tracted by such stoppers. Since it is desirable to work at low A rapid method which employs automatic titration for the concentrations in each phase (0.01 M or less), small amounts determination of partition coefficients of organic bases beof impurities can cause serious error. tween immiscible solvents has been described. To an aqueous In measuring about 800 partition coefficients between water solution of the base hydrochloride, sufficient standard NaOH and octanol we have usually analyzed the solute in only one phase and obtained the concentration in the other by difference. However, if there is the possibility that absorption (100) R . Alexander, E. C. F. KO,A. J. Parker, and T. J. Broxton, to glass may occur, both phases must be analyzed. Such abJ . Amer. Chem. Soc., 90,5049 (1968). sorption has been found to occur with ionic solutes.lo8Ab(101) B. Wroth and E. Reid, ibid., 38,2316 (1916). that anion solvation by protic solvents decrease strongly in the order F- > C1- > Br- > I- > picrate-, while in aprotic solvents the order is reversed. Even though for this study methanol was used as the standard protic solvent (rather than water) and a ratio of solubilities rather than a partition coefficient measured solvent affinity, these data are quite relevant to this review. They predict the large range and correct order of P values for the above anions in the nitrobenzenewater system and predict a very small range in any alcoholwater system (nonprotic us. protic solvents). The solvation values for cationsloowould predict a smaller protic us. aprotic difference, but the methanol us. dimethylformamide values place them in the expected order : Na+ < Kf < Cs+ < Et4N+<
Reinhold, New York, N. Y., 1943, p 200. (103) T. McMeekin, E. Cohn, and J. Weare, J . Amer. Chem. Soc., 58, 2173 (1936). (104) S. D. Christian, H. E. Affsprung, J. R. Johnson, and J. D. Worley, J . Chem. Educ., 40, 419 (1963). (105) A. Brandstrom, Acta Chem. Scand., 17,1218 (1963).
(102) E. Cohn and J. Edsal, Proteins, Amino Acids and Peptides,
(106) L. Craig, G . Hogeboom, F. Carpenter, and V. DuVigneaud, J . Bid. Chem., 168, 665 (1947). (107) Reference 22, p 159. (108) J. Fogh, P. 0. H. Rasmussen, and K. Skadhauge, Anal. Chem., 26,392 (1954).
A. Leo, C. Hantch, and D. Elklns
sorption may also be a serious problem when working with very low concentrations of labeled compounds (<10-6 M ) . It is quite helpful to estimate the partition coefficient in advance of the determination (see section V). This allows one to make a more judicious estimate of the volumes of solvents to employ. With very lipophilic molecules, for example, it is evident that relatively small volumes of nonpolar solvent must be used or there will be insufficient material left in the aqueous phase for analysis. For example, if a solute is thought to have a P value of 200, and 20 mg was partitioned between equal 100-ml volumes, the aqueous phase would end up with only 0.1 mg. If the analytical procedure has an inherent error of 0.05 mg/100 ml, the P value could vary between 133 and 400. If, however, 200 ml of water and 5 ml of nonpolar solvent were used, the water layer would contain 3.5 mg or 1.75 mg/100 ml and the same analytical accuracy would limit the range of P values from 194 to 206. With good analytical procedures and proper volume choices of solvent, log P values in the range -5 to $5 can be measured. As pointed out in section II.C, many partitioning systems show temperature dependence of about 0.01 log unit/deg in the room-temperature range. Obviously, temperature control is essential for highest accuracy and is most important for the more miscible systems. For most applications, especially as an extrathermodynamic parameter for biological structure-activity relationships, variations due to temperature are hardly comparable to those inherent in the other measurements, and therefore we do not consider it a serious shortcoming that most of the values in Table XVII are simply at room temperature without an estimation of what that might be.
I V . Linear Free-Energy Relationships among Systems

Since partition coefficients are equilibrium constants, it should not be surprising that one finds extrathermodynamic109 relationships between values in different solvent systems. Such an assumption was implicit in the work of Meyer25 and Overton26 who used oil-water partition coefficients to correlate the narcotic action of drugs. Smith46also showed the possibility of such relationships, but Collanders was the first to express the relationship in precise terms. log P 2
=
a log P1
+b
Working with only his own partitioning data, Collander examined only the linear relationship between similar solvent systems. In particular, he showed that eq 32 held between the systems isobutyl alcohol-water, isopentyl alcoholwater, octanol-water, and oleyl alcohol-water. Hansch,O using Smiths data, later extended the comparison of relatively nonpolar systems using CHC13-water for PI and the following systems for Pz: CC14,xylene, benzene, and isoamyl acetate. The most useful relationships for the study of solute-solvent interactions are obtained by defining a reference system and making it the independent variable, PI, in a set of equations of the form of eq 32. Most of the reasons behind our choice of octanol-water as the reference system have already been given, but another practical one is the fact that it is the
(109) J. E. Leffler and E. Grunwald, Rates and Equilibria of Organic Reactions, Wiley, New York, N. Y., 1963. (110) C. Hansch, Furmuco, Ed. Sci., 23,294 (1968).
system with the largest number of measured values containing the widest selection of functional groups. Furthermore, a large portion of these measurements have been made in one laboratory, and therefore should be more self-consistent. It is clearly evident from Smiths data46that, when the nonpolar phases of the partitioning systems differ widely, and especially when the solute sets contain molecules which cannot hydrogen bond along with those which can, eq 32 does not give a good correlation. For example, in comparing benzene-water with octanol-water, 52 assorted solutes give a regression equation with a poor correlation coefficient (0.81) and high standard deviation (0.55). It might seem feasible to place all solutes in the order of a ratio of P values from two standard systems and group them, if possible, on this basis. This can be useful when the objective, for example, is limited to a comparison of Lewis acid strengths by using the ratio of P values between a saturated and unsaturated solvent system, hexane us. p-xylene. 1 1 1 Sanused a similar ratio from the CHC13 and diethyl ether systems to reach some general conclusions about the relative percentage of tautomeric forms of various solutes, but this simplified system failed when applied to certain specific cases. For example, it erroneously predicted a sizable concentration of imino form in a solution of benzenesulfonamide.113 Infrared spectroscopy data114s l6 appear to directly contradict this conclusion. It appeared that the simplest way to make such a separation of solute types was to take the values from a single equation and separate all the minus deviants into one category and the plus deviants into another. After one has done this for several solvent systems, one finds that the strong hydrogen bond donors are the minus deviants and the hydrogen bond acceptors are the plus deviants. The ether-water system is exceptional, for while it also segregates the donors from acceptors, the deviations are reversed. Some work has been done to establish a scale of values for H donors116 and H acceptors,117but these cover only a small fraction of the solutes appearing in Table XVII. A reasonable alternative was to place some of the more common functional groups into general solute classes which would be compatible with the plus deviant and minus deviant catagories as indicated by regression analysis. These classes also had to be compatible with the well-known rules based on the electronegativity and size of the two atoms bound by the hydrogen atom;118 see Table VII. It is to be expected that some changes in molecular structure outside of the functional group will have important effects on H bonding, sufficient at times to change the assigned solute class. Examples of this situation which have been allowed for are seen in no. 5 and 13, but others can be expected also. Whenever a solute molecule contained two or more noninteracting functional groups, each of which would require classification as A and B, we have placed it in the class
(111) R. Orye, R. Weimer, and J. Prausnitz, Science, 148,74 (1965). (112) K. Sandell, Nuturwissenschuften, 53,330 (1966). (113) K. Sandell, Monutsh. Chem., 92, 1066 (1961). (1 14) J. Adams and R. G. Shepherd, J . Org. Chem.,31,2684 (1966). (115) N. Bacon, A. J. Boulton, R. T. Brownlee, A. R. Katritzky, and R. D. Toasom. J . Chem. Soc.. 5230 (1965). _ _ ~ (116) T. Higuchi, J. Richards, S . Davis, A. Kamada, J. Hou, M. Nakano, N. Nakano, and I. Pitman, J . Phurm. Sci., 58,661 (1969). (117) R. W. Taft, D. Gurka, L. Joris, P. von R. Schleyer, and J. W. Rakshys, J . Anier. Chem. SOC., 91,4794, 4801 (1969). (118) G. Pimentel and A . McClellan, The Hydrogen Bond, Reinhold, New York, N. Y., 1960, p 229.
\ I
&
Table VI1
General Solute Classes
Group A H donors
3. Barbiturates
4. Alcohols
5. Amides (negatively substituted, but not
c
di-N-substituted)
6. Sulfonamides 7. Nitriles 8. Imides 9.a Amides
Group B H acceptors
a Classes 9 and 10 must be reversed when considering the ether and oil solvent systems. b E.g., o-nitrophenol. Neutral in CHCh and CC14.
which gave the best fit with that particular equation. It was felt that the best fit of the data would serve to categorize the dominant solvation forces in such cases. For example, pmethoxybenzoic acid is both an acid (class 1) and an ether (class 14). Regression equation A gave the best fit in the solvent systems : benzene, toluene, and xylene (see Table VIII). This suggests that the H-donor ability of the carboxyl group dominates in placing p-methoxybenzoic acid in the most poorly accommodated category when these solvents are compared to octanol. In the CHCls--water system, however, p-methoxybenzoic acid is not so poorly accommodated (again in relation to the standard reference system), and actually the N equation fits it as well as the A (Table VIII). This suggests that the weak H-donor capability of the solvent, CHC18, increases the accommodation of this solute by interacting with the ethereal oxygen. Once a practical basis for sorting solutes was available, we could study the set of equations (of the form of eq 32) relating the solvent systems to see if the slope and intercept values could give some indication of the solute-solvent forces at work. In doing so, it was convenient to establish some sort of preliminary order to the solvent systems. Although the dipole moment, the dielectric constant, the solubility parameter,119-122and the molar attraction constant have each been useful in establishing a scale for solvents in certain applications, none seemed to put partitioning solvent systems into a sensible order. A simple scheme which did work was to order them according to the amount of water they contained at saturation. In Table VI11 they appear in this order. In using the slopes and intercepts of the equations of Table VI11 to study solute-solvent interactions as compared to the standard solute-octanol interaction, we can consider the
(119) J. H. Hildebrand and R . L. Scott, The Solubility of Nonelectrolytes, 3rd ed, Reinhold, New York, N. Y., 1950. (120) L. J. Mullins, Chem. Rea., 54, 289 (1954). (121) S . Khalil and A . Martin, J . Pharm. Sci., 56, 1225 (1967). (122) J. A . Ostrenga, ibid., 58, 1281 (1969).
slope value first. We can see that it is a measure of the solvent systems sensitivity to changes in lipophilicity of solutes. Butanol-water. as expected, has the lowest slope value and the least sensitivity. When this pair is saturated with one another, they are about as much alike as two separate phases can be, Since log P measures the difference in transfer energy between the two, changes in solute character will register as only small differenceswhen compared to octanol. Increasing the hydrocarbon chain length in the solvent alcohol increases the dissimilarity of the alcohol-water phases, and there is an increased sensitivity to solute changes. Apparently, a maximum sensitivity is reached at octanol for the slope in the oleyl alcohol equation is also 1.0. There is some basis for the postulate that the partitioning process, outside of hydrogen bonding, is the same for solutes in each system, and therefore if hydrogen bonding were accounted for separately, the slopes of all the equations in Table VI11 would be near 1.0. Some of the results reported by Higuchi and his coworkers l6 can be interpreted in this manner. They have used the cyclohexane-water system where the organic phase has a minimum of hydrogen-bonding ability, and to it have added a small amount of tributyl phosphate (TBP) or isopropoxymethyl phosphoryl fluoride (sarin) as H-bond acceptors. By partitioning a set of substituted phenols between the two phases they have calculated an equilibrium constant for the solute-TBP complex. Table IX contains values for the phenols, and from their data and log Poctanol it eq 33 and 34 have been formulated. The correlation belog Pootsnol
=
0.50 log Poyolohexane n r S 9 0.791 0.391
+ 2.43
(33)
log Pootan01 = 1-00 log Pcyolohexane f 1.20 log K n H n r S 9 0.979 0.140
+ 2.35
(34)
tween partition coefficients in octanol and cyclohexane is poor, as shown by eq 33. However, when correction is made for the hydrogen-bonding ability of the phenols by adding a term in log K H ~a, good correlation is obtained (eq 34). Moreover, the coefficient with log Poyolohexane is 1.00, indicating that in a rough sense the desolvation processes are the same for each system. It is reasonable to propose that decreasing the lipophilic character of the nonaqueous phase decreases the energy required to transfer a hydrocarbon solute (or a specific segment of a solute, such as a methylene group) from the nonaqueous to the aqueous phase, and this would result in a decrease in the slope values in Table VI11 in going from octanol to butanol. It would be logical to predict, therefore, that any alteration of the aqueous phase in these partitioning systems to make it more like the nonaqueous would also reduce the transfer energy and lower the slope. There are not a great deal of data in the literature which are suitable for testing this hypothesis, but the investigations of FeltkamplZ5certainly support it. He measured the distribution of various barbiturates between diethyl ether and a 50:50 mixture of dimethylformamide and water. Since DMF itself is not very well accommodated by ether (log Pether-water
(123) P values for ail of the solutes used to develop the equations are listed in J. Org. Chem., 36, 1539 (1971), microfilm edition. (124) D. Burton, K . Clark, and G. Gray, J. Chem. SOC., 1315 (1964). (125) H. Feltkamp, Arzneim.-Forsch., 15,238 (1965).
Table VIIl
Solvent Regression Equations1e8
LogP.oiv = a LogPootsnoi b
-H20 coneti at saturationSolvent

(VS. HoO)
I08M
a5
H-donor solutes Equation A---ba n r
r--
H-acceptor solutes Equation B-------, b n r
Cyclohexane Heptane CCIP xylene Toluene Benzene CHC13C Oilsd Nitrobenzene Isopentyl acetate Ether
2.5 3.3 10.0 18.8 25.6 26.0 68.4 72.5 180 456 690
0.675 - 1.842 (k0.24) (k0.48) 1.056 - 2.851 (k0.73) (11.46) 1.168 - 2.163 15) (k0.12) (k0. 0.942 - 1.694 ( i o . 13) (k0.21) 1.135 - 1.777 (k0. 11) ( 1 0 . 16) 1.015 - 1.402 ( 1 0 . 11) (k0.14) 1.126 - 1.343 (k0.12) (f0.21) 1.099 - 1.310 (k0.06) (k0.09) 1.176 - 1.072 (10.23) (10.20) 0.072 1.027 ( i 0 . 0 8 ) (10.13) 1.130 - 0.170 (k0.04) (k0.05)
26 10 24 19 22 33 28 65 9 22 71
0.761 0.764 0.974 0.963 0.980 0.962 0.967 0.981 0.977 0.986 0.988
0.503 0.916 0.282 0.225 0.194 0.234 0.308 0.271 0.217 0.209 0.186
1.063 - 0.734 (k0.12) (10.25) 1.848 - 2.223 (k0.44) (k0.93) 1.207 - 0.219 (k0.27) ( i 0 . 3 7 ) 1.027 - 0.595 (f0.08) (k0.16) 1.398 - 0.922 (f0.22) (k0.37) 1.223 - 0.573 (kO.19) (f0.20) 1.276 0.171 (k0.14) (k0.17) 1.119 - 0.325 (k0. 11) ( 1 0 . 19)
30 11
11
0.957 0.954 0.959 0.986 0.971 0.958 0.976 0.988
0.360 0.534 0.347 0.230 0.274 0.291 0.251 0.233
21 14 19 21 14
1.142 - 1.070 (10.13) (10.12)
32
0.957
0.326
Oleyl alcohol Methyl isobutyl ketone Ethyl acetate Octanol Cyclohexanone Primary pentanols
see- and tertpentanols 2-Butanone
712 950 1620 2300 4490

50006
5320, 5460 6510 9440.
Cyclohexanol Primary butanols
0.999 - 0.575 (k0.06) ( 1 0 . 11) 0.050 1.094 (i0.07) (fO.ll) 0.932 0.052 18) (h0.21) (k0. 1.000 o.oO0 1.035 0.896 (f0.20) ( f 0 . 30) 0.808 0.271 (3~0.07) (kO.09) 0.892 0.288 (10.06) ( i 0 . 0 6 ) 0.315 0.493 (k0.07) (k0.07) 0.866 0.745 14) (iO.09) (k0. 0.381 0.697 (k0.02) (10.03)
Sole Equation 37 0.985 0.225
+ + + + + + + + +
17 9 10 19 11 9 12 57
0.993 0.969 0.972 0.987 0.996 0.987 0.985 0.993
0.184 0.202 0.340 0.161 0.091 0.093 0.100 0.123
The N equation is log PCCU = 0.862 (f0.60) log Pootanol - 0.626 a The values in parentheses are the 9 5 z confidence intervals. (rt0.70) (n = 6, r = 0.809, s = 0.462). c The N equation is log PcBCll = 1.10 ( i O . 0 9 ) log Pootsnoi 0.617 (10.12) ( n = 32, r = 0.974, s = 0.254). d Most liquid glyceryl triesters fit this equation; olive, cottonseed, and peanut oils were the most frequently used. E n-Amyl alcohol = 5.03 M in water; isoamyl alcohol = 4.50 M in water. f Water content measured for 2-pentanol only. 0 Water content measured for 1-butanol only.
= -1.62),2 it should not greatly change the solvent properties of the water-saturated ether phase, but it must greatly reduce the protic nature of the aqueous phase. The following equation was derived using this rather limited set of solutes.
log Pethei/H20-DMF = -0.321 0.400 log Pootanol n r S 6 0.988 0.058 The equation with two additional values for hexobarbital and phenobarbital was essentially the same (slope = 0.405)
even though these poorly predicted solutes lowered the value of r to 0.86. It is apparent that this drastic reduction in the protic character of the aqueous phase has reduced the sensitivity of the ether-water system to changes in lipophilicity of solutes by a factor of 2.8 (i.e., 1.13/0.4). Diethylformamide, by disrupting the water envelope around a nonpolar solute, in all probability reduces the entropy factor in phase transfer. The intercept value for each of the regression equations in Table VI11 can be used as a measure of the lipophilicity of the solvent in a slightly different fashion. It is apparent that the intercept value in the equation for a given solvent system
Chemical Reviews, 1971,Vol. 71, No. 6 541
Table
IX
Relationship between Phenol Partition Coefficients in Octanol and Cyclohexane

Pheriol
Log
Payalohexsnea
ObsdC C a M d Log Log Log K E B ~ Poctanol Pootanoi IA bgpl

0.00 -0.16
-0.11
Unsubstituted 4-Me
4-Et 4-tert-Butyl 3-F
4-F 4-C1
4-NO2 2,3-(CH)r
-0.85 -0.14 0.40 1.12 -0.85lz4 -1.00 -0.70124 -1.93 0.52
-0.27 0.39 0.24 0.48 1.33 0.16
1.46 1.94 2.44 3.31 1.93 1.77 2.39 1.96 2.98
1.50
2.02 2.62 3.15 1.97 1.64 2.24 2.01 3.06
0.04 0.08
0.18
0.17
0.04 0.14 0.16

0.05
0.08
a Some values are average of two determinations; see Table XVII. b From ref 117. c From ref 10 and 58. Calculated using eq 34.
is the log P for any solute which is distributed equally between water and octanol; i.e., log Poctanol 0. Thus a nega= tive intercept for any equation indicates that the solvent is more lipophilic than octanol, and a positive intercept indicates that it is more hydrophilic. This is more readily apparent if one examines a homologous series of solutes, for example, the carboxylic acids. The octanol log P values begin at -0.54 for formic and rise to -0.17 for acetic and to +0.33 for propionic. Therefore, it takes between two and three lipophilic methylene groups to balance the hydrophilic carboxyl group and allow the octanol to share the solute equally with water. In the oleyl alcohol-water system, it takes one additional methylene group before a carboxylic acid becomes lipophilic enough to be equally shared; i.e., log Poleyl = 0 between ala propionic and butyric. Similarly, it is noted that in nitrobenzene-water it takes two additional methylenes, in benzenewater it takes three, and in CCI4-water it takes about 4.5 additional groups to bring the solute to an equal lipophilic level with the organic phase. Using the intercept values from the A or sole equation as a measure of the solvents lipophilicity, we see that there is a very good correlation between these values and the water content at saturation. log (H20) = 1.077[intercept]
n r
S
represents the per cent of small molecules partitioned onto the protein, while F is the per cent of small molecule in the aqueous phase. A number of such examples are given in Table X. In other examples the binding constant is expressed as 1/C where C is the molar concentration of small molecule necessary to produce a 1 :1 (or higher, as indicated) complex of protein and small molecule. The way the binding constant is defined greatly affects the intercepts listed in Table X so that only those defined in the Same way can be compared. The slopes, however, differ very little regardless of the system, the type of compound studied, or the way in which the binding constant is defined. Omitting the slopes for examples 1, 2, and 9 where the work was done at 4 O (since it is known the slopes for the Hammett-type relationships are higher at lower temperatures), and omitting the rather deviant value of example 12, we are left with a set of 14 slopes with a mean value and stan0.06. This is amazingly constant condard deviation of 0.55 =t sidering the variations in conditions. The relationship between the results in Table X and those of Table VI11 calls for further careful analysis. None of the slopes in Table VI11 are as low as 0.54; the lowest for a carefully studied system is that of the butanols (0.72). In this sense, butanols behave more like the proteins than the other solvents of Table VIII. In fact, Scholtan130has shown that the binding of many drugs to serum protein follows the relationship log K = 0.9 log P~-BoH constant
(37)
+ 0.249
(35)
17 0.979 0.217 Sometimes it may be misleading to think of a scale of lipophilicity as the simple reciprocal of a hydrophilicity scale, but eq 35 shows that the inability of a partition solvent to accommodate water is a good measure of its lipophilic behavior toward a great assortment of organic solutes. A more complex kind of partition, but one which can be studied by means of linear regression equations similar to those in Table VIII, is that of the distribution of small organic molecules between proteins and an aqueous phase. A large number of such examples are known which can be correlated by an equation similar to eq 32. (36) In eq 36, K is an equilibrium constant measuring the binding of the small solute molecule by protein. In some work, the expression log (B/F) has been used instead of K . B log K
=
In eq 37, there is almost a 1:1 relationship between the logarithms of the two kinds of equilibrium constants. In this limited sense butanol, saturated with water, resembles a protein in structure. Of course, in actual fact, saturated butanol which contains a greater number of water molecules than butanol molecules, is not at all like a protein. If the main driving force in the transfer from water into octanol or onto a protein is desolvation of the water about the solute, then we can postulate that the degree of desolvation must be about the same in each process. In the case of butanol, the solute molecule, in entering the butanol phase, finds itself in a rather aqueous environment. While the structure of the flickering clusters around the solute must be largely broken up in butanol, more such structures must be present than in solvents such as octanol or benzene. In the case of the proteins of Table X, since term the weighting factor with the log Pootanol is 0.5, one could postulate that only half as much desolvation occurs on the average in partitioning onto a protein as into octanol; that is, for a given increment in hydrophobicity (say, a phenyl group), the driving force for partitioning onto protein is only half of that of partitioning into octanol. One way of rationalizing this is to postulate that the solute molecules are partitioned onto the surface of the protein and in this way only partially desolvated. This seems a more logical explanation than to assume that they are completely engulfed by protein
a log P
+b
(126) C. Hansch in Drug Design, Vol. 1, E. J. Ariens, Ed., Academic Press, New York, N. Y., 1971, p 271. (127) A. E. Bird and A. C. Marshall, Biochem. Pharmacol., 16, 2275 (1967). (128) C. Hansch and F. Helmer, J . Poiym. Sci., Part A-1, 6, 3295 (1968). (129) J. M. Vandenbelt, C. Hansch, and C. Church, unpublishedresults. (130) W. Scholtan, Armeim.-Forsch., 18, 505 (1968).
Table X Partitioning of Organic Compounds between Proteins and Aqueous Phases
Type of compound
Macromolecule"
K t
1/C 1/C 1/C B/F K 1/C B/F K 1/C K K K
b
,
Ref
T , "C
1. Miscellaneous 2. Miscellaneous 3. Barbiturates 4. Barbiturates 5. RCOO6. Miscellaneous 7. Penicillins 8. Thyroxine analogs 9. Miscellaneous 10. ROH 11. Acetamides 12. Acetanilides 13. Barbiturates 14. Barbiturates 15. Barbiturates 16. Barbiturates 17. Barbiturates 18. Barbiturates
BSA(1:l) BSA (3 :1) BSA (1:l) BSA BSA BSA(1:l) Human serum Albumin Hemoglobin Ribonuclease Nylon Rayon Liverd Heartd Kidneyd Lungd Braind Muscled
0.75 0.59 0.58 0.51 0.59" 0.67 0.490 0.46O 0.71

0.50
B/F B/F B/F B/F B/F B/F
0.69 0.84 0.52 0.62 0.53 0.56 0.52 0.48

=
2.30 2.03 2.40 -1.22 -6.51 2.48 -0.63 2.59 1.51 -1.56 -7.16 -7.24 -1.14 -1.48 -1.42 -1.50 -1.44 -1.45
42 16 4 17
5
0.960
0.900
25 79 8 17 4 7 7
5 5
5 5 5 5
0.961 0.896 0.966 0.945 0.924 0.950 0.950 0.999 0.961 0.967 0.973 0.950 0.962 0.956 0.973 0.970
0.159 0.133 0.137 0.181 0.213 0.242 0.134 0.237 0.160 0.012 0.203 0.227 0.124 0.207 0.152 0.173 0.125 0.121
9 9 9 126 9 129 127 126 9 9 128 128 126 126 126 126 126 126
4 4 RT RT 23 37 -22 37 4 62 26.5 26.5 RT RT RT RT RT RT

?r
a BSA = bovine serum albumin. * C = molar concentration; B/F used instead of log P. d Homogenized.
ratio bound to free; for definition of K,see original article.
values
(as they are in passing into butanol) but that the "sweater" of outer molecules is not completely stripped from the solute. There are instances in which the slope relating binding to is 1. log Pootanol For example, the correlation of log 1/Kmwith log P for chymotrypsin substrateslal and inhibitors is essentially 1 for substituents thought to be binding in the pz area. K, is the Michaelis constant and is an approximate binding constant. Chymotrypsin is known to contain a deep cleft which may constitute the p2 area and, in this instance, complete desolvation of the substituent may occur.
x is the logarithm of the partition coefficient of the function
X.For example, A C could be obtained as follows. ~

ACI
= log
Pchlorobenzene
- log Pbenzene
B. SUBSTITUENT FREE ENERGIES AND INTERACTION TERMS

It has been found that x values are relatively constant from one system to another as long as there are no special steric or electronic interactions of the substituents not contained in the reference system. For example, it has been found that A C H ~ for groups attached to various benzene derivatives has a value in the octanol-water system of 0.50 =k 0.04 for 15 different examples. The weak interaction of the methyl group with functions as active as a nitro group is exceptional. Most other x values are not so constant with respect to electronic environment. For example, in 15 examples of xNo2in aromatic systems, A had a mean value and standard deviation of 0.01 f 0.32. The function A is best viewed in extrathermodynamic terms. The symbols H-N-H and X-N-H can be used to represent a solute nuclei (N), the first one unsubstituted and the other containing the substituent X. The parameter A can then be defined by a comparison of two equilibria H-N-H H X-N-H
H
KI
V . Additive-Constitutive Properties
It was apparent to MeyerZ5 and Overton,2eas well as the other early workers in the field, that in a homologous series the partition coefficient increased by a factor of from 2 to 4 per CH2. Cohn and Edsallo2verified that this kind of additivity held for the solubility ratios of amino acids in ethanol and water. They also extended it to include values for the groups -CH2CONH-, OH, SH, and CsH6, and for dipolar ionization. Collander4 determined that AP/CH2 fell in the range of 2 to 4 for the ether-water system and 1.8 to 3.0 for the butanol-water system. He also reported a range of values for A P when the following substitutions were made: OH for H, NH2 for H, CO2H for CHI, C02H for CONH2, and halogens for H. In view of these long-standing observations, it is surprising that no really systematic effort was made to study the additive character of the partition coefficient until the early 60's.
L H-N-H
KI = (H-N-H)L/(H-N-H)H
A. DEFINITION OF x
Additivity was first established for a wide variety of groups in a study of the substituent constant, x , definedloin an analogous fashion to the Hammett u constant
x x = log Px
L e X-N-H
~z
Kt = (X-N-H)L/(X-N-H)H
The superscripts H and L denote the hydrophilic (H2O) and lipophilic (solvent) phases and refer to the phase in which the molecule is located.
A
- log P*
log K2IKi
where PXis the derivative of a parent molecule, PH, and thus

(131) C.HanschandE.Coats,J.Pharm. Sci., 59,731 (1970).
That is, the ratio of the equilibrium constants is equivalent to the equilibrium constant for the reaction X-N-IIH
+ H-N-HL e X-N-HL + H-N-HH
(38)
The free energy change resulting from the introduction of X on the first of the above equilibria would be 2.3RTlog K?lKl = Gx-N-HL
+ GH-N-HH Gx-N-HH
- GH-N-EL (39)
If we assume that the free energy of an individual molecule in eq 38 can be represented as the sum of its parts and their interaction, we may write
Gx-N-HL
=
GxL
+ CNL + GHL +
GXNL
+ GHNL+ GXHL
(40)
In eq 40, the terms on the right represent the free energies of the substituents X or H and their interactions with the basic structure N (GXNL) or each other (GXHL). Formulating the other molecules in this fashion and substituting into eq 39 yields 2.3RT log K ~ I K = GxL I
Gx&
extended indefinitely and that, for the present, one is limited to the use of model systems wor!.ing outside of classical thermodynamics. It has been shown10 that the difference in A constants from two different systems is highly dependent on electronic interactions. This is illustrated by eq 48-51 in which the Hammett function,logu,is the measure of electronic interaction. A good correlation is obtained with phenols in eq 48. The positive coefficient with u indicates that an electron-withdrawing substituent, X, will be relatively better accommodated by octanol when it is moved from benzene to phenol. Surprisingly enough, a poorer correlation is obtained using u-. The reason for this may be that the linear relationship between Air and u does not cover a very wide range of u values. For example, placing two nitro groups on phenol yields a negative AT rather than a positive Air obtained for mononitro functions in eq 48.
+ GXNL+ + GaH + GHNH+ G H ~ - GxH H

GHNL
1. Inductive Efect
Relatively little systematic effort has been expended studying systems in which the inductive effect of one substituent on another can be cleanly dissected away from other effects. It is clear in the benzyl alcohols correlated by eq 49 that electron-withdrawing substituents increase log P values relative to benzene. For example
GXNH- GXHH - GHL -
- GHHL
(41)
Making substitutions of the type GXL - GXH = AGx, eq 41 is converted to 2.3RT log KyjKI
=
AGx
+ AGXN+
- AGH
(43)
AGXH- AGH - AGHK- AGHH (42)
If the interaction terms can be neglected, then

T
= 2.3RT log K ~ I K = AGx I
When two functions are involved, the following equilibria must be considered.
H K3 L H-N-Y H-N-Y K3 = (HLN-Y)~/(H-N-Y)~
e e
K4
(44)
X-N-Y X-N-Y Ka = (X-N-Y)L/(X-N-Y)H
(45)
Equation 46 can then be derived from eq 44 and 45.

i r
= 2.3RT log K4/K3 = AGx
+ AGXN+
(47)
AGXY - ACHY - AGH - AGBN (46)
Subtracting eq 43 from 46 yields

AT
=
AGXY
+ AGHH- AGHY- AGXH

Air = AT = Air = Air
=
Rphenol
In this example it seems unlikely that the primary effect on i r is the action of CHzOH on NOz; it seems more reasonable to assume that the electron-withdrawing action of NOz on the region near the OH function is responsible for Air of 0.39. The inductive effect of the nitro group which is insulated from the OH by the CHz unit is apparently making the lone-pair electrons of the OH function less available for hydrogen bonding lowering the affinity of this function for the water phase. This same effect is quite apparent with anilines and phenols bearing electron-withdrawing functions. While the inductive withdrawal of electrons from the region of a function conr taining lone-pair electrons often raises its i value, this is not always so. i r c l from the benzene system is 0.71, while ir&C1 in the nitrobenzene system is only 0.54, and ir3.c1 is 0.61. That the inductive effect is quite small with alkyl groups is illustrated by eq 52 and 53.
irbenzene
0 . 8 2 ~ 0.06
= 0 . 4 7 ~ 0.04 f = 0 . 3 6 ~ 0.04
24 0.954 0.097
r b e n z y l alo
Tbenzene
11 0.937 0.086
22 0.754 0.100 20 0.676 0.250
irphenaxyacetic acid Tnitrobenzene
sbenzene
Tbennene
- 0 . 5 1 ~f 0.28
TCH~
For Air to equal or approach 0, the four interaction terms must be equal to or approach 0. (There is of course the unlikely case where they might cancel each other so that AT = 0.) As the number of changes in the systems under comparison becomes larger, so do the interaction terms, and hence r the possibility that i from very different systems will remain constant becomes less likely. It is apparent from this analysis that the approach of Cratinsl (see section 1I.C) cannot be
log PEtNOZ - log P M ~ N O ~ = 0.18 - (-0.33)

=
= =
0.51 (52) 0.47 (53)
rcHz log PPrNO2log P E t N O 2 = -
0.65 - 0.18
2. Resonance Eflect
The effect of electron delocalization on
i r
values is well illus-
trated by the difference between aliphatic and aromatic T values shown in Table XI. The effect of moving functions from
that T-CH-CH- is the same in one of the conjugated double bonds in naphthalene as in an isolated double bond in 5hexen-2-one. An acetylenic group has a somewhat lower i value. r
T-CICH
Table XI Comparison of Aromatic and Aliphatic

Log PC6HaX Function Aromatic K
Values
AT
Tar
= log
=
log PCtiH6
-1.23 1.12 0.61 -0.55 -1.49
Log P R X log PRH

-1.19 1.00 0.45 -0.71 -1.71 -0.27
Aliphatic
?r
T-CECH
- log P c ~ H ~1.98 - 1.50 = log P C ~ H ~ ClogC H = 2.53 - 2.13 - ~ Pcsao

Pi-pentyne
= =
0.48 0.40
Tal
-0.01 0.86 -0.57 0.14 0.71 -0.28 -0.02 2.08 0.18 -0.67 -0.28
0.60
-0.84 -0.17 0.39 -0.67 -0.47 1.61 -0.30 -1.16 -0.85
-0.04 0.12 0.16 0.16 0.22 0.26 0.26 0.27 0.31 0.32 0.39 0.45 0.47 0.48 0.49 0.57
Conjugation of ir-electron systems does not appear to result in big changes in T values even when a heteroatom is included in the system. Table XI1 illustrates the amount of variance in Table XI1 Constancy of T for -CH=CHCH=CH"-CH-CHCH-CH-
1.39 1.38 1.43 1 . 37 1.45 LOgPbeneothiophene - I o g P t h i o p h e n e = 3.12 - 1.81 = 1.31 L O g P n s p h t h a l e n e - 1 0 g P b e n r e n e = 3.45 - 2.13 = 1.32 1.42 '/I log Pbeneene = '/1(2.13) = 1 .38 Log Po-nspbthol - b g P p h e n o l = 2.84 - 1.46 =
Log P i n d o l e - log Ppyrrole = 2.14 - 0.75 = Log Pquinoline - log P p y r i d i n e = 2.03 - 0.65 = log Pisoquinoiine - log P p y r i d i n e = 2.08 - 0.65 = Log Paoridine - log Pquinoline = 3.40 - 2.03 = LOgPdibenzofuran - 1ogPbenzofuran 4.12 - 2.67 =
Log Po-naphthoxyaoetio
aliphatic to aromatic positions is a complex one. The amino group stands out by showing the smallest change, this despite the fact that a large amount of evidence leaves no doubt about the delocalization of the nitrogen lone-pair electrons. The higher T value which should result from this effect is apparently offset by better hydrogen bonding of the two hydrogen atoms which increases affinity for the water phase. When the hydrogen atoms are removed, as in the N(CH& function, we see the expected Air value, that is, one somewhat higher than ATOCH~. With the more electronegative oxygen atom this effect is not observed. The largest Air is for NOn, and it appeared possible that the acidity of the a-hydrogen atoms might be playing a role in conferring unusual hydrophilic character to the aliphatic nitro solutes. However, T N O ~ was found to be essentially unchanged for the tert-nitro derivative, 2-methyl-2-nitropropane. With the exception of NH2, transferring any function from an aliphatic to an aromatic position results in an increase in lipophilicity. Actually, AT for NHz is so small that it can be considered to be 0. Replacing a single bond with a double bond results in a constant AT of about -0.3. This can be illustrated as follows by comparing T - C H ~ C H ~ - (= 1.OO)with T-CH-CH- derived from five systems (Chart I). If, indeed, log P or T is primarily
2.54
- 1.21 =
aoid
- log Pphenoxyaoetio m i d
1.33
~
AV = 1.38
j 0.036 =
T-CH-CHCH-CHin a variety of different aromatic systems. The mean value and standard deviation for the 10 systems is 1.38 i 0.036.
3. Steric Effect
Steric effects can be quite varied in nature. The shielding of lone-pair electrons by inert alkyl groups produces a significant increase in T values.
TCHs
log P2-methylphenoxyaoetio
aoid
- log P P O A - log P P O A
= =
2.10 - 1.26
TCHs
0.84
= log
P3-methylphenoxyaoetic acid
1.78 - 1.26 = 0.52 Shielding a hydroxyl function by inert groups such as 2,6substituted phenols reduces hydrogen bonding and results in a positive AT. This is most pronounced in the case of a nonpolar solvent system such as cyclohexane. 132,133 Crowding of functions may also reduce hydrophobic bonding with the opposite effect on AT. For example, pentachlorophenol has a measured log P of 5.01, while its calculated value would be log P
=
0.73 0.71 0.69
phenol
~X,-CI
~T,-CI
1.46
+ 1.38 + 2.08 + 0.93 = 5.85
X=-CI
Av
0.73
AT = -0.27
Assuming electronic effects of each C1 atom to be contained in the corresponding i r c ~value, A a s t e r i o = 5.01 - 5.85 = 0.84. Presumably, this would be the result of fewer water
(132) C. Golumbic, M . Orchin, and S. Weller, J . Amer. Chem. SOC., 71, 2624 (1949). (133) J. Fritz and C. Hedrick, Anal. Chem., 37, 1015 (1965).
determined (in apolar functions) by the removal of an envelope of structured water molecules, then it is not surprising
molecules clustered around each chlorine atom in the pentachloro derivative than in the monochloro derivatives. 1,2,3-Trimethoxybenzene is an interesting example of how the steric effect can operate to inhibit resonance and thus decrease A. log P c ~ H ~ ( = c H P ) ~ H ~ H O C H ~2.13 o log ~ c ~ ~ =
- 0.06
= 2.07
The measured value is 1.53, indicating greater than expected affinity for the water phase. If we assumed that only the central OCH3is perturbed and that it is twisted out of the plane of the ring so that resonance between the oxygen lone pair electrons and the A electrons of the benzene ring is prevented, then the central OCHI might be expected to have the A value of an aliphatic function. This can be tested as follows.
AOCHa
log Pl,2,3-trimethaxybensene log P1,3-dimethoxybenzene

=
1.53 - 2.09 = -0.56
The A value for the twisted -0CH3 (-0.56) is much closer to that of an aliphatic OCHI (-0.47) than it is to an ordinary aromatic -0CH3 (-0.02). Sometimes the steric effects of alkyl functions on the solubility characteristics of an adjacent carbonyl function can be quantitatively correlated with the Taft E, parameter. The partition coefficients of a series of 2-alkyltriazinones are listed in Table XI11 along with E, values. The calculated log P values
Table XIII Steric Effect in Triazinones

0
Another instance in which chain branching results in hydrophilic shielding and increases log P (contrary to an expected negative AT as explained in the following section) has been reported135 in the study of a series of dialkylphosphorodithiotic acids. Branching apparently also increases the acid dissociation constant, an effect which would not be expected from electronic forces alone. Steric shielding of a tertiary nitrogen apparently explains the difference in the partition coefficients between the all0 (planar and hindered access to N) and epiallo (N exposed at bend) isomers of corynantheidinetype alkaloids. In the heptane-water system, the A A for the allo-epiallo transition is f1.07 in one instance and +0.76 in another. However, it is not clear from the proposed structural formulas why there should be a much lower AT comparing the normal (planar) with the pseudo (nonplanar) in two other examples [Aa(speciogynine - mitrociliatine) = SO.11; Aa(dihydroc0rynanthine - hirsutine) = +0.11]. Some care must be exercised in deciding whether a difference in observed partition coefficients between stereoisomers is truly the result of the balance of hydrophilic-lipophilic forces. For example, P values have been measured13 in benzenewater for the exo (P = 2.37) and endo (P = 4.23) epimers of an analog of meperidine. However, the aqueous phase was buffered at 7.4 and, since the exo form is more basic (pK, = 8.35 us. 8.19), there is a lower percentage in the un-ionized form. The corrected P values are exo = 29 and endo = 30. The observed lower biological activity of the exo epimer stems from its pK,.
4. Branching
A normal aliphatic chain usually has a higher A value than a branched chain. For example, 7r3-pr = 1.45 and ~ 3 - i - p = ~ 1.33 in the phenoxyacetic acid system. When branching occurs at the functional group, the effect appears to be slightly greater; e.g., tert-BuOH = 0.37,2-BuOH = 0.61, and 1-BuOH = 0.88. Similarly, log P ~ - P ~ N0.03 while log Ppr~a2 = H~ = 0.31. In contrast to this, however, there seems to be no difference between log P for isopropylbenzene and propylbenzene. Also, there appears to be no lowering of log P in tert-butylbenzene. The observed value of 4.11 is what would be expected for the n-butyl derivative if calculated from the value of 3.68 for propylbenzene. Accepting the fact that some discrepanices remain to be resolved, we have, for the purpose of calculating log P values, tentatively used the value of -0.20 for branching.
No.
1. 2.
logpa
Calcd
E,
0.00 -0.07 -0.36 -0.47 -0.93 -1.54 -0.35 -0.79 -0.40
Obsd
logP
pred Obsd by eq 54 pred

~~~
Log P
3.
4.
5.
6.
7.
8. 9.
Talk
CH3 -0.16 C2H5 0.34 n-C3H7 0.84 i-C3H, 0.64 i-CaHg 1.14 ferf-C4Hg 0.94 i-C5Ho 1.65 C-C&1 1.81 n-C~H13 2.35
-0.16 0.46 0.93
1.01 1.39 1.70 1.85 2.14 2.68
-0.14 0.41 1.04 0.88
-0.02
0.05
-0.11 0.13
1.57 1.60
1.85 2.19 2.59
-0.18 0.10 0.00
-0.05
0.08
The methyl derivative used as the parent compound and from either the phenoxyacetic acid or benzene systems used to calculate the normal log P values of the remaining compounds.
5 . Conformational Efects
Another problem which must be taken into account in the additive-constitutive character of log P is the conformation of organic compounds in solution. It might be expected that when aliphatic chains become long enough, they would tend to coil up in solution with the formation of molecular oil droplets. With simple molecules such as monofunctional straight-chain aliphatic compounds, clear-cut evidence seems to be lacking for such balling-up of chains. In fact, it ap-
are those expected from the addition of T a l k y 1 to unsubstituted triazinone. It is apparent that the observed values of Draber, Buchel, e f aI.,134 are higher. Equation 54 rationalizes this difference in terms of E,. log P o b s d = 1.026 log Pealed - 0.392Ee f 0.024 n r S 9 0.993 0.018 (54)
(134) W. Draber, K. Buchel, K. Dickore, A. Trebst, and E. Pistorius, Progr. Phoiosyn. Res., 3, 1789 (1969).
(135) R. Zucal, J. Dean, and T. Handley, Anal. Chem., 35,988 (1963). (136) A. Beckett and D. Dwuma-Badu, J . Pharm. Pharmacol., 21, 162s (1969). (137) P. Portoghese, A . Mikhail, and H. Kupferberg, J . Med. Chem., 1 1 , 219 (1968).
pears that it will be quite difficult to disentangle this phenomenon from that of premicellular interactions. If balling-up of an aliphatic chain occurred, one would expect the number of water molecules held in the flickering cluster around such a ball to be much less than the number held around the extended chain. This would mean a lower desolvation energy on phase transfer and, hence, a lesser increment in partition coefficient-possibly an abrupt discontinuity in A log P as one ascends a homologous series. A clear example of such changes in partition coefficient as one ascends a homologous series is lacking. In the RCOOH series, normal behavior occurs up to decanoic acid. av T/CHZ = l/S(log P C ~ H ~ ~ C O PCH~COOH) - log O H = 0.53 However, AT between decanoic and dodecanoic acid is much smaller than the 1.0 unit expected in terms of simple additvity. The log P values for dodecanoic acid were determined using IC-labeled material. Great difficulty was experienced in obtaining reproducible results, and considerable uncertainty surrounds the value of 4.20 for dodecanoic acid. Whether this unexpectedly low value is due to a folding up of the aliphatic chain or a premicellular tail-to-tail dimerization remains an open question. Other solvent systems also produce a constant increment in log P per -CHz- group for fatty acid homologs. 1 3 8 This increment is about 0.6 in the heptane-water system for valeric through myristic acids. 139 The alcohol homologous series also shows the expected increase in log P with the addition of each CHZunit. In this series
Table XIV
Effect upon H of Folding of Alkyl Chains

Function
TI
TZb Ti
Hz
OH
F
c 1
Br I COOH COOCH3 COCH, NHz CN OCHa CONHz
-1.80 -0.73 -0.13 0.04 0.22 -1.26 -0.91 -1.26 -1.85 -1.47 -0.98 -2.28
-1.16 -0.17 0.39

0.60
0.64
1.oo -0.67 -0.27 -0.71 -1.19 -0.84 -0.47 -1.71
0.56 0.52 0.56 0.78 0.59 0.64 0.55 0.66 0.63 0.51 0.57
AV = 0.60& 0.05
Log P c ~ H ~ ( c H ~log x c ~ H ~ ( c H Log PRX - log PR. - )~ P ~)~H. R is a normal alkyl group of four carbon atoms or less.
a T/CHz V
/lI(lOg Pdodeoanol - log Pmethanol) = 0.52
there was some difficulty in obtaining constant log P values over a wide concentration range for alcohols of greater chain length than CI?. In summary, it would seem that molecular oil droplet formation does not occur with simple aliphatic compounds 1. before c 4 If folding does not occur up to CM,it would imply that there is an inherent stability in the aqueous phase of the aliphatic chain caused, perhaps, a by a restriction of rotation around each C-C bond as Aranow and Witten proposed?g The situation is of course much different when more than one reactive center is present per molecule. It appears that folded conformations of many organic compounds in aqueous solution can be detected through partitioning studies. This is well illustrated by a study of derivatives of the type GH6CHZCHZCHZX. When X = H, log P was found to be 3.68 which is quite close to the calculated value: log Pbeneene ~ T C H= 2.13 ~ 3(0.50) = 3.63. Other mixed aliphatic-aromatic compounds also give good agreement between calculated and observed values. However, in comparing T values
turn out to have a greater affinity for the aqueous phase than one would expect from the corresponding aliphatic functions. Most surprising was the fact that AT for the two systems was essentially constant regardless of the kind of function compared. It was suggested that this greater than expected aqueous solubility of phenylpropyl derivatives is due to folding of the side chain onto the phenyl ring. Such folding could be caused by the interaction of the dipole of the side chain with the T electrons of the ring. It would also be promoted by intramolecular hydrophobic bonding. However, the dipolar interaction would appear to be critical in overcoming the small forces which tend to keep the chain extended since propylbenzene, lacking such a dipole, has the expected log P value. This compact form of the phenylpropyl derivative means a smaller apolar surface for solvation and, hence, a lower entropy change in the desolvation process of partitioning. Since the size or kind of polar function has little to do with A T , it seems likely that this function projects away from the ring side-chain complex.
Nmr evidence has been gatheredI40 to show that similar folding occurs in compounds having the following structure.
H.
.CH,OH It has also been suggested141 that such folding results in a lower than expected log P for vitamin K. Folding is included as one of the possible group interaction parameters for a T additivity scheme developed for the cyclohexane-water system.141
(140) B. Baker, M. Kawazu, D. Santi, and T. Schwan, J . Med. Chem., 10, 304 (1967). (141) D. Currie, C. Lough, R. Silver, and H . Holmes, Can. J . Chem.. 44, 1035 (1966).
Obsd log P 2.10 Calcd log P 2 . 1 5
2.94 2.81
1.95 2.20
between RX and CeH6(CH2)8X, constant discrepancy was a observed as shown in Table XIV. The phenylpropyl functions
(138) A. Beckett and A. Moffat, J. Pharm. Pharmacol., 21,144s (1969). (139) D. Goodman, J . Amer. Chem. SOC.,80,3887 (1958).
Certainly folding must be considered whenever a calculated log P must be used. The following two examples indicate how the problem can be treated in a straightforward manner.
diphenhydramine Log P for diphenhydramine = 4.26 0.30 - 0.73 0.50 - 0.95 = 3.38, which would be adequate for most purposes, considering that the observed log P is 3.27.In the above example, 4.26is 2(log Pc~H~). value of 0.30is for a CH2 on The which branching occurs. The value of (-0.73) for the OCH2 moiety is obtained by subtracting 1.50 from 0.77,the value For the for log PE~oE~. -N(CH& unit we have used the value of -0.95 obtained for the solute, C6H6(CH&N(CH3)2. It is assumed that folding of diphenylhydramine occurs in aqueous solution, just as it did in the amine model system used in the calculations. .CH CH,CH,CH,N/ 1 H CI
can be explained if it is postulated that folding will occur in all cases, but if the alkyl chains, RI and Rz, are sufficiently long, they will be placed in such close proximity to the p-allyl group that cancellation of some hydrophobic character due to overlapping occurs. Evidence that hydrophobic overlap can, indeed, lower the partition coefficient can be seen in molecules that are constrained to take an overlapped position. An example would be paracyclophane, whose log P would be expected to be close to twice that of xylene, if the entire hydrophobic area were exposed. CHI-CH,
CHJ-CH, paracyclophane The observed value as shown in Table XVII is even lower than that of xylene itself, and thus it appears that only one-half the potential hydrophobic area is exposed. Of course, we must assume that in all these determinations of P values care was taken to work below cmc. It is conceivable that if a constant solute concentration were employed throughout a homologous series, the cmc would be exceeded with the higher members, giving falsely low log P values for them. While part of the effect noted in the phenoxyacetamide series could have arisen from this cause, it is highly unlikely that all of it can be explained in this fashion, especially since the biological response of the series so closely follows the measured log P values. Although an actual conformational change which brings a polar group on a side chain in close proximity with the n electron cloud on the ring seems the best way to explain these negative Ans(observed - calculated), nevertheless, there are some apparent weaknesses in this hypothesis. First of all, it seems entirely possible that the close approach of the polar group and the ring, which causes the hydrophobic chain to fold on itself, might eliminate a corresponding amount of polar bonding with water, and the loss in hydrophilic bonding might cancel the loss in hydrophobic bonding. Furthermore, the folding must occur in the aqueous phase to cause the unexpectedly low log P, but it is difficult to imagine any induced polar force or charge-transfer condition which would be effective in a medium as polar as water. Finally, once the initial ?r lowering is encountered in several homologous series, no additional effect is seen as the chain length is increased, even though a larger hydrophobic area is presumed to be coming into close contact. This is very apparent in a series of 3-substituted 2-hydro~ynaphthoquinones~~~ the same where - A n is noted whether the polar group and ring are separated by three methylene units or nine. Of course, in a chain longer than three carbon atoms, the entropy gained through hydrophobic overlap might be exactly cancelled by the energy needed to overlap the hydrogen atoms as each C-C bond is rotated in the manner needed for folding the chain. It is to be expected that solutes which can readily form intramolecular hydrogen bonds will adopt this favored con(143) L. Fieser, M. Ettlinger, and G. Fawaz, J . Amer. Chem. SOC.,70, 3228 (1948).
chlorpromazine As another example log P for chlorpromazine can be calculated as 4.15 0.70 0.60 = 5.45,which is in satisfactory agreement with the observed log P = 5.35. The value of 4.15 is log P for phenothiazine. To this is of ~) added n ~ 1 0.70 and 0.60 for ? T ( c H ~ ) ~ N ( c HFor~ .the side chain, n was calculated from a model in which the opportunity for folding was the same as for chlorpromazine.
~(CHZ)~N(CH~)Z PCGH~(CHZ)~N(CH~Z = log
log P c ~ H ~ = 2.73 - 2.13
0.60
The oleyl alcohol-water partition coefficients of a series of phenoxyacetamide derivatives142appear to provide further examples of folding over a benzene ring. In this case, the deviations from additivity in n values appear to be maximized when folding over the ring brings together hydrophobic portions of two para ring substituents. The basic structure investigated can be depicted as CH,=CHCH, OCH When R1 = RP = methyl, log P = 1.53; ethyl, 2.51; n-butyl, 1.80. Folding of the phenoxyacetamide side chain over the benzene ring might be expected to show a constant A n as was indicated in the examples in Table XIV. But after the expected increase in log P in ascending the series from dimethyl to diethyl, a sudden decrease in lipophilic character is noted with the substituent chains of greater length. This observation
(142) T. Irikura, KkugakuZasshi, 8 2 , 3 5 6 (1962).
D. Elkins
figuration during partitioning and that T additivity will certainly be affected. Salicylic acid provides a typical example. log Po-hydroxybenzoic 2.21
noid
- log Pp-hydioxybenaoio
1.58
acid
= AT
& B + H+ HA e H+ + ABH+
aq
0.63
HA
-0-y
c/o
+ HIO e
2HA (HA)n HA.H*O (+ (HA)z*HnO
0%
+ HA2HzO)
The AT for a six-membered H-bonded ring is positive, as expected, because intramolecular H-bonding would reduce the affinity for the aqueous phase. An even further reduction in hydrophobicity is possible when two ortho groups are involved :
has been discussed in section 1I.B. Many of the partition coefficient values reported in Table XVII for solutes which are metal ion complexing agents50,148,149 been measured in order to determine the have equilibrium constant for the reaction of the type
Mn+(w) nHzC(o)
log P (calcd)
log
.-e
Pp-hydroxybenzoic w i d
e M(HC)n(o) + nH+(w)
= 1.58
1.28 log P (obsd) = 2.20 AT = f0.92

=
a e
+ (-0.30)
A(OH para to CO3H)
where M is the metal of valence n,H2Cis the neutral complexing agent (e.g., dithiazone), and (w) and (0)refer to the water and organic phases, respectively. Another type of equilibrium studied by partitioning methods is that between an aldehyde and amine in forming a Schiff base. With ~ a l i c y l a l d e h y d e ~ a ~ ~ of the distribu151 ~ study tion as a function of pH must take into consideration a second equilibrium
An intramolecular H bond of the type (-N-H 0) in a six-membered ring is not expected to be as strong, and the AT is found to be smaller. log Panthianilic 1.21
acid
- log Pp-aminobenmic acid

0.68
= AT = +0.53
V I . Uses of Partition Measurements
CH=NR
CH=NK
A. COUNTERCURRENT DISTRIBUTION
The relationship between the partition coefficient of a particular solute and the number of transfers necessary to properly characterize the distribution curve or to separate it from closely allied impurities is adequately covered in the literat ~ r e . ~ ~ It is~a common~ ~ ~ - ~ ~ ~ number , ~ ~ , practice to make a of separate preliminary runs with both solute and suspected impurity in several solvent systems to attempt to optimize the two solvents used for the final distribution. Following the calculation procedures presented in section V and using the values listed in Table XVII as parent molecules, it may be possible to obtain reliable estimates of partition coefficients of a great number of solutes for many systems in which measurements have not yet been made. This procedure might considerably shorten the time required to find optimal extraction conditions. Furthermore, as more knowledge is gained on the effect of different solvents upon solute conformation (section V.D), better advantage could be taken in enhancing selectivity by providing an environment with precisely the right balance of conformational averages. 2 3 This knowledge might also prove helpful in predicting the possibility of metastable conformational forms which can cause an apparent shift in the partition ratio during fractionation.
The shape of the curves depicting this relationship are seen in Figures 3 and 4. In each figure, section 1 of the curve represents the P value for free aldehyde, section 2 that of the Schiff base, and section 3 that of the phenoxide ion of the Schiff base. From separate evaluation of the dissociation constants of the components of the Schiff base, the log of the formation constant, log Kf, calculated to be 4.75 for the n-butylis salicylidenimineand 4.57 for the methyl analog.
C. RELATIONSHIP TO HLB AND EMULSION SYSTEMS

The HLB (hydrophile-lipophile balance) system, which was has been a very established on a purely empirical potent tool in the hands of emulsion technologists, but it has been felt for some time that even more rapid strides could be made in this field if this system could be directly related to the partition coefficient which is in turn based firmly on thermodynamics. Experimental difficulties have made such a task very difficult,153 but Davies, who studied the kinetics of coalescence in emulsion systems, has proposed an which relates the two in simple fashion (HLB - 7)
=
0.36 In 1/P
B. MEASUREMENT OF EQUILIBRIA
The use of partitioning measurements to determine the equilibrium constants for the reactions
(144) L. Craig, C. Golumbic, H. Mighton, and E. Titus, J . Biol. Chem., 161, 321 (1945). (145) R. Priore and R. Kirdani, Anal. Biochem., 24,360 (1968). (146) L. Craig,J. B i d . Chem., 155, 519 (1944). (147) B. Williamson and L. Craig, ibid., 168,687 (1947).
From this relationship it appears possible to give extrathermodynamic significance to each structural element in deter-
(148) S.Balt and E. Vandalen, Anal. Chim. Acta, 30,434

(149) (150) (151) (152) (153) (154)
(1964). B. Hok, Suensk Kem. Tidskr., 65,182 (1953). R. Green and P. Alexander, Aust.J. Chem., 18,329 (1965). R. Green and E. Measurier, ibid., 19,229 (1966). W. Griffin, J . SOC.Cosmet. Chem., 1, 311 (1949). W. Griffin, ibid., 5 , 249 (1954). J. T. Davies, Proc.Int. Congr. Surface Actiu., 2nd. 1, 476 (1957).
D. MEASUREMENT OF DISSOLUTION AND PARTITIONING RATE OF DRUGS

It is widely accepted that the dissolution rate of any drug given in solid form can have a marked influence upon the amount effectively absorbed. Since drug absorption is also affected by its effective partition coefficient, it is desirable to measure these properties simultaneously. This becomes more important in view of the observation that some surfactants are capable of increasing the rate of solution while simultaneously lowering the rate of partitioning.156 With drugs that are poorly water soluble, the usual measurements of solubility rates require large volumes of water so that the drug concentration is far below the saturation level. Yet this often means that a separate extraction step must be carried out so that a sufficiently high concentration of drug is obtained for accurate analysis. As a model system, hard, nondisintegrating tablets of salicylic acid of uniform surface areas were stirred under standard conditions in aqueous buffer (pH 2) with an upper octanol phase present.lb6 The system can be described as follows.
kl
L ' I PH Figure 3. Formation of n-butylsalicylidenimine and partitioning between toluene and water.
' '
::I:; !I
IO
1 4
ka
A+B+C
A = weight of drug in tablet form, B = weight of drug in aqueous phase, C = weight of drug in octanol phase; then if W. = weight of drug needed to saturate the aqueous phase, and using equal volumes of the two phases, the kinetic equations are -dA/dt
=
kl(W. - B)
dB/dt = ki(We - B) - k2B dC/dt

2 .o
L
knB
In the early stages of dissolution, W , > Band > -dA/dt

=
kiW,
(55)
a
c3 0
Furthermore, for lipophilic drugs, a steady-state concentration of B is quickly attained dB/dt and dC/dt
= =
kl(W, - B)
- kzB
-dA/dt
(56)
I .7
k?B = ki( W, - B)
(57)
6
Figure 4.
8
FH
Formation of methylsalicylidenimine and partitioning between toluene and water.
mining the molecule's ability to function as a wetting agent, detergent, or defoamer.el! l55
The rate of appearance of drug in the lipid phase is easily measured and becomes equal to the dissolution rate in the aqueous phase. If partitioning between aqueous and organic phases is to serve as a model system of how a biologically interesting solute passes through membranes in living tissue, then the rate at which equilibrium is attained might be as important as the equilibrium value itself. For solutes of similar structure, the activation energies for phase transfer are often approximately equal, and therefore the transfer rate constants are proportional to the equilibrium constants, P.9 2 However, an interesting exception was reportedg4when a more rapid rate of partitioning from water to butanol was found for KC1 than for NaCl, even though their P values are approximately equal. The measured difference in activation energy between these salts was 0.8 kcal/mol, which probably was due to
(156) P. J. Niebergall, M. Patil, and E. Sugita, J . Pharm. Sci., 56,943 (1967).
(1 5 5 ) P. Becher, "Emulsions, Theory and Practice," Reinhold, New York, N. Y., 1966, p 233.
Figure 5. Effects of gentle rocking on the interfaces. Partitioning
rate apparatus: Doluisio and Swintosky Y-tube.
SCHULMAN -TYPE CELL
I
A
I I I
K i2
I
C
fore partition studies can be made on various solutes in the presence of trace amounts of surfactants (e.g., phospholipids) at the oil-water interface. Either type of apparatus is capable of providing useful information on the rate of transfer from one aqueous environment through an organic phase (simulating a membrane) to a second aqueous environment. If the solute is placed initially in compartment A at pH 2 and compartment C is at pH 7.4, one has a model for transport across the gastric membrane. The basic importance of partitioning rate studies cannot be seriously questioned, but the interpretation of the results is still subject to some ambiguity. For example, Augustine and Swarbrickl@used a Schulman-type cell to study the effect of lipid polarity on the rate of transport of salicylic acid. As the polarity of the lipid phase was increased (by increasing the mole fraction of isoamyl alcohol in cyclohexane), there was an increase in rate at which salicylic acid left the first aqueous phase. This is the expected result and confirms the work of Khalil and Martinlzl who used a Y-tube apparatus. However, this same increase in polarity also increased k2, the rate at which salicylic acid left the lipid phase for the second aqueous phase. This is unexpected and contrary to Khalil and Martins findings. Augustine and Swarbrick then found that, while keeping the surface to volume ratio constant, they could reverse the order of k2 if they increased the stirring rate in the aqueous compartments. Then k z did decrease with increasing lipid polarity, and the value for kl was essentially unchanged. Other discrepancies between measurements using the Y-tube and the Schulman cells have been noted, and it appears that some of the conditions assumed in the theoretical development that are not being met under all experimental conditions. For instance, it is assumed that the rate-determining step is the actual crossing of the interface boundary. This should be the case if the diffusion layer is of the order of magnitude of 30 p in thicknesg4Some care is required to adjust the stirring rate between that which is so slow that diffusion becomes rate determining and a stirring rate which is so great that nonlaminar flow breaks up the interface.
E. LIQUID ION-EXCHANGE MEDIA AND ION-SELECTIVE ELECTRODES

The application of partition coefficients to the study of liquid ion-selective electrodes has been discussed in section 1I.D. It should be emphasized that the selectivity is dependent upon the nature of the organic solvent and not on the nature of the site species (alkyl acid or amine).
Figure 6. Magnetic stirrers used to study rate of transport across lipoid barrier; A, B, and C have the same meaning as in Figure 5.
differences in the loss of hydration as the ions entered the butanol phase. Two basically different types of apparatus have been designed for partitioning rate studies. Doluisio and Swintosky w employed an inverted Y tube in which the oil phase in the neck was the only connecting link between the separate aqueous phases in the arms (see Figure 5 ) . A gentle rocking motion was applied which gradually expanded and contracted the interfaces. This accelerated solute transfer but normally was insufficient to cause emulsion problems. Earlier, Schulmang devised a two-compartment cell in which the separated aqueous phases were independently stirred from below while the connecting oil phase was stirred from above (see Figure 6). This apparatus has the advantage that the interface area remains constant, and there(157) J. Doluisio and J. Swintosky, J . Pharm. Sci., 53,597 (1964).
F. MEASUREMENT OF HYDROPHOBIC BONDING ABILITY. STRUCTUREACTIVITY PARAMETERS

In the introduction it was pointed out that in the past decade far more partition coefficients have been determined in connection with biological structure-activity relationship studies than for all other purposes combined. A large number of these 159 and the usefulness studies have already been referred of the octanol-water parameter to predict the binding of solutes to serum albumin and to purified enzymes has been convincingly established.
(158) M. Augustine and J. Swarbrick, ibid., 59,3 14 (1970). (159) W. Scholtan, K. Schlossman, and H. Rosenkranz, A?.Forsch., 18, 767 (1968).
Table X V
Improved T Values
Phenox yace tic
Firmtion
acids
Function
3-Me
Phenylacetic acids
0.54
Function
Benzoic acids
3-F 2-c1 2-Br

4-Rr
4-1
2-Me
0.22 0.76 0.84 1.19 1.43 0.84

0.60
3-CF3 3-CN 3-OCH3 3-COzH 3-SOzCHa
1.21 -0.23 0.09 -0.27 -1.35
4-C1 3-OCHCOzH 3-CN 4-NHz 4-OH 4-OCHzCOzH
4-Me 2-Et 2-NOS

a
1.39
-0.04
0.78 -0.76 Phenols 0.22 -1.44 Anilines -0.86 Nitrobenzenes -0.31
Differing by more than 0.05 from those listed in ref 10.
Evidence is rapidly accumulating which supports the postulate that simple, nonspecific bonding of solutes is capable not only of markedly affecting enzyme action through allosteric effects, but that it often produces biologically important modifications of membrane function by a similar mechanism. For example, it has been shown that the action of alkanols in the protection of red cells against hypotonic hemolysis is a linear function of their hydrophobic character as measured by partitioning experimentsI6O and, furthermore, that the concentration which affords hemolytic protection is very nearly the same as that which causes anesthesia.161 The partition coefficient of alcohols between red cell ghosts and water has been measured, and it was found that in going from water to membrane, the free energy of transfer per methylene group was the same as that between water and octanol, namely, - 690 cal/mol. The usefulness of a bonding parameter based on partition values from a single reference system can be greatly extended if not every value required in every structure-activity study need be measured. The principles of additivity for the octanol-water system were covered in section V, and examples of how values in Table XVII can be systematically applied in this fashion are given in the following section.
The solute name appears in the right-hand column of Table XVII, and the reference from which the data were obtained appears in column 4. Column 6 lists the measured log P for the solute in the solvent system which appears in column 3. This value has been corrected for ionization, if any, and dimerization if measurements were reported over a sufficiently wide concentration range. The values are footnoted (column 5 ) as required. Column 7 lists the calculated log P for that solute in the octanol-water system. The regression equations used for this calculation appear in Table VI11 together with the values for the standard deviation (s), the correlation coefficient (r), and the number of data points (n) which were available to establish the relationship. While the standard deviations indicate that some of these regression values are not sufficiently reliable for some purposes, nevertheless, they are useful in providing the only common scale of lipophilicity since only 2 0 x of the values in the entire table are from a single system. Space limitations and the absence of small letters and italics in computer printing precluded the use of the Chemical Abstracts system of nomenclature. For convenience in computer alphabetizing, the following rules were followed.
1. Aliphatic chains-branching: I = iso, S = secondary, and T = tertiary, as usual. Normal isomers are assumed if not specified; Le., BUTYRIC ACID = n-butanoic acid. N = nitrogen; e.g., N-methylaniline. 2. Aliphatic chains-location from primary functional group is designated by Greek letter: A = a, B = p, G = y , D = 6, E = E, and W = W ; e.g., A-BROMOPROPIONIC ACID.
V I / . The Use of Table X V l l

The amount of partitioning data uncovered in the present study was great enough to warrant its storage, manipulation, and retrieval by computer. It will be noted that some of the log Pootanal values listed in Table XVII differ slightly from those published earlier from this laboratory. Generally, the differences resulted from the use of improved analytical techniques and the values in Table XVII should be considered more reliable. The significant changes in T constants from those contained in ref 10 appear in Table XV. In Table XVII the data have been sorted in their most useful form; namely, the solutes are sorted first by empirical formula, then alphabetically by name, and finally by solvent syssystem.
(160) H. Schneider, Biochim. BiophJ.8. Acta, 163, 451 (1968). (161) P. Seeman, S . Roth, and H . Schneider, ibid., 225, 171 (1971). (162) As stored in the computer, each solute has also been given a unique Wiswesser line notation (The Wiswesser Line-Formula Chemical Notation, E. G. Smith, Ed., McGraw-Hill, New York, N. Y., 1968). A comparison of T values by functional groups IS greatly facilitated by referring to a printout sorted by a permuted alphabetic listing by WLN notation.
3. Position on benzene rings

(a) if only two functional groups or substituents: 0 = ortho, M = meta, and P = para, and the letter precedes the name; e.g., 0-NITROPHENOL, (b) if three or more substituents, numbering is from primary functional group ; e.g., DIMETHYLPHENOL.
4. In all other ring systems, a numbering system is used regardless of the number of substituents; e.g., 3-AMINOPYRIDINE, 2-NAPHTHOL.
5 . For sorting and retrieval purposes, many trivial names
were relegated t o a secondary position; e.g.,

ECHOL/.
M-DIHY-
DROXYBENZENE/RESORCINOL/;0-DIHYDROXYBENZENE/CAT-
552 Chemical Reviews, 1971, Vol. 71,
No. 6
6. In the empirical formula, the subscript 1 is expressed and not assumed. It is unlikely that, for the foreseeable future, there will be measured log P values for more than a small fraction of the interesting molecules which might be needed in structureactivity work. One of the aims of this present article is to make it possible to calculate, with a reasonable degree of confidence, the log P values in one common system (octanol- water) for a wide variety of molecules for which values have not, or perhaps cannot, be determined. The present section will explain how the calculation procedures given in section V can be combined with the regression equations of Table VI11 and the data in Table XVII to yield calculated values of the highest possible confidence level. It was evident in section V that there are often several routes by which one can calculate a Pactanol value, depending upon the choice of parent molecule and how substructures are pieced together. If the computed values by all the routes agree within k O . 1 log unit and also agree with any for log Pootanol that solute appearing in Table XVII as calculated from another solvent system, then one can accept an average value with some confidence. If there are some widely divergent values, however, then one must choose the route which has the greatest likelihood of yielding an accurate value. In order to help make such a choice, we have assigned uncertainty units (uu) to each type of calculation step so that the route with the lowest sum is the one which can be used with greatest confidence. Although these u units have been assigned by considering the average deviation in log P values of solutes with the required structural differences, and even though they can be directly added to the standard deviations of the regression equation values (see Table VIII), they are not to be considered as standard deviations in the strict sense. They are listed in Table XVI. The standard deviations of the observed log Pootanol values are used if given in the reference; otherwise, an arbitrary uu of 0.05 is taken. The following examples illustrate this procedure [the superscripts mean that the values were obtained from (a) Table VIII, standard deviation; (b) Table XVI; (c) Table XVII].
(A) Menthol : no log Poctmeasured (1) Regression from oil-water system log Poot= (3.25 and 3 3 .7)
=
Table X V I
Uncertainty Units
Calculation step o r group aper step or group Uncertainty units
(uu)
Comments and exceptions
1. -CHz-
0.50
0.02 (a) a lower if between two very polar groups, e . g . , malonic acid (b) T lower if folding interaction possible (section V.D)
0.02 (a) Sign of a changes if
2. Branching (a) in C chain

(b) of functional
-0.20
steric blocking of polar group possible group

(c) ring closure
3. Double bond -0.20 -0.09 -0.30 0.05
0.02
0.03 0.05 (a) See unusual case of
4. Folding
5. Intramolecular
-0.60
phenoxyacetamides (section V.D) H-bonding

6. Equivalence of aliphatic OH and
0.65
0.00
0.10
NHz
7. Aliphatic groups
0.05 0.03
(a) -COOH (b) -OH (c) -NHz (d) -C=O (e) -CN
(f) -0(g) -CONHz
-0.65 -1.16
-1.16
-1.21 -0.84 -0.98 -1.71
(h) -F (i) -C1

(j) -Br (k) -1
-0.17
0.39 0.60 1 .OO
0.03 0.03 0.03 0.04 0.05 0.05 0.03 0.04
0.04
0.05
For aromatic substituents, use a values and standard deviations (as uu) appearing in T. Fujita, et al., J. Am. Cheni. SOC.,86, 5175 (1964).
av 3.31
uu
0.02b
+ 0.08b+ 0.02b= 0.12
uu
= 0.28a
Route 2 should be chosen for several reasons. It has the lowest uu value. The electronic effect on a of the difference between an aliphatic and aromatic OH group is precisely allowed for. Adding the isopropyl group adjacent to the OH in route 3 may involve a steric blocking of its hydrophilic character.
(B) n-Propylamine: no log Paot measured
log Poet = 3.30
(3)
+ (-0.23) = 3.07 uu = 0.02b+ 0.04b= 0.06 CsH50H + (CH3)zCH- + -CH3

1.23 (1.50 - 0.20) 0.52
(1) Equivalence of OH and N H z log Poet (propanol)

uu
= =
0.34
0.07b
(2) (CH3CHNHzCH3)- (branch) log Po,$= -0.03

uu
=
- (-0.20)b
0.17
log Pact= 1.23
+ 1.30b + 0.50b = 3.03
0.02b
+ 0.05b= 0.07
(3) nPropylamine log Poct(regression from ether-water)

=
(4) Regression from i-BuOH-water 0.37

( 5 ) Regression from CHC13-water (av 2)
-0.39
0.14'
0.08 0.27*
uu
= 0.27'
(4) n-Butylamine - methyl log Post = 0.81'
- 0.50b = 0.31
Clearly the value by route 5 is eliminated from consideration and a value in the range of -0.36 to -0.40 is preferred.
0
uu
= 0.02b
+ 0.02b = 0.04
( F ) Atropine c +Lc , H = ! -Ho
Since route 4 has the lowest uu and is reinforced by (1) and (3), it is preferred over (2). (C) Lactic acid: log Po,+ = -0.62' (1) Hydroxyacetic acid log Po,t = -1.11'
methyl branch = CH3CHOHCOzH
[ C G = H ] -
[OH] -I-[C,HjCH2COLH]
+ 0.50b + (-0.20)b = -0.81 uu = 0.05' + 0.02b + 0.05b = 0.12

log Pact (av of 5 ) = -0.80
[CH,OHl
+ [branch]
log Poct = -0.28'
- (-1.16)b
+ 1.30' +
(-0.66)c
(2) Regression from ether-water
uu
0.27'
+ 0.05b+ 0.02' + 0.02'

1.30' (-0.66)c
+ -0.20b = 1.32 + 0.02' = 0.38 + + (-0.20)b = 1.81 + 0.02' = 0.26
uu
0.19'
(2) As (1) but log P tropine regr. from i-BuOH-water log P , - B ~ o H 0.21' - (-1.16)b =
(3) (CH3)zC(OH)C0,H - methyl - branch = lactic acid log Pact = -0.36'
- 0.50b - (-0.20)b
= -0.68
uu
0.05'
+ 0.02b + 0.02b = 0.09
uu
0.15'
+ 0.05b + 0.02' + 0.02'
The measured log Poctagrees quite well with that arrived at by route 3. The values arrived at by routes 1 and 2 should not be totally disregarded, however, because the presence of an appreciable amount of polylactic acid impurity in the sample measured by Collander could be responsible for an observed value which was 0.1 to 0.2 unit too high.
The measured log Pact for atropine is 1.81 which is in agreement with route 2. The uncertainty of route 1 is not that much worse than (2), but the measured value for tropine in etherwater appears very doubtful.
( G ) p-N-Methylaminobenzoic acid, N,N-dimethylaminoethyl ester

c H , HO HC - H ~ - C , HNC ,I
,)?
(D) Acetonylacetone: log Pmt not measured

log P uu (1) Regression from ether-water -0.19 0 . 19' (2) Log Poet(acetone)c X 2 -0.48 0.10 (3) 2-Butanone acetone - methyl = CHCOCHCHzCOCH3
log Pact = 0.29'
+ (-0.24)' - 0.50b = -0.45 uu = 0.02' + 0.05' + 0.02b = 0.09 + CH3COzH =

CH3COCHzCHzCOzH
+ (CBH,&OOCH~-)+ (-CHzN(CHa)z) log P = (0.50b - 1.23*) + 2.12' + 0.27' = (1.66) uu = O.Olb + 0.02b + 0.02b + 0.05d = (0.10)
(1) CHaNHlog P ~ c o r r ) l= a2.03 a
uu = 0.18
(2) Regression from oil-water log Pact = 2.01'
The choice clearly favors the range -0.45 to -0.48.
(E) Levulinic acid: log Pact not measured

CHaCOCH3
uu
= 0.29"
=
log Pock = -0.24'
uu
0.05'
2-Butanone
+ aliphatic -COzH
+ (-0.17)' = -0.41 + 0.02' = 0.07
(3) Log Poet(measured)
1.95'
log Poet = 0.29'
+ (-0.65)b = -0.36 uu = 0.02' + 0.03b = 0.05

logP uu 0.19'
In these first examples, the amount of interaction between the component parts used in the calculations was either small or it could be taken into consideration (as in G ) .In the following example this is not the case, and it can be seen that it is possible to use the proposed method of calculation to support an erroneous measured value.
T N H ~ = -1.23 uses benzene as the "parent." Correcting for electronic effects (ref 10) using u (-COCHa) = 0.39, we correct w by 0.37 and add to the uu by 0.08.
Regression from ether-water (av 3)
-0.40
(163)
A. Leo, C. Hansch, and D Elkins .
II
Log Poctregression from ether-water Log P,,t regression from CHC13-water Log P,,t regression from oil-water Log P,,t regression from i-BuOH-water
logP -0.06'
uu 0,27'
0.53' 0.27' -0.12' 0.28' 0.15' 0.28' 0.21' 0.15'
The value of 0.21 should be favored because it has the lowest uu value, but one could attempt to verify it by calculation.
0
Log P
2.13' (-0.21)' (-0.30)b (0.27' - l.O)b
+ (-0.20)b +
(-0.18)b
=
0.53
uu
0.02'
+ 0.02' + 0.03b + 0.05' + 0.04h + 0.02b + 0.04h = 0.22
Without any allowance for an interaction between the amide and amine nitrogen atoms, route 5 would support route 2. With such a variety of values to choose from and no clear preference indicated by uu values, the only safe course is to measure the P value directly. In this case log Pootturned out to be 0.23 and the route 4 was vindicated.
Acknowledgment. This work was supported under Research Grant CA 11110 and Contract No. 70-4115, both from the National Institutes of Health.
V I / / . Glossary of Terms
Aa
B BH+ C
anionic form of acidic solute degree of ionization neutral form of basic solute protonated form of basic solute molar concentration
critical micelle concentration (molar) steric parameter as defined by Taft average energy level of j t h group free energy enthalpy neutral form of acidic solute dihydric complexing agent hydrophile-lipophile balance dissociation constant of single molecules into ions in aqueous phase association constant of single into double molecules in lipoid phase; equals ~ / K D dissociation constant of double into single molecules in lipoid phase association constant between hydrogen bond donor and acceptor association constant for formation of complex or imine Boltzman constant milliliters of lipoid extracting phase metal ion carrying charge of n+ (in counter-current distribution) position of peak (in partition calculation) concentration of un-ionized solute in water at first concentration level (in molil.) (in counter-current distribution) total number of tubes (in partition calculation) concentration of un-ionized solute at second concentration level (in mol/l.) (in regression equations) number of data points treated organic (or oil) phase partition coefficient ; nonpolar/polar phase ; refers to concentration of neutral solute unless specified (only exception is in eq 19 and 20 where P refers to pressure) apparent partition coefficient (total solute measured, regardless of form) thermodynamic partition coefficient = ratio of mole fractions in nonpolar/polar phases. negative logarithm of acid ionization constant hydrophobic substituent constant; T X = log PX log P H gas constant (in regression equations) correlation coefficient (in counter-current distribution) specific tube number standard deviation entropy electronic parameter as defined by Hammett (in counter-current distribution) fraction of total solute absolute temperature chemical potential (per mole) molar volume of solvent ml of aqueous solution being extracted water phase mole fraction particle partition function (quantum mechanics) state function (quantum mechanics)
Table XVII. SORTED

NO. SOLVENT OILS NITROBENZENE CCL4
B Y EMPIRICAL FORMULAt THEN NAME, THEN SOLVENT NUMBER, THEN REFERENCE. MEASURED WLOGP OCT" FOLLOWED BY "-*: OTHERS CALC FROM S P E C I F I E D E 9 I N TABLE V I 1 1
REF FOOT NOTE LOGP SOLV 0.bC -5.04 1.35 1.89 1.80 -1.82 -1.74 -1.74 -5.36 -1.55 -1.76 -1.74 -1.19 -1.74 1.29 -0.46 -1.74 -3.15 0.23 0.54 -0.70 -3.74 -5.00 -4.59 -3.60 2.12 2.59 2.29 -1.66 1.93 2.77 1.87 1.59 2.62 0.88 0.55 1.15 1.09 2.04 1.16 -1.04 -0.64 -2.92 0.84 0.86 -0.16 -0.44 -1.18 -1.36 -0.94 -1.19 -2.78 -3.34 -2.30 -0.48 -0.41 -2.30 -0.85 -0.85 -0.60 -1.11 -1.00 -0.52 0.30 0.73 0.95 0.89 -1.96 -1.35 -1.09 -1.40 -0.85 -2.35 -2.28 -2.58 -2.34 -1.35 -1.65 -0.66 -0.87 0.20 2.42 2.66 -0.75 2.08 1.70 1.97 1.86 0.38 0.26 -0.67 -0.66 -0.35 -0.57 -1.38 -0.45 -0.45 -0.96 -2.35 -0.30 LOGP OCT EMPIRICAL FORMULA B AR1 BR1K 1 BRZ BR2 BR2 CLlCSl CLlKl CLlKl CLlKl CLlLIl CLlNAl CLlNAl CLlNAl CLlRBl cL2 CL2HGl 0201 0201 HE1 Il8Rl IlCLl l l K l IlLIl IlNAl IlRBl I 2 I 2 I2 I2 I2 I 2 I2 I 2 12 KR1 N2 04OSl 04051 RD1 XE1 HlCLl HlFl HlFl H1N3 HlN3 H1N3 NAME ARGON POTASSIUM BROMIDE BROMINE BROMINE BROMI N E CESIUM CHLORIDE POTASSIUM CHLORIDE POTASSIUM CHLORIDE POTASSIUM CHLORIDE L I T H I U M CHLORIDE SODIUM CHLORIDE SODIUM CHLORIDE SODIUM CHLORIDE RUBIDIUM CHLORIDE CHLORINE MERCURIC CHLORIDE DEUTERIUM OXIDE OEUTERIUfl OXIDE HELIUM I O D I N E MONOBROMIOE I O D I N E MONOCHLORIOE POTASS IUM I O D I D E LITHIUM IODIDE SODIUM I D O I O E RUBIDIUM I O D I D E IOOINE IODINE IODINE IODINE IODINE IODINE IODINE IODINE IODINE KRYPTON NITROGEN OSMIUM TETROXIDE OSMIUM TETROXIDE RACON XENON HYDROGEN CHLORIDE HYDROFLUORIC ACID HY DROFLUOR I C A C I 0 HYOROGEN AZIDE HYDROGEN AZIDE HYDROGEN AZIOE WATER HYDROGEN PEROXIDE HYDROGEN PEROX I O HYDROGEN PEROXIDE HYDROGEN PEROX I O E HYDROGEN PEROXIDE HYOROGEN PEROXIDE HYDROGEN PEROXIDE HYDROGEN PEROXIDE HY DROG EN P EROY I O E HYOROGEN PEROXIDE HYCROGEN PEROXIDE HYDROGEN PEROXIDE HYDROGEN PEROXIOE HYOROGEN PEROXIDE ORTHOPHOSPHATE ANION ORTHOPPOSPHATE ANION PYROPHOSPHATE ANION PYROPHOSPHATE ANION HYDROGEN SULFIDE HYDROGEN SULFIDE AMMONIA AMHONI A AMMONIA AMMONIA AMMONIA AYMOhIA HYDROXYL AMINE HYDROXY LAM I NE HY DRAZ I N HYORAZ I N HY OR AZ I N E AMMONI UM HY DROXI DE AMMON 1UM HYOROXI DE CYANOGEN CHLORIDE CHLOROPICRIN CARBON TETRACHLORIDE I O D I N E CYANIDE CARBON OISULFIOE CARBON DISULFIDE CHLOROFO RH
CHLOROFORM
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62
csz
164 92 165 165

166 91 91
22 46
0.94
t 3
64 65 66 67 68 69 70 71 72 73 14 75 76 77 78 79 80 81 e2 e3 e4 5 e6 87 88 89 90 91 92 93 $4 55 96 57 98 99 100
BROMOFORM N-BUTANOL N-BUTANOL N-BUTANOL NITROBENZENE N-BUTANOL N-BUTANOL N-BUTANOL SEC-BUTANOL N-BUTANOL CCL4 OILS DIETHYL ETCER OILS OILS CCL4 CCL4 NITROBENZENE NITROBENZENE NITROBENZENE NITROBENZENE CHCL3 BENZENE NITROBENZENE PRIM. PENTANOLS CCL4 CS2 OOCECANE HEXAOECANE BROMOFORM OILS OILS CCL4 CCL4 OILS OILS OILS DIETHYL ETHER CHCL3 DIETHYL ETHER DIETHYL ETCER CHCL3 SEC-BUTANOL DIETHYL ETHER DIETHYL ETHER DIETHYL ETFER DIETHYL ETHER CHCL3 CHCL3 BENZENE I-BUTANOL I-BUTANOL NITROBENZENE PRIM. PENTANOLS PRIM. PENTANOLS ETHYL ACETATE I-PENT. ACETATE N-BUTANOL HEXANOL N-BUTANOL HEXANOL DIETHYL ETHER CHCL3 DIETHYL ETHER CHCL3 SEC-BUTANOL TOLUENE PRIM. PENTANOLS CCL4 DIETHYL ETPER CHCL3 OIETHVL ETCER CHCL3 BENZENE I-BUTANOL PRIM. PENTANOLS OILS OILS OILS C C L ~ OILS OILS OCTANOL OILS DIETHYL ETHER DIETHYL ETI-ER CHCL3 CHCL3 BENZENE BENZENE CCL4 ETHYL BROMIDE BROMOETHANE OIETHYL ETHER OILS P R I M . PENTANOLS
94 92 91 91 94 94 91 167 168 2 2 164 169 169 92 92 92 92 165 170 170 47

166
46 46 46 46 46 46 46 46 46 51 46
-3.03 -2.92 -2.94 -2.66 -2.96 -2.94 -2.92 0.06 -1.42 -1.64 0.66 B A A B
22 46
46
46 46
166 165 165

166
164 164 171 172 164 164 173 174 174 175 174 114 84 176 177 178 174 179 174 179 179 178 179 177 180 178 178 181 181 181 181 174 174 174 174 84 68 182 7 174 174 174 174 183 184 184 173 173 173 185 173 82 186 173 187 174 187 174 187 i8n 187 in7 187 3 2 in9
22 22 22 22 12 26
1.16 0.92
2.05 1.37 0.25 -0.44 -1.43 0.86
B B B B A A
A
A
A
0.88
1.07 -1.15 -0.92 -1.08 -0.70 -0.92 -1.29 -1.82 -C.89 -1.19
-1.09
A
A A
H2Ol
H202 ~ 2 0 2 ~ 2 0 2 H202 ~ 2 0 2 ti202 ti202 ~ 2 0 2 ~ 2 0 2 H202 H202 H202 H2OZ HZO2 H204P1 H204P1 H207PL H207P2
HZS 1
26 12 26 26
A A A A
.
26
-1.03 -1.38 -1.37 -0.70 -1.33
10 18 10 18
19
0.96 1.44 -0.90 -1.37 -2.04 -0.35 -1.49 -1.56 -1.87 -1.13 -1.23 -1.37 -0.60 0.64 2.44 2.64 2.16 1.84 1.97 1.98 0.45 0.35 0.62 1.07 0.81
A N B B
B B A A B B 8
B B B B 8
'
=
B
A
A A A A
12
-0.72 -0.91 -0.68
A A
H2Sl H3N1 H3N1 H3N1 H3N1 H3N1 H3N1 H3N101 H3N101 H4N2 H4N2 H4N2 HSNlOl H5N101 ClCLlNl ClCL3N102 ClCL4 ClIlNl ClS2 c1s2 ClHlCL3 ClHlCL3 ClHlNl ClHlNl ClHlNl ClHlNl ClHlNl ClHlNl ClHlNl ClHlNl ClHlNl ClH2N2 ClH2N2 ClH2N2
HYDROCYANIC HYOROCYANIC HYDROCYANIC HYDROCYANIC HYDROCYANIC HYDROCYANIC HYDROCYANIC HYDROCYANIC HYDROCYANIC CYANAnIOE CY ANAM I O E CYANAMIDE
ACID
ACID ACID ACID ACID ACIO ACID ACID ACID
A. Leo, C. Hansch, and D Elkins .
NO. 101 102 103 104 105 106 1C7 108 109
SOLVENT
REF FOOT NOTE 189 189 189 188 5 190 12 12 12
LOGP SOLV -0.19 -0.71 -0.23 -0.96 -0.54 -0.52 -0.40 -0.45 -0.40 -0.43 -2.50 -2.12 -1.84 -2.95 -2.70 -2.57
LOGP OCT -0.26 -0.28 -0.27
EMPIRICAL FORMULA ClH2N2 ClH2N2 ClHZNZ ClH2Ol ClH202 ClH202 ClHZOZ ClHZD2 ClH202 ClHZO2 ClHZOZ ClH202 ClHZOZ ClH202 ClH202 ClHZOZ ClHZOZ ClH202 ClHZOZ ClH202 ClH202 ClH202 ClH202 ClHZOZ ClH202 ClHZO2 ClH202 ClH202 ClHZOZ ClHZOZ ClH202 ClHZOZ ClH202 ClH202 ClH202 ClH3I1 ClH311 ClH3NlOl ClH3NlO1 ClH3N102 ClH3N102 ClH3N102 ClH3N102 ClH4N2O 1 C 1H4NZO 1 ClH4NZO 1 ClH4N201 ClH4NZOl ClH4NZSl ClH4NZS1 ClH4NZS1 ClH4NZS1 ClH4NZS1 ClH4NZS1 ClH401 ClH401 ClH401 ClH401 ClH401 ClH401 ClH401 ClH401 ClH401 ClH401 ClH401 ClH5N1 ClH5N1 ClHSNl ClH5N1 ClH5N1 ClH5N1 ClH5N1 ClH5N1 ClH5Nl ClH5N1 C2H 1BR2 N3 CZH 1 0 RZ N3 CZHlCL302 CZHlCL302 CZHlCL302 C2HlCL302 C2HlCL302 CZHlCL302 CZHlCL302 CZHlCL302 C2H 1CL3 0 2 C2HlCL302 CZHlCL302 CZHZCLZ02 CZHZCLZ02 CZHZCLZOZ CZHZCL202 CZHZCL.202 CZH2CLZ02 CZHZCLZOZ CZH2CL202 CZHZCLZOZ CZHZCL202 CZHZCL3N101 CZHZCL3N101
NAME CY ANAH I DE CYANAMIDE CY ANAM I OE FORMALDEHYDE FORMIC ACID FORMIC ACIO FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC A C I O FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORHIC ACID FORMIC ACID FORMIC ACID F O W I C ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC ACID FORMIC A C I O FORMIC ACID FORMIC ACID METHYL IOOIOE METHYL IODIDE FORMAM I DE FORHAHIDE NITROMETHANE N I TROMETHAYE NITROWETHAYE NITROMETHANE UREA
bREA
ETHYL ACETATE 01-I-PR. ETHER ME- I -8U 1 K ETONE . DIETHYL ETHER OCTANOL OIETHYL ETHER DIETHYL ETHER OI'ETHYL ETHER 0 I ETHYL ETHER 110 DIETHYL ETHER 111 CHCL3 1 1 2 CHCL3 113 OILS 1 1 4 BENZENE 115 BENZENE 1 1 6 BENZENE 1 1 7 N-BUTANOL 1 1 8 SEC-BUTANOL 1 1 9 XYLENE 1 2 0 TOLUENE 1 2 1 TOLUENE 1 2 2 NITROBENZENE 1 2 3 PRIM. PENTANOLS 1 2 4 ETHYL ACETATE 125 CCL4 ETHER 1 2 6 01-I-PR. 1 2 7 2-BUTANONE 1 2 8 ME- I-BUT.% ETONE 1 2 9 ME- I-8UT.KETONE 1 3 0 OLEYL ALCOHOL 1 3 1 0-NITROTOLUENE 1 3 2 S-P ENTANOL S 1 3 3 S-PENTANOLS 1 3 4 CSZ 1 3 5 PARAFFINS 1 3 6 OCTANOL 1 3 7 0 1 ETHYL ETHER 1 3 8 0 1 ETHYL ETPER 139 OILS 1 4 0 OCTANOL 1 4 1 OCTANOL 1 4 2 CYCLOHEXANE 143 OILS 1 4 4 DIETHYL ETHER 1 4 5 OIETHYL ETHER 1 4 6 DIETHYL ETHER 1 4 7 CHCL3 148 OILS 1 4 9 OCTANOL 1 5 0 0 1 ETHYL ETPER 1 5 1 OIETHYL ETHER 1 5 2 DIETHYL ETkER 1 5 3 CHCL3 154 OILS 1 5 5 OCTANOL 1 5 6 OCTANOL 1 5 7 DIETHYL ETHER 158 DIETHYL ETHER 1 5 9 CYCLOHEXANE 1 6 0 CHCL3 1c1 OILS 162 OILS 163 OILS 1.54 O I L S 165 NITROBENZENE 1 6 6 OCTANOL 1 6 7 DIETHYL ETPER 168 CHCL3 1 6 9 CHCL3 170 CHCL3 1 7 1 BENZENE 1 7 2 I-BUTANOL 1 7 3 XYLENE 1 7 4 TOLUENE 1 7 5 PRIM. PENTANOLS 1 7 6 OCTANOL 1 7 7 OCTANOL 1 7 8 DIETHYL Ell-ER 1 7 9 DIETHYL ETHER 1 8 0 DIETHYL ETHER 1 8 1 01 ETHYL ETPER 1 8 2 CHCL 3 1 8 3 BENZENE 1 8 4 TOLUENE i e 5 NITROBENZENE 1 8 6 PRIM. PENTANOLS 1 8 7 BROMOETHANE 1 8 8 1000HETHANE 1 8 9 DIETHYL ETl-ER 1 9 0 01 ETHYL ETHER 1 9 1 DIETHYL EThER 1 9 2 CHCL3 193 OILS 1 9 4 BENZENE 155 TOLUENE 1 9 6 NITROBENZENE 1 9 7 CCL4 158 1OOOMETHANE 1 9 9 OCTANOL 200 DIETHYL ETHER
0.00
-0.54 -0.34 -0.31
=
A A
191
192 46 36 45 36 193 45 44 193 190 190 193 193 41 48 190 194 45 190 190 195 196 5 48 190 195 193 197 5
-0.28
-0.23 -0.25 -1.03 -0.69 -0.44 -1.55 -1.28 -1.15 -0.62 -0.47 -0.97
A
A
A
A A A A A A A A
12
-0.08
0.03 -2.38 -2.58 -2.66 -1.67 -0.26
-0.73
-0.51 -0.73 -0.30 -0.42 0.39
-0.23
26 -3.12 -0.84 0.12 -0.34
-0.37
-0.40 -0.35 -0.22 -0.56 1.69 1.80 -1.67 -1.61 -0.33
-0.38
12 -0.92 -1.81 0.07
-0.22
-3.23 -2.90 1.69 1.92 -2 85 -3.12
=
A 0 A
3 3 2
186 5 141 173
-0.33 00 .8
-0.93
0.08
0.17 -2.79 -2.96 -2.76 -2.97 -2.26 -1.14 -1.80 -1.70 -0.95 -2.38 -1.43 -0.66 -0.82 -0.63 -1.00 -0.66 -0.55 -0.63 -0.73 -0.65 -0.46 -0.57 -0.60 -0.71 -1.00 -1.15 0.37 -0.52 -0.43 -0.35 -0.98 2.44 2.24 1.49 1.18 1.54 1.60 0.61 0.10 0.72 0.91 1.96 1.20 1.39 1.27 0.41 0.94 0.00 0.79 -0.14 1.04 1.06
= =
0 A A A N A
-0.32
-3.33
-3.52 -3.30 -3.85 -3.82 -1.14 -2.20 -2.10 -2.14 -3.10 -2.92 -0.66 -0.82 -0.85 -1.29 -1.84 -1.36 -1.96 -2.01 -2.11 -2.02 -1.60 -0.57 -1.64 -0.56 -0.90 -1.09 -1.34 0.00 -1.00 -1.40 -0.45 2.44 2.24 1.57 1.21 1.63 1.78 -0.69 -1.30 -0.98 0.04 1.79 -0.26 -1.06 1.24 1.46 1.31 -0.89 -0.30 -1.40 -1.42 -0.10 -2.31 -1.15 1.04 1.08
3
112 198 112
2
9 3
112 198 112 2 186 5
12
A A A N A
= =
A A
N
3
174 199 174 173 101
A
A A A
200
201 202 5
=
8 8 8 0 B
0 0
203
68 204 205 184 46 205 182 206 206
12
UREA UREA UREA THIOUREA THIOU&EA TH I OUR E A Trl IOUREA Tn IOll3EA THIOJREA METHAhOL METHANOL METHAhOL METHAhOL METrlAhOL METrlANOL METHA40L PlETHAhOL METHAVOL METHANOL METHANOL METHYLAMINE METHYLAHIhE METHYL AMINE METnYLAHINE METHYLAYINE METHYL AH I N HETHYLAYINE METHYL A M I h E METHYL AM INE METHYLAMINE
= =
A A A A A
A
1~2~3-TRIAZOLE~4~5-DIBROMO
l r 21 4-TR I AZOL E t 3 r 5-0 I BROMO TRICHLOROACETIC AC IO TRICHLOROACETIC ACID TRICHLOROACETIC ACID T R ICHLOROACETIC AC I J TRICHLOROACETIC ACIS TRICHLOROACETIC AC IO TRICHLOROACETIC ACID TRICHLOROACETIC ACID TRICHLOROACETIC ACID TRICHLOROACETIC ACID TRICHLOROACETIC ACID OICHLOROACETIC ACID OICHL3ROACETIC ACID 0 1 CHL IROACET I C A C I 9 OICHL3ROACETIC A C I O OICHLOROACETIC ACID OICHLOROACETIC A C I D OICHL5ROACETIC ACID 01 CHLO ROACET I C AC I O 01 CHLORO ACE T I C AC ID OICHLOROACETIC ACID TRICHLOROACETAHIDE T R ICHLOROACETAMIOE
3 207 113 46 43
2 08
43 43 43 43 41 192 113 46 113 209 208 43 43 43 41 56 113
A A A
A
A
A
0.33 A
A
12
=
A

LOGP OCT 0.81 0.12 EMPIRICAL FORMULA NAME
NO. 20 1 202 203 204 2C5 206 2C7 208 209 2 10 211 212 213 2 14 215 2 16 211 218 2 19 2 20 221 222 223 2 24 225 226 227 228 2 29 230 231 232 2 33 2 34 235 236 231 238 2 39 2 40 241 242 243 244 245 246 241 248 249 2 50 251 252 253 254 255 256 251 258 259 260 2c 1 2c2 2.5 3 264 265 266 26 1 268 269 210 2 11 212 273 214 215 216 271 218 2 19 2 80 281 282 283 284 285 286 281 288 289 290 291 292 293 294 295 296 291 298 299 300
SOLVENT
REF FOOT NOTE 113 2 10 211 212
LOGP SOLV
CHCL3 OCTANOL DIETHYL ETbER DIETHYL ETFER DIETHYL EThER DIETHYL ETbER OIETHYL ETPER DIETHYL ETFER N-BUTANOL PRIM. PENTANOLS ETHYL ACETATE HEXANOL HE- I-BUT .KETONE S-PENTANOLS OCTANOL OIETHYL ETHER CHCL3 OILS BENZENE XYLENE TOLUENE OILS DIETHYL ETHER 01 ETHYL ETHER DIETHYL E T P E R DIETHYL ETHER 01 ETHYL ETHER CHCL3 CHCL3 CHCL3 OILS BENZENE BENZENE TOLUENE TOLUENE TOLUENE TOLUENE NITROBENZENE NITROBENZENE CCL4 1000METHANE DIETHYL ETHER DIETHYL ETHER DIETHYL ETHER CHCL3 OILS OILS TOLUENE 01 ETHYL ETHER CHCL3 OCTANOL OCTANOL 01 ETHYL ETFER DIETHYL ETFER CHCL3 CHCL3 OILS 8 EN2 EN TOLUENE OCTANOL 0 1 ETHYL ETHER DIETHYL ETHER OCTANOL OCTANOL D I ETHYL ETHER 0 1 ETHYL ETHER CHCL3 OCTANOL OCTANOL 01 ETHYL ETHER CHCL3 DIETHYL ETFER DIETHYL ETHER OILS OCTANOL CHCL3 DIETHYL ETHER CHCL3 DIETHYL ETHER DIETHYL ETbER CHCL3 OCTANOL OCTANOL DIETHYL ETHER 01 ETHYL ETHER DIETHYL ETkER o I E T n y L ETHER DIETHYL ETHER DIETHYL EThER DIETHYL ETHER DIETHYL ETHER CHCL~ CHCL3 CHCL3 CHCL3 CHCL~ CHCL3 OILS OILS OILS
3
46 213 36 194 182 194 14 195 195 5 192 46 209 29 46 29 214 192 113 46 40 188 43 113 46 209 215 42 43 40 42 42 43 42 43 41
0.31 0.12 -1.02 -0.94 -0.92 -0.12 -0.91 -0.87 -0.16 -0.30 -0.34 -0.48 -0.69 -0.44 0.41 0.64 -1.14 -0.72 -1.41 -1.37 -1.55
=
A A A A A A
-0.78
-0.11 -0.69 -0.51 -0.67 -0.64 -0.53 -0.18 -0.43 -0.64 -0.81 0.41
=
A P A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A
0.68
0.18 0.56 -0.01 0.29 0.24
-0.18
0.41 0.42
10 .6
0.47 0.48 0.41 0.14 0.45 -0.28 -0.01 -0.53 0.24 -0.05 -0.19 -0.11 -0.28 0.05 0.06 0.11 1.83
0.39
0.02 0.37 -1.67 -1.35 -1.92 -1.10 -1.45
-1.60
-2.00 -2.12 -1.14 -1.14 -0.85 1.15 -2.56 -1.36 0.63 0.63 0.60 -0.96 -0.66 -0.75 -1.16 -0.21 -1.96 0.41 0.32
12
-0.33
0.61 0.67 0.65 0.34 0.62 0.42 0.04 -0.12 -0.57 0.41 0.32 0.84 0.41 0.50 0.83 0.31 0.50 -0.34
3
188 174 114 214 10
188
112 112 9 216
12
=
=
A A A A A A
3
112 112 29 209 29 29 186
0.86
0.83 -0.82 -0.19 -0.46 -1.08 -1.22 -0.34 -0.22 -1.49 -0.52 -0.53 -1.02 -1.03 -0.96 -1.05 -0.19 1.23 -0.20 -2.54 -2.54 -3.33 -0.90 -3.79 -0.48 0.11 0.14 0.18 0.81 -0.11 -0.31 -0.35
0.87 A
=
A A
3
201 2 10 56
-0.08
-1.19 -0.52 -0.53 -0.78 -0.79 -0.29 -1.05 -0.19 1.20 0.42 -1.41 -1.41
=
A A N
3
113 113 210 2 10 112 112 2
=
A N
3
2 211 211 114 114 112 46 112 218 5 190 32 32
B 8
A B A A N
-1.81
-0.90 0.43 0.16 0.28 1.41
-0.11
-0.31 -0.19 -0.15 -0.18 -0.20 -0.15 -0.18 -0.17 -0.18 0.15 -0.09 -0.16 -0.24 -0.31 -0.20
= =
A A A A A A A A A A
3 111
112 46 40 66 36 51 45 112 46 40 219 209 220 193
-0.30
-0.33 -0.36
-0.30
-0.34 -0.34 -0.34
-1.19
-1.54 -1.52 -1.60 -1.70 -1.58 -1.30 -1.52 -1.51
A
A A A A A A
0.06
0.19 -0.25
CZHZCL3N101 C2H2F3N101 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H204 C2H3BR102 C2H3BR102 C2H3BR102 C2 H3 B R 102' C2H3BR102 C2H3ER102 C2H38R102 C2H38R302 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL 1 0 2 C2H3CLlO2 C2H3CL102 C2H3CL102 C2H3CLlO2 C2H3CL102 C2H3CL102 C2H3CL102 C2H3CL302 C2H3CL302 C2H3CL302 C2H3CL302 C2H3CL302 C2H3CL302 C2H3CL302 C2H3F102 C2H3F102 C2H3F301 C2H3F301 C2H31102 C2H3I 1 0 2 C2H31102 C2H3I 1 0 2 C2H31102 C2H3I 1 0 2 C2H31102 C2H3N1 C2H3N1 C2H3N103 C2H48RlN101 C2H4CLlN101 C2H4CLlN101 C2H4CL1N 1 0 1 CZH4CLlN101 C2H4FlN101 C2H4IlN101 C2H4N2.52 C2H4N2 5 2 C2H4N4 C2H4N4 C2H4N4 C2H4N402S2 C2H4N402S2 C2H401 C2H4Ol C2H40lSl C2H4OlSl C2H401S1 C2H402 C2H402 CZH402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402
T R ICHLOROACETAMIOE T R IFLUOROACETAHIOE OXALIC ACID OXALIC ACID O X A L I C ACID OXALIC ACID OXALIC ACID OXALIC ACID OXALIC ACID OXALIC ACID OXALIC ACID OXALIC AClO OXALIC ACID OXALIC ACID BROMOACETIC ACID BROHOACETIC ACID BROHOACETIC ACID BROMOACETIC ACID BROMOACETIC ACID BROMOACETIC ACID BROMOACETIC ACID
2 ~ 2 ~ 2 - T R I 8 R O M O - l ~ l - E T H A N E O I O /BROMALHYORATE/ L CHLOROACETIC ACID CHLOROACET I C A C IO CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACET I C ACI 0 CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACET I C ACI 0 CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID CHLOROACETIC ACID 1-ETHANEOlOL/CHLORALHYORATE/ 2r 2.2-TRICHLORO-lr 29 21 2-TRICHLORO-lr 1-ETHANEDIOL/CHLORALHYORATE/ 21 21 2-TRICHLORO-lr 1 - E T H A N E D I O L / C H L O R A L H Y O R A T E / 2~2~2-TRICHLORO-1~1-ETHANEDlOL/CHLORALHYORATE/ 2~2r2-TRICHLORO-lrl-ETHANEOIOL/CHLORALHYORATE/ 2.21 2-TRICHLORO-lr 1 - E T H A N E D I O L / C H L O R A L H Y O R A T E / 21 2 ~ 2 - T R f C H L O R O - l * 1 - E T H A N E O I O L / C H L O R A L H Y O R A T E / FLUOR0 ACETIC A C 10 FLUOROACETlC ACID ETHANOL, 27 21 2-TRIFLUORO 2*2.2-TRIFLUOROETHANOL IODOACETIC ACID 1000ACETIC ACID 1000ACETIC A C I O IOOOACETIC ACID IODOACETIC ACID I O W A C E T I C ACID IOOOACETIC ACID ACETONITRILE A TON I T R l L E C OXAHIC ACID BROHOACETAHIOE CHLOROACETAMIOE CHLOROACETAMIOE CHLORO A C TAM I OE CHLOROACETAMIOE FLUOROACETAMIOE IO 00 AC E T AM I DE OXAMIOEIOITHIO OXAMIOEI D I T H I O CY ANOGUAN IOINE/DICYAND P n I o E / CYAb4OGUANIDINE/OICYANO PHIOE~ CYANOGUANIOINE/OICYAND A M I D E / 2-AHINO-lr 3 r 4 - T H I A O I A Z O L E - 5 ~ S U L F O N A M I O E 2-A~INO-1~3r4-TH1AOIAZOLE-5-SULFONAMlOE ACETAL DEHY O E ACETAL OEHY DE THIOACETIC ACID THIOACETIC ACIO THIOACETIC ACID ACETIC ACID ACETIC ACID
ACETIC ACID ACETIC ACID ACETIC ACID
ACETIC ACETIC ACETIC ACETIC
ACIO ACID ACID ACID

NO. 301 SOLVENT BENZENE BENZENE BENZENE BENZENE BENZENE BENZENE N-BUTANOL I-BUTANOL SEC-BUTANOL XYLENE TOLUENE NITROBENZENE NITROBENZENE PRIM. PENTANOLS PRIM. PENTANOLS PRIM. PENTANOLS PRIM. PENTANOLS ETHYL ACETATE CCL4 CCL4 01-I-PR. ETHER 01-I-PR. ETkER 01-I-PR. ETHER 01-I-PR. ETHER HEXANE 2-BUTANONE ME-I-BUT.KETONE OLEYL ALCOIIOL 0-NITROTOLUENE CYCLOHEXANOL S-P ENTANOL S S-PENTANOLS CSZ cs2 PARAFFINS BROMOFORM OCTANOL DIETHYL ETbER OLEYL ALCOHOL OILS OILS OCTANOL DIETHYL ETHER OCTANOL DIETHYL ETbER DIETHYL ETPER CHCL3 OILS DIETHYL ETHER N-BUTANOL SEC-BUTANOL S-PENTANOL S 0 1 ETHYL ETbER OILS OILS OILS OCTANOL DIETHYL ETbER CHCL3 OCTANOL OCTANOL CCL4 DIETHYL ETHER OILS DIETHYL ETHER DIETHYL ETtER OCTANOL OIETHY~ ETPER DIETHYL ETbER DIETHYL ETHER CYCLOHEXANE CYCLOHEXANE CHCL3 OILS OILS OILS OILS OILS BENZENE BENZENE BEN ZEN CCL4 HEXANE OLEYL ALCOHOL REF FOOT NOTE 51 45 14 40 16 66 190 184 190 42 42 14 48 190 184 182 177 194 45 14 190 221 40 222 14 190 195 5 48 LOGP SOLV -1.97 -1.80 LOGP OCT -0.56 -0.32 -0.59 -0.79 -0.64 -0.33 -0.40 -0.42 0.40 -0.29
A A A A A A A A A

EMPIRICAL FORMULA C2H402 CZH402 C2H402 CZH402 C2H402 CZH402 CZH402 C2H402 C2H402 CZH402 CZH402 C2H402 CZH402 C2H402 C2H402 CZH402 C2H402 CZH402 C2H402 C2H402 CZH402 CZH402 CZH402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 C2H402 CZH402 C2H402 CZH402 CZH402 C2H402 CZH403 CZH403 CZH403 CZH58R1 CZH5CL1 CZH511 CZH511 CZH5N101 C2H5N101 CZH5N101 CZH5N101 CZH5N101 CZH5N102 C2H5N102. CZH5N102 C2H5N102 CZH5N102 C2H5N102 CZH5N102 CZH5N102 CZH5N102 CZH5NlS1 CZH5NlS1 CZH5N302 C2H5N302 C2HbF 1 0 3 P 1 CZHbN201 CZHbN201 C2H6N202 C2H6N2S1 C2H601 C2HbOl C2H601 C2H601 C2H601 C2H601 CZH601 CZH601 CZHbOl CZH601 CZH601 CZH601 CZH601 CZH601 C2H601 C2H601 C2HbOl CZH601 ~ ~ ~ 6 0 C2H60151 C2HbOlSl C2Hb02 CZH602 CZH602 C2H6S2 C2H7N1 CZH7N1 CZH7N1 C2H7N1 CZH7N1 C2H7N1 CZH7N1 C2H7N1 C2H7N1 NAME ACETIC ACID ACETIC ACID ACETIC ACIO ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC A C I O ACETIC A C I D ACETIC ACIO ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC A C I D ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACIO ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID ACETIC ACID HYOROXYACETIC ACIO/GLYCOLIC ACID/ HYOROXYACETIC ACIO/GLYCOLIC ACID/ HYOROXYACETIC ACID /GLYCOLIC ACID/ ETHYL BROMIDE ETHYL CHLORIDE ETHYL IODIDE ETHYL IODIDE ACETAL OOX IME ACETAMIDE ACET AM I O ACETAMIOE AC ET AM IOE AMINOACETIC AC IO/GLYC I N / AMINOACETIC ACIO/GLYCINE/ AMINOACETIC ACIO/GLYCINE/ AMINOACETIC AC IOlGLYC I NE/ 0-METHYL CARBAMATE 0-METHYL CARBAMATE 0-METHYL CARBAMATE 0-METHYL CARBAMATE NITROETHANE THIOACETAMIOE THIOACETAM I OE 1-METHYL- 1-NITROSOUREA 1 2 3 9 0 9 1 1-METHYL-1-NITROSOUREA (239091 01 METHYLFLUOROPHOSPHATE METHYL UREA METHYL UREA METHYLOLUREA METHYLTHIOUR EA ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL ETHANOL 01HETHYLSULFOX I O OIMETHYLSULFOXIOE E T H A N E - 1 ~ 2 - O I O L / E T H Y L E N E GLYCOL/ ETHANE-1.2-OIOL/ETHYLENE GLYCOL/ ETHANE-lr2-OIOL/ETHYLENE GLYCOL/ OIMETHYLOISULFIOE 0 1 METHYL AM 1NE DIMETHYLAMINE OIMETHYLAMINE 0 1 METHYLAMINE 0 1 METHYLAMINE OIMETHYLAMINE ETHYL AM I N ETHYLAMINE ETHYLAMINE
302
303 304 3c5 306 30 7
-2.00
12 -2.20 -2.05 -1.74 0.09 0.07 0.08 -1.92 -1.90 -1.44 -1.42
30 8
309 3 10 311 3 12 3 13 3 14 3 15 3 16 3 17 3I 8 3 19
-0.09
-0.32
-0.32
-0.42 -0.34 -0.44
-0.02
-0.03
-0.03
-0.04 -0.18 -1.92 -2.45 -0.73 -C.77 -0.77 -0.61 -2.84 0.08 -0.32 -0.66 -1.48 -0.06 0.16 -0.03 -2.83 -2.62 -1.32 -1.58
-0.35
-0.24 0.22 -0.23 -0.31 -0.31 -0.35 -0.17 0.47 -0.35 -0.09 -1.18 -0.11 -0.34
320
321
A A
A
322 323
324 325 3 26 327 328 3 29 3 30
223
190 195 14 165 197 47 5 192 5 224 224 186 3 56 3 112 112
12
331 332
333 3 34 3 35 336 337 338 339 3 40 341 342 343 344 345 346 347 348 349 3 50 351 352
12
-1.11
-1.55 -1.70 1.57 1.38
-1.11
-1.23 -1.13 1.74 1.54 2.00 2.27 -0.13 -1.46 -1.46 -1.26 -1.58 -1.71 -3.03 -1.92 -2.39 -0.63 -0.26 -0.04 -0.04 0.18 0.36 -0.46 -0.16
=
A
E 8
20 .0
50
2.45 -0.13 -2.60
=
A
=
8 8 N A A
-2.60 -2.00
12 19 -3.08 -2.08 -1.81 -1.01 -1.82 -0.85 -1.60 -1.40 -1.40 0.18 -0.55 -1.14 -0.16 -0.03
2
192 225 84 195
353
3 54
355
3 2
224 214 186 112 112 226 227 226 3
356
357 358 359 3 60 361
A A A A
=
8 N
-0.03
-0.09 -1.75 -1.84 -2.98 -1.31
=
8 A A A A
362 3t 3
364 365 366 367 368 369 370 371 372 373 374 375 376
-0.04
-2.92 -3.36 -3.55 -1.64
2
3 198 5 3 198 174 82 229 174 2 30
-0.32
12 -0.58 0.28 -0.57 -2.37 -1.96 -0.85 -1.52 -1.45 -1.45 -1.49 -1.33 -1.58 -1.49 -0.01 -1.61 -2.26 -1.00 -1.84 -2.03 -1.51 -1.93 -2.27 -3.31 1-17 -1.22 -0.82 0.10 -0.68 -1.08 -1.28 -1.18
-0.32
-0.39 0.37 -0.38 -0.18 -0.19
=
A A A
N A A A A A A
173 101
-0.13
-0.11 -0.17 0.00 -0.18 -0.09 1.37 0.47 -0.43 -2.03 -1.93 -1.88 -1.79 1.77 -0.23
377
378 379 380 381 382 383 384 3e5 386 387 388 389 390 391 392 393 394 395 396 357 398 399 400
200
70 82 231 232 233 82 82
12 12
A A
csz
233
9 234 9 3 12
OCTANOL CCL4 OCTANOL OIETHYL ETHER OILS OCTANOL o i E T n y L ETFER BENZENE I-BUTANOL XYLENE TOLUENE TOLUENE DIETHYL ETHER XYLENE TOLUENE
=
=
A
2
235 3 205 184
=
E 8 8 8 E 8 E
-0.02
-0.38 -0.10 -0.12 -0.27 -0.19 -0.08
46
205 68 3 46 68
-0.66
-1.28
-0.27
NO.
SOLVENT OCTANOL 01 ETHYL ETHER PRIM. PENTANOLS OCTANOL OCTANOL OCTANOL OIETHYL ETFER CHCL3 OIETHYL ETHER CHCL3 OCTANOL OCTANOL OCTANOL 01 ETHYL ETHER D I E T H Y L ETHER D I E T H Y L TI-ER CHCL3 BENZENE OCTANOL OCTANOL DIETHYL ETHER OIETHYL ETkER CHCL3 XYLENE OILS OCTANOL OCTANOL DIETHYL TI-ER ME-I-8UT.KETONE DIETHYL ETHER 01 ETHYL ETHER CHCL~ CHCL3 XYLENE OLEYL ALCOHOL 0 1 ETHYL ETHER DIETHYL ETPER OIETHYL ETHER D I E T H Y L ETI-ER DIETHYL ETI-ER N-BUTANOL I-BUTANOL PRIM. PENTANOLS ETHYL ACETATE HEXANOL ME-I-BUT.KETONE OLEYL ALCOFOL S-PENTANOL S N-BUTANOL PRIU. PENTANOLS HEXANOL OCTbNOL DIETHYL EThER DIETHYL ETPER DIETHYL ETFER CHCL3 OILS BENZENE XYLENE TOLUENE CHCL3 OILS BENZENE TOLUENE OILS OlLS DIETHYL ETHER DIETHYL ETHER CHCL3 OILS BENZENE .TOLUENE CHCL3 CHCL3 BENZENE XYLENE TOLUENE 0 1 ETHYL ETHER 0 CT ANOL OCTANOL OILS OILS OCTANOL DIETHYL EThER OILS D I E T H Y L EThER I - EUTANOL OCTANDL PARAFFINS OCTANOL DIETHYL ETbER CYCLOHEXANE CHCL3 OILS OILS OILS BENZENE BEN2 ENE BENZENE BENZENE
REF FOOT NOTE
L06P SOLV
LOGP OCT
EMPIRICAL FORMULA
NAME ETHANOLAMINE ETHANOLAMINE PHOSPHATE t MONOETHYL IMIDAZOLEI 21 4r S-TRI8ROMO IMIOAZOLEIZ~~~ 5-TRICHLORO IMIOAZOLEI 2.49 5-TRIIOOO MA LONON1TR I L E MALONONITRIL E ACETYLENE CAR8OXYb I C ACIO/PROPIOLIC A C I O I AC ETYL ENE CARBOXYL I C A C I OlPROP I O L IC AC I O / I PROPANOL, 2v2*3r3r+PENTAFLUORO A t RYLONI R I L E T ISOXAZOLE CYANOACETIC A C I D CYANOACETIC A C I D CYANOACETIC A C I D CYANOACETIC A C I D CYANOACETIC A C I O THIAZOLE L A2 AUR AC I A 8-018ROMOPROPIONIC A C I D I A 8-DIBROMOPROPIONIC A C I D , A~&OIBROMOPROPIONIC A C I D A i 8-OIBROMOPROPIONIC A C I D 1.3-OICHLOROACETONE PYRAZOLE HYDANTOIN ACRYLIC A C I D ACRYLIC A C I D A-KETOPROPION I C A t I D/P YR UV I C ACIO/ A-KETOPROPIONIC AC I O / P YRUV I A C I D / C A-KETOPROPIONI C AC I D / P YRUVIC ACIO/ A-KETOPROPIONIC AC I O/P YRUVIC A C I D / A-KEl,OPROPIONIC D/P YRUVIC ACID/ AC I A-KETOPROPIDNIC AC I O / P YRUV I C A t I D/ UALONIC A C I D MALONIC A C I D UALONIC A C I D MALONIC ACID MALONIC A t 1 0 MALONIC A C I D MALONIC A C I D MALONIC A C I D MALONIC A C I D MALONIC A C I D UALONIC A C I D MALONIC ACIO MALONIC A C I D PHOSPHOGLYCERATE AN ION PHOSPHOGLYCERATE ANION PHOSPHOGLYCERATE ANION A-BROMOPROPIONIC A C I D A-BRDMOPRDPIONIC A C I D A-BROMOPRDPION I C A C I D A-BROMOPROPIONIC A C I D A-BROMOPROPIONIC A C I D A-BROMOPROPIONIC A C I D A-BROMOPROP ION I C A C I D A-BROMOPRDP I O N I C AC I O A-BROMOPROPIONIC A C I D 8-BROMOPRDPIONIC A C I D 8-BROMOPROPIONIC A C I D 8-8ROMOPROPIONIC A C I D 8-BROMDPROPIONIC ACIO 2r3-PROPANEOIDL DINITRATEvl-CHLORO CHLOROACETONE A-CHLOROPROP I O N I C A t I O B-CHLOROPROPIONIC A C I D 8-CHLOROPRDPIONIC A C I D B-CHLOROPROPIONIC A C I D B-CHLOROPROPIONIC AC IO 8-CHLDROPROPIONIC ACID B-IOOOPROPIONIC A C I D 8-IDDOPROPIONIC A C I D B-IODOPROPION I C AC IO 8-IODOPROPIDNIC A C I D 8-IODOPRDPIONIC A C I D 8-IOOOPROPIONIC AC I D 0 PROPIONITRILE PR O P IONI TR I L E GLYCERYL T R I N I TRATE GLYCERYL T R I N I T R A T E 1 (2-CHLOROETHYL I - 1-N I TROSOUREA (NCS 4 7 5 4 7 I DIMETHYL CYANAMIDE OX METHYL CYANAUI DE MALONDI AMIDE UALONDIAMIDE
401 402 403 404 405 406 407 408 409 4 10 411 4 12 4 13 4 14 415 4 16 4 17 418 4 19 420 421 422 423 4 24 425 426 427 428 429 4 30 431 432 433 434 435 4 36 437 438 439 440 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 456 457 458 459 4 60 461 462 4t3 464 465
466
5 3 236 206
206
50
17
206
237
231
112 112
9
5 56 207 112 66 112 66 218

218
-1.31 -2.89 -0.18 1.96 1.18 2.78 0.04 -0.53 0.40 -1.85 1.23 -0.92
-1.31 -1.71
-0.53 1.96 1.18 2.78
*
8
= =
A N A A
01 .5
0.11
0.46
-0.46 1.23 -0.92 0.08 -0.33 -0.26 -0.26 -0.75
0.63
0.08
-0.52
= =
A A A A A
-0.43
-0.44
-2.17 12
-0.76
0.44 0.22
0.44
02 .2
0.72 1.69 0.84 1.13 0.21 0.13 -1.69 0.43 0.31 -0.43 -0.24 -0.75 0.29 0.13 -0.35 -0.75 -0.81 -0.68 -0.18 -0.66 -0.91
= =
A A A A
207
46 46 46
06 .8
12
1.79 -0.42
-0.60
-0.28 0.13
-1.69
173
238
56 192 195 112 46 112
= =
A A A A A A A A A A A
0.36
0.40 -0.62 -0.41 -2.18 -1.02 -1.52 -0.92 -0.99 -1.08 -0.91 -0.34 -0.89
46
46 5 212 207 194 46
64
194
48
-0.28
-0.11 -0.22
48 194 74 195
-0.66 -0.58
-0.75
-0.65
-0.51 -0.73 -1.28 -0.43 -0.40 0.11
5
195
-0.68 -0.70 -0.80
181 181 181 5 3 207

46
10 10 18
-0.52
0.92 1.18 1.04 1.50 -0.44 -0.18 -0.62 -1.01 -0.80 -0.61 -0.34 -0.85 -0.97 2.16
A A A A A A A A A A 0.54 A 0.71 A 2.14 8 0.28 B 0.96 A 06 .6 A 0.44 A 0.76 A 0.33 A 0.49 A 0.85 A 0.93 A 0.86 A 0.89 A 0.95 A 1.13 A 0.16 = 0.04 = 2.05 8 2.35 8 0.57 = -0.18 A -0.50 B -2.87 A -1.99 0.92 1.15 1.03 1.44 0.82 1.08 0.76 0.69 0.86 0.65 0.91
CZH7N101 CZH7N10 1 C2H7WP1 C3HIBR3N2 C3HlCL3N2 C 3 H l I 3N2 C3HZN2 C3H2N2 C3H202 C3H202 C3H3F501 C3H3N1 C3H3NlOl C3H3N102 C3H3N102 C3H3N102 C3H3N102 C3H3N102 C3H3NlSl C3H3N302 C3H4BR202 C3H48R202 C3H48R202 C3H48R202 C3H4CLZD1 C3H4N2 C3H4N202 C3H402 C3H402 C3H403 C3H403 C3H403 C3H403 C3H403 C3H403 mi404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H404 C3H407P1 C3H407P1 C3H407P1 C3H5BR102 C3H5BR102
467 468 4 69 470 471 472 4 13 414 415 476 477 478 479 480 481 482 483 484 4E5 486 487 488 489
4 90
29 2 09 29 46 29 29 209 29 29 239 173 207 207 29 2 09 29 29 29 46 29

46
0.03
0.95
0.62
-0.86
-0.53
-1.06
C3H5BR102 C3H58R102 C3H5BR102 C3H58R102 C3H5BR 1 0 2 C3H5CLlN206 C3H5CL101 C3H5CL102 C3H5CL102 C3H5CL102 C3H5CL102 C3H5CL102
-1.23 -0.40 -0.32

-0.52 -0.82
29 46 186
-0.68
1.15
0.16
5
239 240 227 2 2
3
4 238 241
12
0.04 2.04 2.06 0.57 -0.34 -1.14 -3.52 -1.06 -0.66 -1.79
-0.24
-0.66
-0.24
491
492
5 3
242 243
=
A
50
12
493 454 495

496
230
173 70 51 182 2 44 42 12
457 458 499 5 00
12 12 12
-0.21 -0.96 0.72 -0.70 -1.10 -0.64 -0.04 -0.03 -0.04 0.00
-0.06
0.39 -0.14 -0.47 -0.09 0.52
8
B
8
B 8
0.51 0.52 0.55
8 B
8
C3H5N309 C3H5N309 C3HbCLlN302 C3HbN2 C3H6N2 C3HbN202 C3HbN202 C3H6N2S 1 C3HbN2S1 C3H601 C3H601 C3H601 C3H601 C3H601 C3H601 C3H601 C3H601 C3H6D1 C3H6D1 C3H601
IMIOAZOLIODNE~2-THIO/ETHYLENETHIOUREA/ I M IOAZOL IODNE. 2-THIDIETHYLENETHI OUREAI AC ETONE ACETONE ACETONE ACETONE ACETONE ACETONE ACETONE ACETONE ACETONE ACETONE ACETONE
NO. 501 502 503 504 505 506 5c7 5C8 509 5 10 511 5 12 513 5 14 5 15 5 16 5 17 518 5 19 520 521 522 523 524 525 526 527 5 28 52 9 5 30 531 532 533 534 5 35 536 5 37 5 38 539 5 40 541 542 543 5 44 545 546 547 548 5 49 550 551 552 553 55 4 555 556 55 7 558 559 5 60 561 562 5t3 564 565 566 567 568 569 570 571 572 573 514 575 576 577 578 579 5 80 581 582 583 58 4 5E5 586 587 588 589 5 90 591 592 593 594 595 596 597 598 5 99 600
SOLVENT TOLUENE CCL4 CCL4 CCL4 HEXANE CSZ CL 3CCHCL2 CL ZCHCHCL 2 CLZc=CCLZ CLZC=CHCL OCTANOL DIETHYL ETHER CHCL3 DIETHYL ETHER OCTANOL DIETHYL ETHER OILS BENZENE CCL4
REF FOOT NOTE 188 51 243 37 242 242 243 243 243 2 43 56 174 174
LOGP SOLV
LOdP OCT 0.43
EMPIRICAL FORMULA
NAME ACETONE AC ETDNE ACETONE ACETONE ACETONE AC TON E ACETONE ACETONE ACETONE AC TONE ALLYL ALCOHOL ALLYL ALCOHOL ALLYL ALCOHOL PROP IONALOEHYOE ACETIC ACID, METHYL ESTER ACE1 I C ACIO.METHYL ESTER ACETIC ACIOIMETHYL ESTER ACETIC A t 1 0 1 METHYL ESTER ACETIC ACIOIHETHYL ESTER ACETIC ACIDvMETHYL ESTER PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC ACID PROPIONIC A C I D PROPIONIC ACID PROPIONIC ACIO PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C l O PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC ACID PROPIONIC A C I D PROPIONIC A C I D PROPIONIC AClO PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC ACID PROPIONIC A C I D PROPIONIC A C l O PROPIONIC A C I D PROPIONIC A C I D PROPIONIC ACID PROPIONIC ACIO PROPIONIC ACID PROPIONIC ACID PROPIONIC ACIO PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC ACID PROPIONIC ACIO PROPIONIC A C I D PROPIONIC ACID PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D PROPIONIC A C I D A-HY OROXYPROP I O NI C AC ID l L A C T I C A t IO/ A-HYOROXYPROPIONIC A C I O l L A C T I C ACID/ A-HYOROXYPROPIONIC A C I D /LACTIC A , D CJ / A-HYOROXYPROPIDNIC A C I O l L A C T I C ACID/ A-HYOROXYPROPIONIC ACIO/LACTIC ACID/ A-MYDROXYPROPIDN I C A t 1 D l L A C T I C AC 101 A-HYOROXYPROPIONIC ACIO/LACTIC A C I D / ON O/L A CT I AC I O/ C A- HY OR OXYPROP I 1C AC I A-HYOROXYPRDPIONIC ACIO/LACTIC A C I D / A-HYOROXYPROPIONIC AClD/LACTIC ACID/ A-HYOROXYPROPlONIC ACIO/LACTIC A C I D / A-HY OROXYPROPIDNIC AC 10 /LACTIC A C I D / A-HYOROXYPRDPIOhIC ACIO/LACTIC A C I D / A-HYM(OKVPROP1OhIC A C I D /LACTIC ACIO/ A-MY OROXYPROP I O N I C A C I O/LACT I C A C I O I METHOXYACETIC ACID METHOXYACETIC A C I D METHDXYACETIC ACID METHOXYACETIC A C I D METHOXYACETIC A C I D Ar~OIHYDROXYPROPIONIC ACIO/GLYCERIC A C I D / 1-BROHOPROPANE GLYCEROL HONOCHLOROHYORIN GLYCEROL HDNOCHtOROHYDRIN GLYCEROL-A-HONOCHLOROHYDRIN DIMETHYLFORHAHIOE OIMETHYLFORMAH I D E N-METHYLACETAMIOE PROPI O NAMI DE PROPO AM I IN DE PROPIONAMIOE AMINOACETIC ACID, METHYL ESTER
12
12
-0.31 -0.37 -0.35 -0.34 -0.92 -0.52 0.22 0.63

-0.55 0.05 0.17 -0.12 -0.51
3 5 3
0.30
50
0.18 0.43
2
245
-0.37
12 0.47 0.41 0.26 0.33 0.25 0.13 0.20
245
245 218 5 190 207
cs2
OCTANOL OCTANOL DIETHYL ETHER DIETHYL EThER DIETHYL ETPER DIETHYL ETHER DIETHYL ETHER DIETHYL ETt-ER CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 OILS OILS B EN2ENE BENZENE BENZENE BENZENE N-BUTANOL I-BUTANOL I-BUTANOL S EC-BUTANOL XYLENE XYLENE TOLUENE ZENE
112
46 49
0.23
0.18
0.23
0.27 -0.78 -0.79 -0.79 -0.85 -0.80 -0.80 -0.85 -1.20 -1.16 -1.37
36
51 14 48 112 29 209 193 51 44 14 29 190 184 48 190 48 46 51 29 14 48 190 48 194 14 48 190 221
-1.22
0.51 0.51 0.43 0.39 -1.32 -1.24 -1.34 -1.33 -0.80 -0.75 0.54 0.37
ETHYL ACETATE CCL4 CCL4 DI-I-PR. ETHER DI-I-PR. ETHER 01-I-PR. ETHER 2-BUTANONE HE- I-BUT. KETONE OLEYL ALCOHOL ETHYL BROMIDE 0-N I TROTOL UENE OECALIN S-PENTANOLS S-PENTANOLS PARAFFINS PARAFFINS OECALIN OCTANOL DIETHYL ETHER D I ETHYL ETHER DIETHYL ETPER DIETHYL TI-ER DIETHYL ETHER 01 ETHYL ETHER CHCL3 CHCL3 I-BUTANOL PRIM. PENTANOLS PRIM. PENTANOLS HE-I-8UT.KETONE OLEYL ALCOHOL S-PENTANOLS DIETHYL ETHER DIETHYL ETHER CHCL3 ME- I-BUT .KETONE S-PENTANOLS DIETHYL ETHER OCTANOL DIETHYL ETHER OILS OIETHYL ETPER 01 ETHYL ETHER OILS OCTANOL DIETHYL ETHER CHCL3 OILS DIETHYL ETHER
2 22 190
195 5 48 48 48 190 195 14
197
246
12
5
51 247
112
46 49 2 13 112 46 184 247 48 195 5 195 207 112
0.35 -1.79 -1.62 -0.09 -0.09 -0.01 0.40 0.21 -0.09 -0.70 -0.86 -1.44 0.58 0.49 -2.15 -1.28 -1.56 -0.62 -1.09 -0.99 -0.96 -0.64 -1.09
-1.07 -2.23 -1.81

-0.10 -0.32 -0.40 -0. BO
-1.21
-0.31
-0.76
12 -0.62 -1.30 -0.57
112
195 195
-0.30
-2.05 2.10 -1.10 -1.92 -1.10 -1.62 -2.31 -1.05 -1.B9 -1.40 -2.44 -1.14
3
186 2 2 3 2 2 2 35
3
248 2
50
C3H601 C3Hb01 -0.25 8 C 3 H 6 0 1 -0.36 8 C 3 H 6 0 1 C3H601 C3H601 C3H601 C3H601 C3H601 C3H601 0.17 = C 3 H b 0 1 0.02 A C3HbO1 0.13 N C 3 H b 0 1 0.38 A C 3 H 6 0 1 0.18 = C3H602 0.49 A C3H602 0.20 B C3H602 0.87 8 C3H602 0.32 8 C3H602 C3H602 0 . 3 3 = C3H602 0.25 = C3H602 0.23 A C3H602 0.29 A C3H602 0.31 A ~ 3 ~ 6 0 2 0.27 A C3H6D2 0.33 A C3Hb02 0.35 A C3HbD2 0.52 A C3H602 0.51 A C3H602 0.50 A C3H602 0.45 A C3H602 0.49 A C3Hb02 0.51 A C3H602 0.42 A C3Hb02 0.25 A C3H602 0.24 A C3H602 0 . 0 3 A C3Hb02 0.18 A C3H602 C3H602 0.19 0.22 C3H602 0.10 C3HbDZ C3H602 0.44 C3H602 0.44 A C3H602 0.39 A C3H602 0.40 A C3H602 C3H602 0.21 C3H602 0.28 C3H602 0.30 0.16 ~ 3 ~ 6 0 2 0.32 C3H602 0.33 A C3H602 0.46 A C3H602 0.44 C3H602 0.41 C3H602 0.47 C3HbOZ C3H602 0.14 0.14 C3H602 0.46 C3H602 C3Hb02 C3H602 C3Hb02 C3H602 0.36 0.25 C3H602 C3H602 C3Hb02 C3H602 -0.62 = C3H603 -0.84 A C3H603 -0.74 A C3H603 -0.73 A C3H603 -0.44 A C3H603 -0.84 A C3Hb03 - 0 . 8 2 A C3H603 -0.81 A C3Hb03 -0.43 A C3H603 -0.65 C3H603 C3H6D3 -0.81 C3H603 -0.81 C3H603 -0.74 -0.64 C3H603 C3Hb03 -0.66 -0.55 A C3H603 -0.43 A C3Hb03 0.04 A C3H603 C3H603 -0.58 -0.65 C3H603 -1.68 A C3H604 2.10 = C3H7BR1 -0.85 A C3H7CL102 4 - 5 5 A C3H7CL102 -0.85 A C3H7CL102 -0.59 B C3H7NlDl -0.87 A C 3 H 7 N 1 0 1 -1.05 = C3H7N101 -0.81 B C3H7N101 -0.70 N C3H7N10 1 -0.99 A C3H7N101 -0.88 A C3H7N102
NO. 601 602
SOLVENT OCTANOL 01 ETHYL ETHER N-BUTANOL SEC-BUTANOL OCTANOL DIETHYL ETHER OILS OILS OILS OILS OILS 0 1 ETHYL ETHER OCTANOL CYCLOHEXANE CHCL3 TOLUENE CCL4 OCTANE cs2 OILS OCTANOL N-BUT ANOL PRIM. PENTANOLS HEXANOL OCTANOL N-BUTANOL PRIM. PENTANOLS HE XANOL PRIM. PENTANOLS OILS DIETHYL ETCER DIETHYL ETPER DIETHYL ETCER OlLS 0 1 ETHYL ETPER OCTANOL DIETHYL ETCER DIETHYL ETHER CYCLOHEXANE CHCL 3 OILS OILS OILS OILS BENZENE BEN7 EN . HEXANE OLEYL ALCOHOL DIETHYL ETPER DIETHYL TI-ER CHCL3 OILS OILS OCTANOL 0 1 ETHYL ETPER OILS DIETHYL ETPER OILS 0 1 ETHYL ETFER DIETHYL ETPER DIETHYL TI-ER OILS OCTANOL DIETHYL ETCER XYLENE TOLUENE OCTANOL DIETHYL TI-ER OIETHYL ETHER DIETHYL ETHER CYCLOHEXANE CHCL3 CHCL3 8 EN Z EN E BENZENE I -BUTANOL XYLENE TOLUENE TOLUENE TOLUENE CCL4 01-I-PR. ETHER OCTANOL DIETHYL E T H E R PRIM. PENTANOLS OCTANOL DIETHYL E T P E R I-BUTANOL OIETHYL Ell-ER OCTANOL OCTANOL N-BUTANOL DIETHYL ETI-ER OCTANOL CHCL3 OCTANOL N-BUTANOL OCTANOL DIETHYL Ell-ER CHCL3
REF FOOT
NOTE
LOGP SOLV -2.94 -5.85
LOGP OCT -2.94 -5.00 -2.74 -1.82 -0.15 -0.04 0.22 -0.15 0.44 0.30
EMPIRICAL FORMULA
NAME A-AMINOPROPIONIC A C I O I A L A N I N E I A-AMINOPROPION I C ACIOIALAN I N / A-AMINOPRDPIONIC ACIO /ALANINE/ A-AMINOPROPIONIC ACIO /ALANINE/ 0-ETHYL CARBAMATE/URETHANE/ 0-ETHYL CARBAMATE/URETHANE/ 0-ETHYL CARBAMATE/URETHANE/ 0-ETHYL CARBAMAT EIURETHANEI 0-ETHYL CARBAMATE/URETHANE/ 0-ETHYL CARBAMATEIURETHANEI 0-ETHYL CARBAMATE/URETHANE/ A-HYDROXYPROPIONAM IDE/LACTAMIOE/ 1-NITROPROPANE 1-NITROPROPANE 1-NITROPROPANE 1-NITROPROPANE 1 - N I TROPROPANE 1-NITROPROPANE 1- NI TROPROP AN E GLYCERYL MONONITRATE 8-GLYCEROPHOSPHATE ANION 8-GLYCEROPHOSPHATE ANION 8-GLYC EROPHOSPHATE AN ION 8-GLYCEROPHOSPHATE ANION L- A-GLYCEROPHU SPHATE ANION L-A-GLYCEROPHOSPHATE ANION L-A-GLYCEROPHOSPHATE ANION L-A-GLYCEROPHOSPHATE ANION SERINE PHOSPHATE N t N-0 I ME THYL UR EA OIMETHVLUREAtSYM. 0 I METHYLUR E A t UN S YM ETHYLUREA ET HYLUREA ETHYLTHIOUREA PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROPANOL PROP AN OL PROPANOL I -PROPANOL I-PROPANOL I - PROPANOL I PROP ANOL I-PROPANOL 01 METHOXVMETHANE METHOXYETHANOL METHOXYETHANOL 1.2-PROPANEOIOL l r 2-PROPANEDIDL TRIMETHYLENE GLYCOL GLYCEROL GLYCEROL GLYCEROL ISOPROPYLAMINE PROPYL AMINE PROPYL AM INE PROPYL AMINE TRIMETHYLAMINE TRIMETHYLAMINE TR IMETHYLAMINE TRIMETHYLAMINE T R IMETHYLAMINE T R IMETHYLAMINE T R IMETHYLAMINE TRIMETHYLAMINE TR IMETHYLAMINE TRIMETHYLAMINE TRIMETHYLAMINE TR IMETHYLAMINE TRIMETHYL AMINE TRIMETHYLAMINE TR IMETHYLAMINE TRlMET HYLAMINE 2- PROPANOL I 1- AMINO 2-PROPANOL, 1-AMINO PHOSPHATE, MONO-N-PROPYL PHOSPHORIC A C I O I TRIMETHYL ESTER l r 2-PROPYLENEOIAM INE 193-OIAMINOPROPANOL-2 193-OIAMINO-PROPANOL-2 5-FLUOROURACIL ( 1 9 8 9 3 1 B U T A N O L I Z ~ ~ I~ * ~ ~ ~ v ~ ~ ~ - H E P T A F L U O R O AZAXANTHINE 1.2-OIBROMOSUCCINlC A C I O PYRlMIOlNE SUCCINOOIN I T R I L E 2- THIOURACIL URACIL BAR8ITURIC A C I D BARBITURIC ACID BARBITURIC ACID
56 3
225 84 218 3 2 173 82 214 249 3 186 250 2 50 250 2 50 2 50 2 50 240 181 181
=
A
12 19
603
604 605 606
-.0 16
-0.94 -0.15 -0.19
=
A
A A A
6C7
6C8 609 6 10 611 6 12 613 6 14 615 6 16
6 17
-1.12
-0.92 -1.52 -0.85
0.38 A
A
A
-1.00
-2.74 0.65 0.53 1.91 1.40 0.99 0.45 0.85 0.45 0.28 -0.70 0.04 -0.04 0.43
-2.28
0.65 2.41 1.67
=
N B
12
618 6 19 620 621 622 623 6 24 625 626 627 628 6 29 6 30 631 632 633 6 34 635 6 36 6 37 6 38 6 39 6 40 641 642 643 644 645 646 647 648 6 49 6 50 651 652 653 6 54 655 656 6 57 6 58 6 59 660 661 662
1.46
181
181 181 181 181 181 181
10 10 10
16 10
0.28
0.43
10 10 18 10
-0.70
0.21
0.18
-0.22 -2.64 -2.51 -2.54 -2.39 -2.77 -1.35 0.34 0.28 -1.17 -2.07 -2.10 -1.97 -1.29 -1.06 0.34
2
3 3
3
2 198 186 3 174 82 174 173 101 200 201 82
A A A A A A
-0.03
-1.49 -0.21 -0.85 -0.81 -0.89 -0.81 -0.87 -0.65 -1.48 -0.45 -0.19 -0.33 -0.35 -1.32 -1.05 0.00 -0.82 -2.25 -1.74 -2.77 -2.00 -3.18 -2.96 -4.15 -0.03 -0.54
0.36 0.10
0.41 0.42 0.45
= A
A
N A A A A A
0.38
0.45 0.48 0.74 0.12 -0.04 -0.16
23L
82 82 2 174 174 2 20 1 5 3 2
0.28
0.00 0.24 0.00
A A N A A
=
A A A A A A A A
-0.60
-0.82 -1.41 -1.30 -1.64 -2.66 -2.47 -2.56
3 2 3 3
198
2
218
663
664 665
666
-0.03
0.37 0.21 0.15
=
8
3
46
-0.36
-0.65 0.27 -0.34 -0.26
8
B
68
251 3 251 188 251 2 51 46 205 251 184 205 205 68 188 251 25 1 5 3
667
0.27
0.54 0.61 0.52
=
8 8 B 8 B
8
668
669 670 671 672 613 674 675 676 677 678 679 6 80 68 1 682 683 614 6E5 686 687 688 689 690 691 692 693 694 65 5 696 657 698 699 700
-0.38
-0.44 0.54 0.59
0.23
0.27 0.31 0.35 0.18 1.45 0.40 0.40 0.42 0.66 0.10 -0.96 -1.22 -0.38 -0.52 -1.77 -1.80 -2.44 -0.95 1.81 -0.46 1.63 -0.40 0.35
-0.33
-0.29 0.49 -0.44
8 8 8
-0.36
-0.36 -0.34 -0.09 -0.36 -0.96
8
8 N
=
8
8 8 =
50
17
-2.37
-0.06
236
56
-0.52
-2.94 -0.92
3
4 3 226 9 252
-3.70
-0.95
38
212 2 38
188
1.81 0.04 1.73 -0.40
=
A
=
N
235
253 2 18 192 2 54
70
36
-0.23 -0.28
-0.40 -1.47 -1.63 -2.10
-0.28
-1.07 -1.47 -1.32
=
A N
-1.32
C3HIN102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7N102 C3H7NlO2 C3H7N102 C3H7N102 C3HTNlO2 C3H7N105 C3H706P1 C3H706P1 C3H706P1 C3HTO6P1 C3H706P1 C3H706Pl C3H706 P1 C3H706P1 C3H8N106Pl C3H8N201 C3H8N201 C3H8N201 C3H8N201 C3HBN201 C3H8NZS1 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H801 C3H802 C3H802 C3H802 C3H802 C3H802 C3H802 C3H803 C3H803 C3H803 .~ C3H9Nl C3H9Nl C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9N1 C3H9Nl C3H9N101 C3H9N101 C3H904P1 C3H904P1 C3H10N2 C3HlON201 C3HlON203 C4H3FlN202 C4H3F701 C4H3N502 C4H48R204 C4H4N2 C4H4N2 C4H4NZOlS1 C4H4N202 C4H4N203 C4H4N203 C4H4N203
1, 562 Chemical Review's, 1971 Vol. 71, No. 6
NO.
253 65 227 212 207 46 4 194 194 194 194 195 195 212 207
46 4
SOLVENT N BUT ANOL OCTANOL OCTANOL DIETHYL E T H E R DIETHYL ETHER DIETHYL ETWER I-BUTANOL ETHYL ACETATE CYCLOHEXANONE 2-BUTANONE ME-I-8UT.KETONE ME- I-BUT.KETONE S-PENTANOL S DIETHYL ETkER DIETHYL E T P E R DIETHYL ETHER I-BUTANOL ME-I-8UT.KETONE OLEYL ALCOHOL S-PENTANOLS OCTANOL DIETHYL ETHER DIETHYL ETHER I-BUTANOL XYLENE OCTANOL OCTANOL OIETHYL ETkER DIETHYL ETHER CHCL3 OILS OILS OCTANOL N-BUTANOL OCTANE OCTANE N-BUTANOL OCTANOL OCTANOL CHCL3 OCTANOL OILS OILS OILS OILS OCTANOL OCTANOL DIETHYL E T k E R DIETHYL ETHER CHCL3 CHCL3 BENZENE XYLENE TOLUENE OCTANOL 01 ETHYL ETI-ER DIETHYL ETkER DIETHYL ETHER 01 ETHYL ETkER DIETHYL ETHER DIETHYL ETHER D I ETHYL ETPER D I ETHYL ETHER CHCL3 N-BUTANOL I-BUTANOL PRIM. PENTANDLS PRIM. PENTANOLS ETHYL ACETATE CYCLOHEXANONE HEXANOL 2-EUTANONE ME-I-BUT.KETONE ME-I-6UT.K ETONE S-PENTANDLS DIETHYL ETHER DIETHYL ETHER I-BUTANOL ME- I-6UT.K ETONE S-PENTANOL S OCTANOL D I ETHYL ETHER DIETHYL ETHER I-BUTANOL OLEYL ALCOHOL S-PENTANOLS ME-I-BUT-K ETDNE DIETHYL ETHER DIETHYL ETHER D I ETHYL ETHER DIETHYL ETCER I -BUTANOL PRIM. PENTANOLS S-PENTANOL S ME-I-BUT.KETONE OILS OCT ANOL CHCL3 OILS BENZENE
REF FOOT NOTE
LOGP SOLV
LOGP OCT
EMPIRICAL FORMULA C4H4N203 C4H4N204 C4H4N601 A C4H404 A C4H404 A C4H404 C4H404 C4H404 C4H404 C4H404 C4H404 C4H404 C4H404 A C4H404 A C4H404 A C4H404 C4H404 C4H404 C4H404 C4H404 = C4H4S1 A C4H5BR104 A C4H5BR104 C4H5ER104 A C4H5ER104 = C4H5F302 = C4H5N1 A C4H5NlD2 A C4H5N102 C4H5NlOZ A C4H5N102 8 C4H5N1S1 = C4H5N3 C4H5N301 C4H5N302 C4H5N302 C4H5N303 = C4HbN40151 C4HbN403S2 C4H6 N403 S2 = C4HbN40352 8 C4HbN4012 B C4H601 8 C4H601 8 C4H601 = C4H601S1 = C4H602 A C4H602 A C4HbDZ A C4H602 A C4H602 A C4H602 A C4Hb02 A C4H602 = C4H604 A C4Hb04 A C4H604 A C4H604 A C4Hb04 A C4H604 A C4H604 A C4H604 A C4H604 A C4H604 C4H604 C4Hb04 C4H604 C4Hb04 C4H604 C4H604 C4H604 C4H604 C4H604 C4H604 C4H604 A C4HbO5 A C4H605 C4H605 C4H605 C4H605 C4Hb05 A C4Hb05 A C4H605 C4H605 C4Hb05 C4H605 C4H605 A C4HbD6 A C4H606 A C4H606 A C4H606 C4H606 C4Hb06 C4H606 C4H606 E C4H70R 102 = C4H7BR102 A C4H7BR102 A C4H7BR102 A C4H78R102
I
NAME BARBITURIC ACIO 3-CARBOXYMETHYLSYONONE 8-AZACUANINE (NCS 7 4 9 l ( P K A = 6.431 FUMARIC A C I D FUMARIC A C I D FUMARIC A C I D FUMARIC A C I D FUMARIC ACID FUMARIC A C I D FUMARIC A C I D FUMARIC A C I D FUMARIC ACID FUMARIC A C I D MALEIC ACID MALElC ACID MALEIC ACID MALEIC ACID MALEIC ACID MALEIC ACID MALEIC ACID THIOPHENE BROMOSUCCINIC ACID BROMOSUCCINIC ACID BROMOSUCCINIC ACID BROMOSUCCINIC ACIO ACETIC ACID, TRIFLUORO-ETHYL ESTER PYRROL E SUCC I N I M I DE SUCCIN I M I D E SUCC I N l M I D E SUCC I N I M I D E ISOTHIOCYANATEIALLYL PYRIMIDINEIZ-AMINO CYTOS I N
701 702 703 704 7c5 706 7c7 7C0 7c9 7 10 711 7 12 7 13 7 14 715 716 7 17 7 18 7 19 7 20 721 722 723 724 725 726 727 728 7 29 7 30 731 732 733 73 4 735 736 7 37 738 739 7 40 7 41 742 743 744 745 746 747 748 749 7 50 751 752 753 754 755 756 757 758 759 7 60 761 762 763 764 765 766 7 67 768 7 69 7 70 771 772 173 714
36
-1.16 -1.66
-0.71
0.19 0.10 0.07 0.76 0.23 0.54
-2.12 -1.66 -0.71 0.28 0.20 0.18
0.56
0.23
0.53 0.08 0.22

0.60 -0.82 -1.04 -0.50 0.11 -0.66 -0.89 -0.32 1.81 0.46 0.84 0.75 -1.44 1.18 0.75 -1.51 -1.42 -1.27 -2.31 2.02
0.41 0.07 0.20
0.38
-0.61 -0.79 -0.32 -0.35 -0.66
195
5
195 255
-0.32
-0.67 1.81 0.52 0.86 0.55 0.22 1.18 0.75
212
46 4 46 218 186
3
113 113 2 173 218 253
-1.21
-1.13
-0.58
-0.91 2.11 -0.22 -1.46
-2.65 0.38 -0.25
-0.22
36
36 07 07
256 2 56
253 134 217 217 218 240 257
12
258 259
260 261 192 46 29 46 29
46
-0.68 -1.47 -1.60 -1.54 0.38 -0.25 -2.39 -0.26 2.51 1.66 0.40 1.61 0.60 0.72
2-METHVL-5-NITROIMIOAZOLE
4-METHYL-5-41TR01MIOAZOLE URWIL 3~METHYLTHIO-4-AMINO-lrZ14-TRlhLINE-5-ONE 2-ACETYLAMINO-1~3~4-THIAOIAZOLE-5-SULFO\AMIOE ~-ACETYLAMINO-II 3 9 4-THIAOIAZOLE-5-SULFOhAMIOE 1~3r4-THIADIALOLE-2-SULFONAMIDEr5-ACETAMIOO ERYTHRI TOL TETRAN ITRATE O I V I N Y L ETHER D I V I h Y L ETHER O I V I N Y L ETHER G-THIO8UTYROLACTONE CROTONIC A C I D CROTONIC A C I D CROTONIC ACID CROTONIC ACIO CROTONIC A C I D CROTONIC A C I D CROTON I C AC I D CROTONIC A C I D SUCCINIC ACID SJCCIhIC ACID SJCCIhIC ACID SUCCINIC A C I D SUCCINIC A C I D SUCCINIC A C I D SUCCINIC A C I D SUCCINIC A C I D SUCCINIC A C I D SUCCINIC ACIO SUCCINIC A C I D SUCCINIC A C I D SUCCINIC ACIO SUCCINIC A C I D SUCCINIC A C I D SUCCINIC A C I D SJCCINIC ACIO SJCCINIC ACID SUCCINIC A C I D Sr)CCINIC A C I D SUCCINIC ACIO OIGLYCOLIC A C I D D I U Y C O L I C ACID OIGLYCOLIC A C I D OIGLYCOLIC ACIO DIGLYCOLIC A C I D MALIC A C I D MALIC ACID MALIC ACID MALIC ACID MALIC A C I D MALIC ACID 0-L-MAL I C A C I D TARTARIC A C I D TARTARIC K t 0 TARTARIC A C I D TARTARIC I C 1 0 TARTARIC A C I D TARTARIC A C I D TARTARIC A C I D D-TARTARIC A C I D BROMDACETIC ACID. ETHYL ESTER A-EROMO8UTYRIC A C I D A-8ROMOBUTYRIC AC I D A-BROMOBUTYRIC A C I D A-BROMOBUTYRIC A C I D
-0.26
2.76 1.81 0.77 1.77 0.60
0.72 0.55
-0.50
0.72 0.74 0.61

0.76
-0.56
-0.91 -1.05 -1.05 -0.59 -0.87 -0.82 -0.89 -0.90 -0.65
0.71
0.48 0.64 0.64 -0.59 -0.64 -0.60 -0.66 -0.67 -0.45 -0.61 -0.62
29
5
212
3 192 194
46
62
213
-0.83
-0.84
36
46 194
-0.86
-1.92
-0.63
0.00
-0.02 -0.15 -0.19
715 776 777 7 78 779 7 80 781

702 783 784 785
4 182 48 194 194 74 194 194 195 195
-0.53 -0.51 -0.53

-0.59 -0.54 -0.77
-0.80
-0.63
0.04 -0.34 0.00 -0.73 -0.69 -0.23
-1.52 -1.54
3 207
4 195 195 5 207
-0.31 -1.27 -.2 06

-1.26 -1.88 -1.85 -0.63 -1.74 -0.97 -1.36 -2.43 -1.01 -2.42 -2.34 -0.78 -1.21 -1.10
786
787 788 7 89 790 791 792 793 794 795 796 797 790 799 800
213 4 5 195 195 192 46 2 13

36 46
12
-0.68 -2.14 -0.69 -0.57 -1.22 -1.24 -0.94 -1.18 -1.02 -1.26 -1.53 -1.49 -1.39 -1.16 -1.42 -1.27 -2.02 -0.76
-2.01
-1.93 -1.60 -1.84 -1.56 -1.47 1.35 1.42 1.29 1.12
195 195 173 5 29 209

29
-1.58 1.12 1.42
00 .8
0.14 -0.08
1.31
NO. 801
SOLVENT I-BUTANOL TOLUENE OCTANOL DIETHYL ETHER CYCLOHEXANE CHCL3 BENZENE N-BUTANOL ETHYL ACETATE N-BUTYL ACETATE CCL4 N-HEPTANE 2-BUTANONE OCTANE CS2 OCTANOL OILS OILS OILS DIETHYL ETHER CHCL3 PRIM. PENTANOLS DIETHYL ETHER CHCL3 ETHYL ACETATE ME-I-BUT.KETONE S-PENTANOLS OCTANOL N-BUTANOL OCTANOL OILS OCTANOL OCTANOL DIETHYL ETHER CYCLOHEXANE CHCL3 BENZENE N-BUTANOL ETHYL ACETATE N-BUTYL ACETATE CCL4 N-HEPTANE 2-BUTANONE
REF FOOT
NOTE
LOGP SOLV 1.46 -0.27 1.40 1.36 0.55 1.43 1.46 1.65 1.48 1.48 0.92 0.36 0.72
LOGP OCT 1.55 1.32 1.40 2.06 1.93 1.56 1.83
EMPIRICAL FORMULA
NAME A-BROMOBUTYRIC ACID A-BROMOBUTYRIC ACID DICHLOROVINYLPHOSPHONATE~OiO-DIMETHYL
802 803
804 805 806 8C7 808 809 810 811 812 813 814 815 816 817 818 819 820 821 822
4 29 262 26 2 26 2 262 2 62 262 262 26 2 2 62 26 2 262 262 262
=
N 8
1.53
1.52 2.06 0.81 N
0.30
0.71 2.03 1.36 0.20 1.53 1.23
218
224 214 173
2.03
2.44 1.37 1.68 1.21 0.65 2.70
=
A A 8 A N
A
112
112 263 207 67 67 195 195 260 253 56 264
0.08
2.38
12 -2.18 -2.78 -1.56 -1.50 -0.88 -0.05 -0.31 -3.20 -0.15 0.34 0.51 -0.29 -1.70 -0.10 -0.82 0.93 0.40 0.45 -1.40 -2.00 0.08 -2.00 -1.70 0.52 -0.95 -1.08 -1.32 0.61 0.29 0.26 1.20 0.83 0.70 1.04 -0.30 0.73 0.66 0.93 0.40 0.60 1-01 0.86 0.95 0.72 0.79 0.66 0.68 0.66
823
824 825 826 827 828 829
-1.80
-1.73 -1.40
-1.31
-0.05 -0.95 -3.20 1.05 0.34 0.51 0.59
0.51 0.57 0.81 0.37 0.85 0.67 -0.52 0.52 -0.29 -2.16 -2.35 0.94 0.29 0.26 1.18 1.20 1.02 1.04 0.19 0.73 0.66 0.93 0.79 0.94 1.25 0.70 2.68 0.79 0.69 0.71 0.69 0.82 0.97 0.97 1.05 0.87 0.82 0.74 0.73
=
=
A
36 12
830
831 832 833 834 835 836 837
238
262 262 262 262 262 262 262 262 2 62 262 2 62 262 262 238 265 266 253 267 186 5 4 259 267 268 258 186 5
=
8
N A
838
839 840 841 842 843
=
N
36
852 853 854 855 856 857 858 859 860 861 862 863 864 805 866 867 868 869 870 871 872 873 874 875 876 877 878 879 880 881 882 883 8e4 885
886
887 888 889 890 891 892 893
894
8S5 896 897

898
899 900
OCTANOL I-BUTANOL OILS OILS OCTANOL OILS OCTANOL OCTANOL DIETHYL E l k OILS OILS BENZENE I-BUTANOL CCL4 CS2 OCTANUL DIETHYL ETtER DIETHYL ETHER DIETHYL ETHER DIETHYL ETHER HCL3 CHCL3 OILS OILS OILS BENZENE BENZENE N-BUTANOL I-BUTANOL I-BUTANOL I-BUTANOL SEC-BUTANOL XYLENE TULUENE NITROBENZENE PRIM. PENTANOLS PRIM. PENTANOLS PRIM. PENTANOLS ETHYL ACETATE CCL4 DI-I-PR. ETHER 2-BUTANONE OCTANE OLEYL ALCOHOL 0-NITROTOLUENE S-PENTANOLS PARAFFINS DOOECANE HEXADECANE
= =
8 8
=
B
= =
A B B 8
3
2 224 245 4 245 245 5 190 207 46 49 29 46 209 220 193 44 29 190 4 184 48 190 46 29 48 190 184
48
50 12
=
0.81
-0.27 -0.27 -0.21 -0.35 -0.46 -0.65 -0.65 0.95 0.97 0.96 0.91 0.72 -0.78 -0.82 -0.42
0.85
0.86 0.85 0.78 0.48 0.93 0.84 0.50 0.95 0.93 1.00 0.72 0.99 0.83 0.78 1.02 0.86
A A
1.05
0.97 10 .3 0.72 -1.02 0.24 0.70 -1.76 0.46 -0.44 1.01 -1.15
194 48 221 190 60 5 48 190 197 60
A A
47
60 ~. 4 7
-1.87
-1.92
47
C4H7BR102 C4H7BR 1 0 2 C4H7C L 2 03P 1 C4H7CL203Pl C4H7CL203Pl C4H7C L2 03P 1 C4H7CL203Pl C4H7CLZ03P1 t4H7CL203Pl C4H7CLZ03P1 C4H7CL203Pi t4H7CL203Pl C4H7CLZO3P1 C4H7CL203P1 C4H7CLZ03P1 C4H7CL301 C4H7CL301 C4H7CL302 C4H71102 C4H7N102 C4H7N102 C4H7N102 C4H7N103 C4H7N103 C4H7N103 C4H7N103 C4H7N103 C4H7N1 S 1 C4H7N5 C4H7NA102 C4H88RlN101 C4HBBRlN101 C4HBCL304Pl C4H8CL304Pl C4H 8C L 3 0 4 P 1 C4HBCL304Pl C4H8CL304P1 CCH8CL304Pl C4H8CL304P1 C4HBCL304Pl C4H 8C L 3 0 4 P 1 C4H8CL304P1 C ~ H B C L ~ O ~ P ~ C4H8CL304P1 C4H8CL304Pl C4H8N2 C4HBN2 0 2 C4HBN202 C4H8N6 C4H801 C4H801 C4H8Ol C4H801 C4H801 C4H801 C4H801 C4H801 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4HB02 C4H802 C4H802 C4H802 C4H802 C4H802 ~ 4 ~ 8 0 2 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C~HBOZ C4H8D2 ~ 4 ~ 8 0 2 C~HBOZ C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 ~ 4 ~ 8 0 2 C4H802 ~ 4 ~ 8 0 2 C4H8OZ ~ 4 ~ 8 0 2 ~ 4 ~ 8 0 2 ~ 4 ~ 8 0 2 C4H802
DICHLOROVINYLPHOSPHONATEiO~O-OIMETHYL DICHLDROVINYLPHOSPHONATE~O~O-OIMETHYL DICHLOROVINYLP~SP~"ATEIO~O-OIMETHYL B~8~B-TRICHLORO-T-8UTANOL 6 1 BI 8-TR ICHLORO-1-BUTANOL A.A.8-TRICL-N-BUTYRALDEHYDE HYDRATE I O W A C E T I C A C I O . ETHYL ESTER D I ACE1 Y LMONOX I M E DIACETYLMONOXIME 0 I C E T Y L MONOX 1ME A ACETIC ACID, ACETYLAHINO/ACETYL GLYCINE1 ACETIC ACID, ACETYLAM INOlACETYL GLYC I N / ACETIC ACID. ACETYLAMINOlACETYL GLYCINE/ ACE1 I C ACID, ACETYLAMINOIACETYL GLYCINE/ ACE1 I C ACID, ACETYL AM IkO/ACETYL GLYCINE / 2-AZACYCLOPEhTANTHIONE 4r 5.6-TRIAMINOPYRIMIOINE BJTYRIC ACID, SODIUM SALT A-BROMO-I-BUTYRAMIOE BROMOACETAMIOEIN-ETHYL O I M E - ~ - O H - ~ I Z ~ ~ - T R I C L E T H Y LPHOSPHONATE/DIPTEREX/ O I M E - ~ - O H - Z I ~ ~ ~ - T R I C L E T H Y LPHOSPHOhATE/OIPTEREX/ DIME-l-OH-2~2r2-TRICLETHYL PHOSPHOhATEIOIPTEREXI 0 1 ME-1-OH-2.21 2-TR I C L ETHYL PHOSPhOhATE / 0 1 P TEREXl OIME-1-0H-21212-TRICLETHYL PHOSPhOhATE/OIPTEREX/ 01ME-l-On-2,212-TR ICLETHYL PHOSPHOhATE/DIPTEREX/ P 0 1 ME-1 -OH-21 2 t 2-TR 1CL E ThYL P HO SPHONA T E / D I TE RE X I DIME-1-OH-21 21 2-TR ICL E ThYL PHOSPHONATE/OI PTEREXl D I M E - l - O H - 2 ~ 2 ~ 2 - T R I C L E l H Y L PHOSPHOkATEIDIPTEREXI 01 ME-1 -OH- 2 e 2 t 2- TR I E Th YL PHOSPHOkATE / 01 P T E R E X I CL D I M E - 1 - 0 H - 2 ~ 2 1 2-TRICLETHYL PHOSPHOhrATE/OIPTEREX/ 0 1 ME-1-OH-2, 2r 2-TR I C L E THYL PHOSPhOhATE/OI PTERE X / DIME-1-OH-2121 2-TR ICLETHYL PHDSPHONATE/OI PTEREX/ 2- 1M 1 D AZOL 1NE v 2-ME THYL OIMETHYLGLYOXIHE 0 I METHY LCL Y OX I M E TETRAMINOPYRIM I O I N E ALLYL METHYL ETHER 2- 8U T A NONE 2- BUT A k ON E 8JT YRAL DEdY DE C Y C L O P R O P Y L METHYL ETHER CICLDPROPYL METHYL ETHER ETHYL VINYL ETHER ETHYL VINYL ETHER ACETIC ACID, ETHYL E S T E R ACETIC ACIOI ETHYL ESTER ACETIC ACIDIETHYL ESTER ACETIC ACID, ETHYL E S T E R ACETIC ACIDIETHYL E S T E R ACETIC ACI0,ETnYL ESTER A C E T I C ACIO~ETHYL S T E X ACETIC ACID,ETHYL ESTER ACETIC ACID,ETnYL ESTER BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID 8JTYRIC ACID BUTYRIC ACID BJTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACID BUTYRIC ACIO
564 Chemical Reviews, 1971, Vol. 71,

SOLVENT CHCL3 CHCL 3 OILS BENZENE BEN Z ENE BENZENE XYLENE TOLUENE TOLUENE NITROBENZENE P R I M . PENTANOLS CCL4 OCTANOL CCL4 OCTANOL DIETHYL ETHER DIETHYL ETkER OCTANOL DIETHYL ETHER I-BUTANOL OLEYL ALCOHOL DIETHYL E T t E R DIETHYL EThER P R I M . PENTANOLS DIETHYL ETPER OCTANOL OCTANOL 01 ETHYL ETCER OILS I-BCTANOL OCTANOL OCTANOL 0 1 ETHYL ETPER N-BUTANOL I-BUTANOL SEC-BUTANOL OCTANOL OCTANOL OCTANOL OILS CCL4 CCL4 OCTANOL 0 1 ETHYL Ell-ER I-BUTANOL DIETHYL ETkER OCTANOL DIETHYL ETHER DIETHYL ETkER CYCLOHEXANE CYCLOHEXANE CHCL3 OILS OILS BENZENE BENZENE BENZENE CCL4 HEXANE OCTANE OLEYL ALCOHOL OOOECAN E HEXAOECANE OCTANOL OC T ANOL 0 1 ETHYL ETPER DIETHYL ETPER CHCL3 OILS OILS OILS I-BUTANOL OCTANOL DIETHYL Ell-ER DIETHYL ETHER CHCL 3 OILS OILS OCTANOL 01 ETHYL ETl-.ER DIETHYL ETHER CHCL3 OILS OILS OILS OCTANOL OCTANOL DIETHYL ETFER OILS OILS
No. 6
LOGP OCT 1-00 0.96 1.13 0.69 0.71 0.58 0.91 0.88 0.82 0.50 0.95 0.61 -0.42 -0.23 -0.18 EMPIRICAL FORMULA NAME I-BUTYRIC ACID I-BUTYRIC ACID I-BUTYRIC ACID I-BUTYRIC A C I O I-BUTYRIC ACID I-BUTYRIC ACID I-BUTYRIC ACID I-BUTYRIC A C I D I-BUTYRIC A C I O I-BUTYRIC ACID I-BUTYRIC A C I D I-BUTYRIC ACID DIOXANE DIOXANE FORMIC ACID, PROPYL ESTER BUTYRIC AC 101 8-HYDROXY ETHOXY A C E 1 I C A C I D A-HY OROXY- I-BUTYRI C A C I O A-HYDROXY-I-BUTYRIC I C 1 0 A-HYDROXY-I-BUTYRIC A C I O A-HYDROXY-I-BUTYRIC A C IO A-HYOROXYBUTYR I C ACID A-HYDROXYBUTYRIC ACID A- H OR0 XYBUT Y R I C A C I O V LACTIC ACIOvMETHYL E S T E R I-CHLOROBUTANE BUTYRAMIOE BU TY R A M I DE BUTYRAMIOE BUTYRAMIDE NI N-01 M ETHYL A C ET AM I DE MORPHOLINE A-AMINOBUTYRIC A C I D A-AMINOBUTYRIC ACID A-AMINOBUTYRIC ACID A- AM I N 0 BUTY R I C A C I O 2-METHY L-2-NITROPROP AN E 2-METHYL-2-NITROPROPANE BUTYL NITRATE 0 1 ETHYLFLUOROPHOSPHATE 01 ETHYLFLUOROPHOSPHATE 01 ETHYLFLUOROPHOSPHATE PIPERAZINE PIPERAZINE PIPERAZINE PROPYLTHIOUREA BUTANOL BUTANOL BUTANOL BUTANOL BUTANOL BUTANOL BUT AN0 L BUTANOL BUTANOL BUTANOL BUTANOL BUTANOL BUT AN0 L BUTANUL BUTANOL BUTANOL BUTANOL I-BUTANOL IBUTANOL I-BUTANOL I-BUTANOL I-BUTANOL I BUT ANOL I-BUTANOL I BUT ANOL I-BUTANOL S-BUTANOL S-BUTANOL S-BUTANOL S-BUTANOL 5- BUTANOL S-BUTANOL 1-BUTANOL 1-BUTANOL 1-BUTANOL 1-BUTANOL 1-BUTANOL 1-BUTANOL 1-BUTANOL ETHYL ETHER ETHYL ETHER ETHYL ETHER ETHYL ETHER ETHYL ETHER ETHYL ETHER ETHYL ETHER 1 3-BUTANEOIOL . 1 9 3-BUTANEOIOL 1, CBUTANEDIOL 1.4-BUTANEOIOL 21 3-BUTANEOIOL 2, 3-BUTANEDIOL 21 3-WTANEOIOL ETKUXYETHANOL
NO.
901 902 903 904 9c5 906 9C7 908 909 9 10 911 912 913 9 14 915 916 9 17 918 919 920 921 922 923 9 24 925 926 927 928 9 29 9 30 93 1 932 933 9 34 935 936 937 938 939 940 941 942 943 944 945 946 947 948 949 9 50 951 952 953 9 54 955 956 957 958 9 59 9 60 961 962 963 964 965 966 967 968 969 9 70 971 972 973 974 975 916 977 978 9 79 980 981 982 983 984 985 986 9 87 9 88 9 89 990 991 992 993 994 995 996 997 998 999
REF FOOT NOTE 51 29 209 51 29 46 46 51 29 48 48
LOGP SOLV -0.25 -0.28 -0.12 -0.74
A
A A A A A A A A A
-0.72
-0.81 -0.80 -0.86
-0.87
-0.42 0.99 -1.47 -0.42 -0.13
37
5 234 56 46 207 5 192 4 5 2 69 46 2 69 12
=
A A A A A A
08 .3
-0.40 -0.34
0.83 =
-0.36
-0.65 0.08
-0.36
-0.45 -0.38
-0.85
-0.48 -0.08 0.05 -0.43 2.39 -0.21 -1.24 -2.02 0.18 -0.77 -1.08 -5.58 -1.34 -1.79 -0.79
-0.28
-0.31 0.19 -0.32 -0.26 2.39 -0.21 -0.24 -0.65 -0.25
3 I86
186
= =
8 A
3
2 4 235 218
-0.77
-1.08 -4.16 -2.38 -3.02 -1.61
= =
A
3
225 4 84
12 19
65
270 2 35 271 228 271 5
1.01
1.17 2.15 0.43 0.54 0.54 -1.17 12
1.01
2.15 0.81 0.44 0.44 -1.17 -2.03 -1.36 -0.24 0.88 0.89 0.63 1.03 0.94 1-02 1.19 0.96 1.00
= =
B 8
B
=
8 A
3
4 198 216
-3.28 -0.60
-0.41 0.88 0.89 0.57 -0.72 -1.12 0.45 -0.28 -0.20 -0.19
=
A
A
3
174 272 82 174 173 201 272 82 2 31 272 82 59 82 59 59 5 216
A
A A A
-0.34
-0.38 -0.44
-0.78
12 -0.81 -0.19 -0.96 -1.08 0.83 0 65 . 0.84 0.53 0.34
0.38
0.83 0.65
=
A A N A
A
A
C4H802 C4H802 C4HB02 C4H802 C4H802 C4H802 C~HBOZ C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H802 C4H803 C4H803 C4H803 C4H803 C4H803 C4H803 C4H803 C4H803 C4H803 C4H803 C4H9CL1 C4H9N101 C4H9N101 C4H9Nl 0 1 C4H9N101 C4H9N 1 0 1 C4H9N101 C4H9N102 C4H9N102 C4H 9N 1 0 2 C4H9N102 C4H9N102 C4H9N102 C4H9N103 C4HlOF103Pl C4HlOF103P1 C4HlOF103Pl C4H10N2 C4HlONZ C4HlON2 C4HlONZSl C4H1001 c4niooi C4H1001 C4HlOOl C4HlOOl C4H1001 C4H1001 C4H1001 C4H1001 C4H1001 C4H 1 0 0 1 C4H1001 C4H1001 C4H1001 C4H1001
c~niooi
3
174 174 173
0.85 0.59
0.92 0.86 0.97 0.96 0.80 0.61 0.68 0.12 0.89
101
201 4 186
-0.36 -0.24 -0.26

0.93 0.61 0.65 0.28 0.30 -0.60 -0.42 0.37 0.34 -0.08 -0.04 -0.64 -0.74 -0.66 0.77 0.83 1.00 0.58
C4HlO01 C4H1001 C4H1001 C4H1001 C4H1001 C4H1001 C4HlOOl C4HlOOl C4H1001 C4H1001
ceniooi
3
174 174 2 201 186
0.65
0.81 0.37 0.41
3 174
174 173 224
A 0.06 A 0.57 N
0.61 0.52 0.59
A A
A
A N
201
218 5 3 173 82 258 2 59
0.77
0.83 0.99 0.93
50
03 .8
0.36 0.60 -1.38
0.78
0.74 0.93 -1.10 -0.93 -1.38 -1.22 -0.92 -1.25
-2.37
OILS OCTANOL 0 1 ETHYL ETI(ER OILS -1.72 -2.68 -0.92 -1.54 -2.47 -0.54
A 8 8 8 B A A A A
1000
~CTANOL
-i.03
-0.54
A A
C4H1001 C4H1001 C4H 1 0 0 1 C4H1001 C4H1001 C4H1001 C4H 1 0 0 1 C4H1001 C4H1001 C4H1001 C4HlOOl C4H1001 C4H1001 C4HlOOl C4H1001 C4HlOOl C4H1001 C4H1001 C4HlOOl C4H1002 C4H1002 C4H1002 C+H1002 C4H1002 C4HlOOZ C4H1002 C4H1002
NO. 1001 1002 1003 io04 1005 1006 10C7 1008 1009 1 0 10 1011 1012 1013 10 1 4 1015 1016 1 0 17 1018 1019 1020 1021 1022 1023 1024 1025 1026 1027 1028 1029 1030 1031 1032 1033 1034 1035 1036 1037 1038 1039 1040 1041 1042 1043 1044 1045 1046 1047 1048 1049 1050 1051 1052 1053 1054 1055 10 56 1057 1058 1059 1060 1061 1062 lot 3 1064 1065 1066 1067 1C68 10 6 9 1070 1071 1072 1073 1074 1075 1076 1077 1078 1079 10 80 1081 1082 lOE3 1084 1085 1086 1087 1088 1089 1090 1091 1092 1093 1094 1095 1096 1097 1098 1099 1100
SOLVENT OIETHVL ETFER OILS OILS DIETHYL ETFER OILS 01 ETHYL ETHER I -BUTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL 01 ETHYL ETHER CYCLOHEXANE CHCL3 BENZENE I-BUTANOL XVLENE TOLUENE CCL4 131-I-PR. ETHER XYLENE OCTANOL OCTANOL OCTANOL DIETHYL ETFER DIETHYL ETCER CYCLOHEXANE CHCL3 CHCL3 B EN ZEN BENZENE BENZENE N-BUTANOL I-BUTANOL I-BUTANOL XYLENE TOLUENE TOLUENE TOLUENE PRIM. PENTANOLS CCL4 CCL4 CLCHZCHZCL 01-BUTYL ETHER 01-I-PR. ETHER OCTANOL DIETHYL ETbER I-BUTANOL I -BUTANOL CCL4 PRIM. PENTANOLS 01-BUTYL ETHER DI-BUTYL ETbER CHCL3 NITROBENZENE PRIM. PENTANOLS DI-I-PR. ETHER M E - I-BUT .KETONE S-PENTANOL S DIETHYL ETkER I-BUTANCL I-BUTANOL OCTANOL OCTANOL OCTANOL OCT ANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL 3CTANOL OC T ANOL OCTANOL OCTPNOL OCTANJL OCTANOL OCTANOL N- BUTANOL N-BUTANOL OCTANOL N-BUTANOL 0 C T ANOf OCTANOL DIETHYL ETHER DIETHYL E T P E R CHCL3 CHCL3 CHCL3 BENZENE CCL4 HEXANE 0-CICL. BENZENE OCTANUL OCTANOL OCTANOL
REF FOOT NOTE 2 2 173
LOGP SOLV -0.70 -1.72 -1.15 -2.36 -2.58 -1.72 -1.43 2.28 1.95 0.88 0.81
LOGP OCT
EMP I R 1C AL FORMULA C4H1002 C4H1002 C4H1002 C4H1003 C4H1003 C4H1003 C4H1004 C4HlOS1 C4HlOS1 C4H11N1 C 4 H l lN l C4H11N1 C4HllN1 C4HllNl C4H11N 1 C4H11N1 C4H11N1 C4H11N1 C4H11N1 C4H11 N1 C4H11N1 C4H11N1 C4H11N1 C4H11N1 C4H11N1 C4H11N1 C4H11N 1 C4H11N1 C4H11N1 C4H11N1 C4HllNl C4H 1 1 N 1 C4H 1 1 N 1 C4H 1 1 N 1 C4H 1 1 N 1 C4H 11N l C4HllN1 C4H11N1 C4H 1 1 N l C4H 11N l C4HllNl C4H 1 1 N 1 C4H 1 1 N 1 C4H 1 1 N 1 C4HllN1 C4H11N1 C4HllN102 C4HllN102 C4H11N 1 0 2 C4HllN102 C4HllO2PlS2 C4H11fl4 P 1 C4H1104Pl C4H1104P1 C4H 11 0 4 P 1 C4H1104 P 1 C4H1104 P 1 C4H1104P1 C4H 110 4 P 1 C4H1104Pl C4H12N2 C4H12N2 C4H13N 1 0 1 C5C L5 N1 C5H18R3N4 C5HlCL3N4 C5HlCL4Nl C5H2CL3N1 C5H2CL3N1 C5H2CL3Nl CSH3CL2N1 C5H3CL2N1 C5H3CL2Nl C5H3CL2N1 C5H48RlNl C5H48RlNl CSH4BRlN1 C5H4CLlNl C5H4CLlNl C5H4CL 1N1 CSH4CLlN1 C5H4N401 C5H4N401 C5H4N402 C5H4N403 C 5H4N40 3 C5H4N4S1 C5HCN451 C5H403 C5H403 C5H403 C5H5F302 C5H5F302 C5H5F302 C5H5F302 C5H5F302 C5H5F302 C5H5F502 C5H5N1 CSH5N1
~~ ~
NAME ETHOXVETHANOL ETHOXVETHANOL ETHOXY ETHANOL 01 ETHYLENEGLYCOL GLYCEROL MONOMETHYL ETHER GLYCEROL, MONOMETHYLETHER ERYTHRITOL BU T ANE T H I OL 01ETHYL SUL F I OE BUTYLAMINE BUTYLAMINE BUTYLAMINE BUTYL AM I N BUTYLAM I N BUTYLAMINE BUTYLAMINE BUTYLAMINE BUTYL AM I NE BUTVLAM I N BUTYLAMINE BUTYLAMINE I-BUTYLAMINE 1 8UTY LAM INE 0 I THY L AM I N E D I ETHY LAM INE OIETHYLAMINE 01 ETHY L AM I NE D I THY LAM I N DIETHYLAMINE 01 ETHYLAMINE 01 ETHYL A M I N 01 ETHYL AMINE D I THY L AM I N E D I THY LAM I NE D I ETHYL A M I NE D I ETHYLAHINE 01 ETHYL AM I NE D I ETHYL A M I NE DIETHYLAMINE 01 ETHYL AM I N E DIETHYLAMINE 01 ETnYLAYI\E 01 THY L A H I 4 E 01 THY L A M I \ E 31 ETnVLAYICE 01 ET rlY L A'II4E D I ETHANOLAMINE DIETHANOLAMINE 0 I ETHANOL AM I N E 01 ETHANOLAMINE PHOSPHOROOlTHIOTIC ACIDIOIETHYL BUTYL PHOSPHATE BUTYL PHOSPHATE I - BUTY L PHOSPHATE DIETHYL PHOSPHATE DIETHYL PHOSPHATE D l ETHYL PHOSPHATE OIETHYL PHOSPHATE OIETHYL PHOSPHATE DIETHYL PHOSPHATE TETRAMETHYLENEDIAM INE TETRAMETHYLENEDI AMINE TETRAMETHYLAMMONIUM HYDROXIDE 2 ~ 3 . 4 9 5 9 6 PENTACHLOROPYRIOINE (PKA= -1.00) PURINEt 2, 69 8 - T R I B R O Y O PURINE, 2.69 B V - T R ICHLORO 21 31 5~6-TETRACHLOROPYRIDINE (PKA= -0.80) 2~4,6-TRICHLORUPYRIOINE (PKA= -0.30) 2 ~ 3 r 6 - T R I C H L O R O P Y R I O I N E IPKA. - 0 . 6 3 ) 2 ~ 3 5-TR I CHLOROPYRIOIN E ( PKA= 0.78 I r 216-OICHLORPYRIDINE (PKA= 0 . 3 6 1 ~ I ~ - O ~ C H L O R P Y R I O I N(PKA= 2 - 6 2 ) E 2,3-DICHLORPYRIOINE (PKA= 2 - 7 9 ] 3 r 5-OICHLORPYRIOINE (PKA= 3.201 2-BROMOPYRIOINE 3-BROMOPYRIOINE /PKA= 2.84/ 4- BROMOPYR I 0 I N E 2-CHLOROPYRIOINE (PKA= 3.33) 3-CHLOROPYRIOINE IPKA= 4 . 2 8 ) 4-CHLOROPYRIOINE (PKA= 4.57) 2-CHLOROPYR I D I N E HY POX ANTH I NE HYPOXANTHINE XANTHINE URIC ACID URlC A C I O MERCAPTOPURINE/PURINE-6-THIOL/(755) 6-PURINETHIOL HYDRATE l N C S 7 5 5 l I P K A = 7.801 FURANE-2-CARBOXYL I C A C IO FURANE-2-CAR80XVL I C ACID FURANE-2-CARBOXYL I C A C I D T R IFLUOKOACETYLACETONE TRIFLJDSDACETYLACET3NE 1.4 IFLJOROACETYLACETJhE TRIFLJS~3ACETYLACET3hE TRIFLUOROACETYLACETONE TRIFLUOROACETYLACETdNE PENTAFLUOROPROPIONIC ACID, ETHYL ESTER PYRIDINE /PKA = 5.23/ PYRIDINE
-0.50
3
2
12 12
3
4 235 186 251 218
5
251 251 251 251 4 46 150 251 25 1 46 218 2 51 5 3 251 251 251 46 205 251 46 37 4 37 46 205 68 273 182 251 37 37 37 251
0.68
0.11 -0.29 0.99 0.14 0.92 0.04 0.30 0.11 -0.04 0.10 0.40 0.57 0.43 -0.28 -0.07 -0.34 0.81 0.89 -0.02 -0.05 -0.05 0.43 0.74 0.42 -0.10 -0.09 -0.20 -0.24 0.88 0.03 -0.10 -0.05 -0.20 -0.21 -1.43 -3.27 -0.70 -0.69 0.45 0.46
A A 0.15 A -1.98 A -1.12 A -1.39 A -2.53 2.28 = 1.95 = 0.88 = 0.81 = 0.68 = 0.94 .8
-0.33
0.62 0.65 0.79 0.64 1.84 0.93 0.50 0.70 0.40 0.57 0.43 0.68 0.80 0.46 0.53 0.54 0.52 0.52
8
B A N
8 = =
8 8 8
8
8 8
0.08
0.53 0.07 0.50 0.59 0.51 0.47 0.73 0.82
8
8 8
B
5
3 4 184 135 2 36 236 2 36 274 274 236 274 274 274 3 4 184 275 206 206 275 275 275 275 2 75 275 275 275 276 276 276 275 275 275 2 76 277 253 253 277 253 227 227 192 112 112 278 2 79 279 2 79 2 79 279 218 2 76 255 50
0.30 -1.43 -2.02 -1.49
B
B
-1.48
0.36 0.28
17 17 17 17
-0.18
-0.27 -2.05 -2.14 0.23 -1.75 -0.56 0.35 -2.89 -0.12 -1.96 3.53 3.08 3.90 3.32 2.68 2.71 3.11 2.15 2.40 2.11 2.56 1.42 1.60 1.54 1.45 1.43 1.28 1.27 -1.11 -0.27 -0.34 -2.92 -0.96 0.01 0.01 0.55 0.58 -0.54 0.30 0.29 0.11
-0.65
-0.90 0.00 -1.50 -1.07 -1.69 -0.67 3.53 3.08 3.90 3.32 2.68 2.77 3.11 2.15 2.40 2.11 2.56 1.42 1.60 1.54 1.45 1.43 1.28 1.27 -1.11 -0.89 -G.99 -2.92 -1.85 0.01 0.01
12 75 27 27 75 75 75 75 75 75 75 75
= = =
= =
= = = = = = = = = = = = = = = = =
A
A A A
75 75 75 14 36 36 14 36
0.60
0.64 0.73 1.55 1.48 1.52 0.60 2.12 0.64
-0.14
-0.50
A A N
-0.05
2.12 0.64 0.65
=
= =
0.65

NO. SOLVENT REF FOOT NOTE LOGP SOL v LOGP OCT
EMPIRICAL FORMULA 0 8 8 8 C5H5N1 C5H5N1 C5H5N1 C5H5N1 C5H5N1 C5H5N1 C5H5N1 C5H5Nl C5H5N1 C5H5N1 C5H5N101 C5H5N101 C5H5N101 C5H5N101 C5H5N101 C5H5N5 C5H5N5 C5H5N5 C5H5N501 C5H5N501 C5H5N5S1 C5H5N5 S 1 C5HbNZ C5H6NZ C5H6N2 C5HbNZ C5H6NZ C5H6NZ C5HbNZOlSl C5H6N202 C5HbN202 C5Hb04 C5H604 C5Hb04 C5Hb04 C5H604 C5H7N301 C5H7N302 C5H7N501 C5H7N5S 1 C5H8 C5H8N203 C5H8N401S1 C5H8 N40 352 C5H8N403SZ C5H801 C5H801 C5H802 C5H802 C5H802 C5H803 C5H803 C5H803 C5H803 C5H803 C5H803 C5H803 C5H803 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H804 C5H9BRlNZOZ C5H98RlN202 C5H9BR102 C5H98R102 C5H9BR102 C5H9CL2N302 C5H9CLZN302 C5H9N103 C5H9N103 C5H9N103 C5H9NlS1 C5H9NlSl C5H9N309 C5H9N3010 C5HlOBRlN101 C5HlO8RlNlOl C5HlONZSl C5H1001 C5H1001 C5H1001 C5H1002 C5H1002 C5H1002 CSHlOOZ C5H1002 C5H1002 C5H1002
NAME PYRIDINE PYRlOINE PY R I 0 I NE PY R I 0 I NE PYRIOINE PY R I 01 NE PY R101NE PY R I O I N E PY R I 01 NE P Y R I D I N E lPKA= 4.901 2-HY OROXYPYR I O I N E 2-HYOROXYPYR I O I N 3- HY OROXY PYR I OI N E 3- HY OROXY PYR I 0 I N E PY R I D 1NE, 1-OX I OE ADENINE ADENINE A0 EN I N E GUAN I N E IS OGUANINE 2-TH IOAOEN I N THIOGUAN INE/Z-AMINOPUR IN- 6-THIOL/( 7 5 2 I 2- AH INOPYR IO I N 2- AH INOPYR I I N 0 3-AMINOPYRIOINE I P K A = 5.98/ 4-AMINOPYRIOINE I P K A = 9.17/ 4- AH INOPYR 10 I N E 4-METHYLPYRIMIOINE 4-HYOROXY-2-METHYLTHIO-PYRIHlOINE/2-HETHIOURACIL/ 1-HETHYLURAC I L THYMINE CITRACONIC A C I D ITACONIC ACID ITACONIC A C I D ITACONIC A C I D ITACONIC A C I D 3r 5-OIHETHYL-4-NITROSOPYRAZOLE 2-ETHYL-5-NITROIHIOAZOLE 496-01 AMINO-5-FORHAM 100-PYRI H I DINE 4 r 6-01 AM INO-5-THIOFORM A 100-PYR I M I O I NE M 1-PENTYNE UREA. 1 9 3-OIACETYL 3-HETHIO-4-AHINO-6-HE-llZ14-TRIAZINE-5-0NE 2-ACETYLIHINO-3-HE-1~3~4-THIAOIAZOLE-5-SULFONAMIDE 2-ACETYLIHINO-3-ME-lr 3r4-THIAOIAZOLE-5-SULFONAHIOE CYCLOPROPYL VINYL ETHER I-PROPENYL VINYL ETHER ACETYLACETONE ACETYLACETONE ACETYL A C E T O N E L E V U L I N f C ACIO/B-ACETYLPROPIONIC ACIOI L E V U L I N I C ACIOIB-ACETYLPROPIONIC ACID/ L E V U L f h I C ACIOIB-ACETYLPROPIONIC A C I O I L E V U L I k i C ACI0/8-ACETYLPROPIONIC ACID/ L E V U L I N I C ACIOIB-ACETYLPROPIONIC A C I O I L E V U L I N I C ACIO/B-ACETYLPROPIONIC ACID/ L E V U L I N I C ACIO/B-ACETYLPROPIONIC ACID/ L E V U L I N I C ACIO/B-ACETYLPROPIONIC A C I D / OIMETHYLHALONIC A C I D OIHETHYLHALONIC A C I D 01 HETHYLHALONIC AC I O OIHETHYLHALONIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D GLUTARIC A C I D A-BROMO-I-BUTYRYLUREA A- BROHOBUTYRLUREA A- BROHOVALER I C A C I 0 A-BROHOVALERIC AC IO A-BROHOV ALER I C A C I 0 l r 3-8ISl2-CHLOROETHYL )-l-NITROSOVREA I NC S 4 0 9 9 6 2 1 l r 3-81 S (2-CHLOROETHYL 8-1-NITROSOUREAl4099621 A-AHINOPROPIONIC A C I O i N-ACETYL A-AHINOPROPIONIC A C I O i N-ACETYL 0-ETHYL CARBAMATE, N-ACETYL 2-AZACYCLOHEXANTHIONE THIOCYANIC ACIOtBUTYL ESTER 1 i 2 1 3-PENTANETRIOLTRIN ITRATE PENTAERYTHRITOL TRINITRATE A- BROMO- I-VALERAHI OE A-BROHOVALERAH IO I M IOAZOL IDONEiN-ETHYL-2-THIO/N-ETHYLETHYLENETHIOUREA ALLYL ETHYL ETHER CYCLOPROPYL ETHYL ETHER I-PROPENYL ETHYL ETHER ACETIC ACIO1PROPYL ESTER ACETIC ACIOvPROPYL ESTER ACETIC ACIOIPROPYL ESTER ACETIC A C I O i TR IHETHYL ACETIC ACIOtTRIHETHYC ACETIC ACIOtTRIHETHYL PROPIONIC A C I O i ETHYL ESTER
01 ETHYL ETPER CHCL3 OILS BENZENE BENZENE B EN2 NE I -BUTANOL XYLENE TOLUENE OCTANOL 1111 DIETHYL ETPER 1112 CHCL3 1113 DIETHYL ETFER 1114 CHCL3 1 1 1 5 OCTANOL 1116 OCTANOL 1117 N-BUT ANOL 1118 N-BUTANOL 1119 N-BUTANOL 1120 N- 0 UT AN OL 1121 N-BUTANOL 1 1 2 2 OCTANOL 1 1 2 3 DIETHYL ETHER 1 1 2 4 I-BUTANOL 1 1 2 5 OCTANOL 1 1 2 6 OCTANOL 1127 CHCLJ 1 1 2 8 OCTANOL 1 1 2 9 OCTANOL 1130 OCTANOL 1 1 3 1 N-BUTANOL 1 1 3 2 01 ETHYL ETHER 1 1 3 3 DIETHYL ETFER 1 1 3 4 0 I ETHYL ETHER 1 1 3 5 I-BUTANOL K 1 1 3 6 ME- I - 8 U T . ETONE 1137 OILS 1138 OCTANE 1 1 3 9 N-BUTANOL 1140 N-BUTANOL 1 1 4 1 OCTANOL 1 1 4 2 OCTANOL 1 1 4 3 OCTANOL 1 1 4 4 OCTANOL 1 1 4 5 CHCL3 1146 O I L S 1147 OILS 1 1 4 8 CHCL3 1 1 4 9 BENZENE 1 1 5 0 BENZENE 1 1 5 1 DIETHYL ETFER 1 1 5 2 DIETHYL ETFER 1 1 5 3 DIETHYL ETFER 1 1 5 4 DIETHYL ETHER 1 1 5 5 CHCL3 1 1 5 6 CHCL3 1 1 5 7 I-BUTANOL 1 1 5 8 XYLENE 1 1 5 9 DIETHYL ETHER 1 1 6 0 I-BUTANOL 1 1 6 1 PRIM. PENTANOLS 1 1 6 2 OLEYL ALCOHOL 1 1 6 3 DIETHYL E T t E R 1 1 6 4 DIETHYL ETPER 1165 DIETHYL ETHER 1 1 6 6 DIETHYL EThER 1 1 6 7 CHCL3 1 1 6 8 N-BUTANOL 1169 I-BUTANOL 1 1 7 0 ETHYL ACETATE '1171 HE-I-8UT.KETONE 1172 OLEYL ALCOHOL 1173 S-PENTANOLS 1174 O I L S 1175 OILS 1176 O I L S 1177 BENZENE 1178 TOLUENE 1179 OCTANOL 1180 OECANOL 1181 CHCL3 1182 ETHYL ACETATE 1183 O I L S 1184 OCTANOL 1 1 8 5 OCTANOL 1186 O I L S 1187 OILS 1188 OILS 1189 OILS 1190 PARAFFINS 1191 O I L S 1192 O I L S 1193 O I L S 1194 BENZENE 1195 CCL4 1196 c s z 1197 DIETHYL ETHER 1198 DIETHYL ETHER 1199 I-BUTANOL 1200 OCTANOL
1102 1103 1104 1105 1106 llC7 llC8 1109 1110
1101
3
280 113
183
281
66
4 46 188 275 248 248 248 240 218 277 253 253 253 253 253 2 27 3 4 276 276 282 276 235
0.08 1.43 -0.02 0.42 0.39 0.44 0.86
0.31
75
14 36 36 36 36 36
0.16 1.04 -1.82 -1.21 -0.32 -1.40 -1.69 -0.16
0.92 0.81 0.42 0.84 0.82 0.85 0.70 0.92 0.77 1.04 -0.75 0.12 -0.16 -0.06 -1.69 -0.16
8 8
0
=
8 A A A
0.33
0.44 -0.35 -0.55
-0.07 0.09
-1.00 -1.28 -0.96 -0.07 0.75 0.41 0.11 0.28 -0.97 0.16 0.22 -1.20 -0.44 -0.43 -0.28
-0.32
-0.07
=
8
-0.11
0.65
12
70 36
0.11 0.28 -0.70

0.16 0.22
=
=
283
253
-1.20
0.05 -0.62 -0.45 -0.48 0.28 -0.26
= =
3 212 20 7 4 195 284 256 253 253 186 218 134 217 217 2 59 25 9 285 286 287 3 207 112 46
-0.31
A A A
-0.32
36 36 -0.39 -0.79 -0.02 1.98
-0.11 -0.30 0.53 8

-1.61 -0.54 1.98 -0.68 -0.16 0.13
1.95 2.04 1.90 2.14 2.25 -0.39
-0.68
-0.16 0.13 -1.40 1.83 1.94
= = = =
0 B A A A A A A A A A A A
0.77
4
0.76 0.90 -0.58 -0.64 -0.64 -0.49 -1.19
-0.45
-0.45 -0.31 0.14
112
46
-1.32
0.08 -1.90 0.44 0.69 0.71 -0.31 -0.55 -0.57 -0.60 -0.47 -1.81 0.21 0.30 -0.18 -0.45 -0.96 0.16 -0.03 -0.43 0.55 0.50 0.38 1.53 1.39 -2.20 -1.25
-0.87
4
46
0.02 -0.39
288 4 48 5 212 207 194 46 46 194 4 194 195 5 195 2 64 264 209 29 29 227 2 89 67 67 290 2 60 2 55 239 240 264 2 64 241 2 58 2 59 258 245 245 245 3 207 4 186
-0.27 0.50
0.46 0.60 0.26 -0.37 -0.39 -0.40 -0.29 -0.43 -0.25 -0.08 -0.24 -0.47 -0.39 -0.13 1.16
A A A A A
0.80
1.75 1.89
i.88
1.53
-1.40 0.40 0.13 2.03 2.10 2.44 1.00 0.63 0.69 1.43
A A A A A
0.13
20 .3
1.99
= =
8 A A A
1.38 -0.20 -0.62
-2.22
0.30 1.20 -0.21 1.52 1.59 1.30 1.51 11 .1 1.50 1.21
02 .6
12
8 B 8 1-60 8 1.39 8
A A
1.44 1.09 1.60
1.21
NO.
SOLVENT D I E T H Y L EThER OIETHYL ETHER DIETHYL ETHER CHCL3 CHCL3 OILS OILS BENZENE BENZENE N-BUTANOL I -BUTANOL SEC-BUTANOL XYLENE TOLUENE PRIM. PENTANOLS PRIM. PENTANOLS 2-BUTANONE OCTANE S-PENTANOLS PARAFFINS DODECANE HEXAOEC ANE CHCL3 CHCL3 OILS BEN2 EN 1-BUTANOL I-BUTANOL XYLENE TOLUENE NITROBENZENE PRIM. PENTANOLS CCL4 0-N ITROTOLUENE XYLENE 01 ETHYL ETCER OILS OILS I-BUTANOL OCTANOL OCTANOL OCTANOL DIETHYL TI-ER DIETHYL ETFER CHCL3 BENZENE I-BUTANOL XYLENE CCL4 OCTANOL OILS OILS OLEYL ALCOHOL DIETHYL ETkER OILS N-BUTANOL SEC-BUTANOL OILS N-BUTANOL CCL4 N-BUTANOL N-BUTANOL OILS DIETHYL TI-ER SEC-BUTANOL O C T ANOL OILS BENZENE CCL4 OCTANE OOOECANE ti EX AOECANE OCTANOL DIETHYL ETI-ER OILS OILS OILS OILS OILS OCTANOL OCTANOL OILS OILS OILS OILS OCTPNOL DIETHYL ETkER OILS DIETHYL ETHER OILS DIETHYL ETI-ER OILS I-0UTANOL XYLENE DIETHYL ETi-ER 0 C T ANOL 01-BUTYL ETI-ER OCTANOL DIETHYL ETHER I -BUTANOL
REF FOOT NOTE
LOGP SOLV
LOGP OCT
EMPIRICAL FORMULA A A A A A A A A A C5H1002 C5H1002 C5HlOOZ C5H1002 C5H1002 CSH1002 C5H1002 C5H1002 C5H1002 CSH1002 CSHlOOZ C5H1002 C5H1002 C5Hl002 C5H1002 C5H1002 CSH1002 C5H1002 CSHlOO2 C5H1002 C5H1002 C5H1002 C5H1002 C5H1002 C5H1002 C5H1002 C5HlOOZ C5HlOOZ C5H1002 C5H1002 CSHlOOZ C5H1002 C5H1002 CSH1002 C5H1002 C5H1004 C5H1004 C5 H 1004 C5H1005 C5H1005 C5H11F1 C5H11N1 C5H11N1 C5H11N1 C5HllN1 C5H11N1 CSHllNl CSHllNl C5H 11N I O l CSHllNlOl C5HllNIO1 C S t l l l h l0 1 CSHllNlOl C5HllN101 C5HllN101 C5HllN102 C5H11N 1 0 2 C5HllN102 C5H11N102 C5HllNlS2
NAME VALERIC ACIO VALERIC A C I D VALERIC A C I D VALERIC ACID VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC ACIO VALERIC A C I D VALERIC ACIO VALERIC A C I D VALERIC A C I D VALERIC ACIO VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC A C I D VALERIC A C I D I-VALERIC ACID I-VALERIC A C I D I-VALERIC ACIO I-VALERIC A C I D I-VALERIC ACIO I-VALERIC A C I D I-VALERIC A C I D I-VALER I C AC I O I-VALERIC A C I D I-VALERIC ACID I-VALERIC A C I D I-VALERIC ACIO I - V A L E R I C AICO GLYCEROL MONOACETATE/MONAC ET I N / GLYCEROL MONOACETATE/MONACETIN/ GLYCEROL MONOACETATE/MONACETIN/ ARABINOSE RIBOSE 1-FLUOROPENTANE P I P E R 1D I N E PIPERIOINE PIPERIOINE P I PERI D I N E P I PERI 01NE P I PERI 01NE PIPERIDINE 01METHYLPROP IONAMI DE MORPHOL INEI 4-METHYL VALERAM I DE VALERAMIOE VALERAHIDE I-VALERAMI OE I-VALERAHIDE A- A INOV AL EK IC AC I M OlNORVAL I NE/ A-AMINOVALERIC ACIO/NORVALINEI 0-I-BUTYLCARBAMATE VALINE N N-OIETHYLOITHIOCAR0AMIC A t 1 0 I V A L I N E HYOROCHLORIOE METHIONINE HYOROCHLORIOE NI N-OIETHYLUREA DIETHYLUREArUNSYM. ORNITHINE PE NT ANOL PENTANOL PENTANOL PENTANOL PENTANOL P ENT AN OL PENTANOL I-PENTANOL I-PENT ANOL IPENT ANOL I-PENT ANOL I-PENT ANOL 2- PENT ANOL 3-PENTANOL 1-PROPANOL, 2 1 2-DIMETHYL 2-PROPANOL, 2-ETHYLIT-AMYL ALCOHOL/ ALCOHOL/ 2-PROPANOL v 2-ETHYLIT-AMYL 2-PROPANOLtZ-ETHYLIT-AMYL ALCOHOL/ ~-PROPANOLIZ-ETHYL/T-AHYL ALCOHOL/ 2-PROPANOLp2-ETHYLIT-AMYL ALCOHOL/ 01 ETHOXYMETHANE l r 5-PENTANEOIOL 1 5- PENTAN E 0 I O L , DIETHYLENE GLYCOL MONOMETHYL ETHER DIETHYLENE GLYCOL MONOMETHYL ETHER GLYCERYL-A-HONOETHYL ETHER GLYCERYL-A-MONOETHYL ETHER PENTAERYTHRITOL AHYLAH I N E
1201 1202 1203 1204 1205 1206 12C7 1208 1209 12 10 1211 1212 1213 12 14 1 2 15 1216 12 17 12 18 12 19 1220 1221 1222 1223 1224 1225 1226 1227 1228 1229 1230 1231 1232 1233 1234 1235 1236 1237 1238 1239 1240 1241 1242 1243 1244 1245 1246 1247 1248 1249 1250 1251 1252 1253 1254 1255 1256 1257 1258 1259 1260 1261 1262 1263 lft4 1265 1266 1267 1268 1 26 9 1270 1271 1272 1273 1274 1275 1276 1277 1278 1279 1280 1281 1282 1283 1284 1285 1286 1287 1288 1289 1290 1291 1292 1293 1294 12F5 1296 1297 1298 1299 1300
190 46
49
1.24 1.17 1.36

0.34
29 46 209 220
44
29 190 184 190 46 29 190 184 190 60 190 291 60
47
0.32 0.48 0.41 -0.05 -0.09 1.36 1.39 1-06 -0.33 -0.20 1.55 1.40 1.01 -1.18
1.44 -2.54 -1.25 -1.31 0.21 0.17 0.27
1.20 1.15 1.31 1.53 1.51 1-69 1-57 1.32 1.32 1.45
1.45 0.99 1.43 1.37 1.60 1.50 1.40
A A
1.35
60
48 29 209 29 4 48
48
12 47 47
-0.23
1.30 1.13 -0.31 -0.35 0.07 1.13 -0.54 -0.05 -0.10
12 14
1.40 1.37 1.51 1.19 1.32

1.08 1.48
A A A A A A
29 40
48 48 48 46 3 214 70 4 277 186 218
1.24 0.93 1.13 1.67 -1.10 0.10 0.14 -2.92 -2.32 2.33 0.85 0.64 0.69 0.56 0.51 0.59 0.63
-0.33 0.19 0.73
-1.39 -1.22
-1.18 -1.72 -2.32 2.33
0.85 -0.24 -0.18 0.92 -0. 06 0.78 0.03 -0.82
A A A A
= =
0
8 8
13
3
46 46 183 4 46
8
A A
234 218 82 292 82
12
12
-0.33
-1.15 -0.50
3 2
225 84 293 225 294 295 295 2
19
-0.52 -0.77
-1.64 -0.98 -0.54 0.73 -1.14 0.00 -0.47 -0.40 -2.12 -1.72 -1.70 1.40 0.36 0.19 0.36 -0.19 -0.31 -0.39 1.16 1.28 0.26
0.05
0.17 -0.30 -2.02 -1.26 1.85 -2.10 -1.17 -1.07 -0.70 -0.50 -2.89 1.40 1.52 1.56
0
A A
52 52
19
A
8
3
84 216 201 231 234 59 59 59 216
=
A A
12
1.16
=
A A A A A A
3
173 101 201 201 201
186
0.33
0.32
80 173 224 296 20 1 218 2
0.17 0.20 1.36 0.89 -0.21 0.00 0.15

-0.04 0.84 -1.26 -2.21 -1.43
-2.38
1.24 1.43 1.52 1.48 1.34 1.37 1.36 0.89 1.05 1.22
=
A A A A
1.33
1.15
0.84 -0.99 -0.78 -1.14 -0.93 -1.27 -0.71 -1.70 1.05 1.13 1.33
=
A A A A A A
8
2
3
2
2
4 46
3
218 236 297 17 46 12
3
4
-1.58 -2.13 -0.85 0.44 0.30 1.33 -0.14 -3.00 -2.56 0.16
C5HlZOl C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1201 C5H1202 C5H1202 C5H 1202 C5H1203 C5H1203 C5H1203
C5H1203 C5H 12 04
C5H13Nl C5H13N1 C5H13N1 C5H 1304 P 1 C5H14IlN1 C5H14N2 C5Hl4NZ
= =
8
I-AMYL AMINE
METHYLBUTYLAHINE AMYL PHOSPHATE TRIMETHYL-ETHYL-AMMONIUM PENTAHETHYLENEOIAHINE PENTAMETHYLENEOIAMIYE IOOIOE
-3.00
-1.42 -0.28
NO. 1301 1302 1303 1304 1305 1306 1307 1308 1309 13 10 1311 1312 1313 13 1 4 13 15 13 1 6 1317 1318 13 19 1320 1321 1322 1323 13 24 1325 1326 1327 1328 1329 1330 1331 1332 1333 1334 1335 1336 1337 1338 1339 1340 1341 1342 1343 1344 1345 1346 1347 1348 1349 1350 1351 1352 1353 1354 1355 1356 1357 1358 1359 1360 1361 13t2 13t3 1364 1365 1366 1367 1368 1369 1370 1371 1372 1373 1374 1375 1376 1377 1378 1379 1380 1381 13.92 1383 1384 1385 13.96 1387 1388 1389 1390 1391 1392 1393 1394 1395 1396 1397 1398 1399 1400
SOLVENT OCTANOL OCTANOL OCTANOL HEXANE OCTANOL HEXANE CYCLOHEXANE HEXANE OLEYL ALCOHOL OLEYL ALCOHOL 01-I-PR. KETONE 01- I-PR. KETONE HEXANE OCTANOL OCTANOL OCTANOL CYCLOHEXANE OLEYL ALCOHOL CHCL~ OCTANOL BENZENE N-BUTANOL TOLUENE TOLUENE PRIM. PENTANOLS S-PENTANOLS TETRAL I N BRCMOFORM OCTANOL OLEYL ALCOHOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OLEYL ALCOHOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OILS HEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL HEXANE OCTANOL D I ETHYL EWER DIETHYL ETFER CYCLOHEXANE OILS OCTANOL OCTANOL CYCLOHEXANE HETH. OECANOATE OLEYL ALCOHOL OCTANOL CYCLOHEXANE METH. OECANOATE OLEYL ALCOHOL OCTANOL CYCLOHEXANE OLEYL ALCOHOL OCTANOL OCTANOL CHCL~ OCTANOL OCTANOL CYCLOHEXANE HETh. OECANOATE OLEYL ALCOHOL OCTANOL OCTANOL CYCLOHEXANE METI". DECANOATE OLEYL ALCOHOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE METH. OECANOATE OLEYL ALCOHOL OCTANOL OCTANOL OCTANOL CHCL3 OCTANOL
REF FOOT NOTE 298 56 206 299 299
LOGP SOLV 3.22 2.22 4.17 0.18
LOGP OCT 3.22 2.22 5.01
EMPIRICAL FORMULA
NAME
= = =
27
.56 4 9
300
299 300 300 93 93 299
5.01
2.15 -0.52 -0.30 2.37 2.09 -1.48 -1.62 -1.30 3.72 3.06 3.69 -0.15 .1.98 1.20 2.03 1.69 0.96 0.88 1.71 1.85 0.82 2.04 0.04 2.64 2.01 2.39 2.46 2.24 2.41 2.41 3.38 3.38 3.39 2.54 -0.84 -1.31 1.49 1.49 1.58 1.46 1.49 1.51 1.54 1.35 1.75 1.75 1.25 1.18 2.32 2.36 -0.13 1.95 -2.60 0.20 -0.49 -0.51 -0.39 0.27 2.99 2.63 -0.52 2.12 2.02 2.35 0.26 1.48 1.36 2.59 -0.09 2.23 2.84 1.91 0.03 2.50 2.47 -0.70 1.96 1.76 2.15 2.19 0.08 1.34 1.23 2.39 2.44 -0.70 -0.26 2.18 2.02 2.78 2.69 1.44 0.52 2.27
2.91 2.64
46 46
56
9 56 300 300 47 218 33 253 42 36 182 195 246 47
3.72 3.06 3.69 2.53 2.31 2.03 3.02 0.82 2.35 2.01 0.63 2.64 2.56 2.39 2.46 2.24 2.41 2.41 3.38 3.38 3.39
=
=
=
A
=
A
A
12 36 12 12
3.08 A
10
124 10 10 301 301 301 301 301 301 124 283 2 83 10 301 301 10 301 218 302 173 299 186 218 186 218 218 218 218 206 299 238
=
= =
= = =
= = =
3.08
-0.84 -1.31 1.49 1.49 1.58 1.46 1.49 1.51 1.54 .2.38 1.75 1.75 1.25 1.18 2.32 2.36 -0.13 0.20 0.39 0.40 0.69 2.99 2.63 2.59 2.57 2.35 1.93 1.91 2.59 2.77 2.84 1.91 1.21 2.50 2.47 2.43 2.31 2.15 2.19 1.79 1.78 2.39 2.44 2.65 2.57 2.78 2.69 1.44 1.64 2.27
73 71
= =
= =
= = =
= =
A
12
0.55
=
=
=
= = =
27
=
8 8
B
3
303 304 305 10 10 124 124 124 10 124 124 124 10 56 ,124 10 217 217 10 301 124 124 124 10 301 124 124 124 10 301 124 56 124 124 2 68 268 217 217 10
= =
07 07
= =
A
=
=
= =
07 07
= = =
A
C5H14SI 1 C6F6 C6HlCL4N3 C C6H 1 L4N3 CbHlCL501 CbHlCL501 CbHlF5Ol CbHlF501 CbHlF501 CbH2F401 CbH2KlN307 CbH2N3NA107 CbH3CLlN402 CbH3CL301 C6H3CL301 CbH3CL301 C6H3F301 CbH3F30 1 CbH3N301 CbH3N307 C6H3N307 CbH3N307 C6H3N307 CbH3N307 C6H3N307 C6H3 N3 0 7 CbH3N307 CbH3N307 C6H4BRlN102 CbH4BR201 CbH4CLlN102 CbH4CLlN102 C6H4CLlN102 CbH4CL1N l O 2 C6H4CLlN102 C6H4CL2 C6H4CL2 CbH4CL2 C6H4 I 2 0 1 CbH4NlNA103 C6H4N1NA103 CbH4N204 C6H4N204 C6H4N204 CbH4N204 C6H4NZ04 C6H4N205 C bH4N2 0 5 CbH4N205 C6H4N205 C6H4N205 CbH4N205 C6H4NZ05 CbH4N205 C6H4N205 C6H4N205 C6H4N4 C6H4N402 C6H4N402 C6H402 C6H402 C6H402 C6H402 ~ 6 ~ 4 0 2 C6H58R1 CbH5BR101 C6H58RlOl CbH58R101 CbH58R101 C 6H5 BR 1 0 1 C6H5BR101 C6H5BR101 C 6H 58R 1 0 1 C6H58R101 C6H58R101 C6H58R101 C6H5CL1 CbH5CLlN20451 C6H5CLlNZ0451 C6H5CL 1 0 1 CbH5CL101 C6H5CL101 C6H5CL101 C6H5CL 1 0 1 C6H5CL101 C6H5CL101 C6H5CL101 C6H5CL101 CbH5CL 1 0 1 C6H5CL101 C6H5CL101 C6H5CL101 C6H5CL101 C6H5CLlO1 C6H5CL101 Cbh5CL2Nl C6H5CL2N1 C6H5CLZN102Sl CbH5CLZN10251 CbH5F1
SI LANE, OIMETHYL-PROPYL HEXAFLUOROBENLENE 4 r 5r 6.7-TETRACHLOROBENZOTR IAZOLE 4 1 51 6 r 7-TETRACHLOROBENZOTR IAZOLE PENTACHLOROPhENOL PENTACHLOROPHENOL PENTAFLJOROPHENOL PENTAFLUOROPnENOL PENTAFLJOROPHENOL TETRAFLUOROPHENOL POTASSIUM P I C R A l E S O D I U M PICRATE 5-CHLORO-4-hITROBEhZOTRIAZOlE 214r5-TRICHLOROPHEhJL 21 4.6-TRICHLOROPHENOL 29 496-TRIChLOROPHEh9L TR IFLUOROPHENOL TRIFLUOROPHENOL 2 ~ 4 r b - T R I N I T R O P H E N O L / P I C R I C ACID/ ~ I ~ ~ ~ - T R I N I T R O P H E N O L / P I CACID/ RIC ~ I ~ v ~ - T R I N I T R O P H E N O LP I C R I C ACID/ / 2 ~ 4 r 6 - T R I N I T R O P H E N O L f P I C R I C ACID/ 2r4r6-TRINITROPHENOL/PICRIC ACID/ 21 4 ~ 6 - T R I N I T R O P H E N O L / P I C R I C ACID/ 2r4,b-TRINITROPHENOL / P I C R I C ACID/ ~I~~~-TRINITROPHENOL/PICRIC ACID/ 21 49 6-TRINITROPHENOLIP I C R I C ACID/ 2 ~ 4 r 6 - T R I N I T R O P H E N O L f P I C R I C ACID/ BENZENE+ 3-BROMO- 1-NITRO 29 4-018ROHOPHENOL BENZENEI 4-CHLORO- 1-NITRO BENZENE I 3-CHLO RO-1-N I TRO BEhZEhEv 2-CHLJRO-1-VITRO
8EhZEhE~3-CnL09C-l-NITRO
BEhZE\E~4-CHLORO-l-YITRO
M-OICttLOR38ENZENE C-OICHLOROBE\ZENE P-OlCnL3ROaEhZENE 21 4-01-IOOOPHENOL SOOIUq P-hITR3PHEhOXIOE S O O I J H P-\ITROPhEk3XIOE IPKA 7-15] M-OINITRO8ENZENE M-OINITRJBEhZEkE 0-DINITROBEhZEhE P - 0 1 h I T R O a E h LENE P- 01h I T R O B E h Z E h E 2.4-OIhlTROPHEhCL 214-SIhITROPnENOL 2~4-DlhITROPttE%OL 2,4-OIhITR3PHEhOL 2~5-OIhITR3PHENOL 215-0lhlTR0PHEN0L 216-01hITR0PhEN0L 2,6-SlhITROPt?EhOL 3t5-OIhITROPdENOL 3r 5-OIhITROPnEhOL ISOPROPEVVLAMIhEt 1 ~ 1 s 3 - T R I C Y A h O 5 - N I TRO8ENZTR I AZOL E 5-hlTRSBEhZTRIAZOL E PJ INOhE W INONE W IhONE QJINOhE PUIhJhE 8ROMOBENZEhE M-8ROYOPkEhOL H-8ROHOPnENJL M-8ROHOPnEVOL M-8ROMSPnEhOL 0-BROHOPnE\OL 0-BROHOPtt EVOL 0- BROYCPHENOL O-BROYJPnE\OL P-dROYOPhENOL P-BROHOPkEYOL P-aROHOPnEWL CHLOROBENZEhE 3-\1TRC-4-CrlLORO8ENZE'4ESULFONAMlOE
3-hITRO-4-CHLOROBENZEVESULFOhAYIDE H- C ~ L O JPHEhJL r7
M-CHLOROPHEhOL M-CttLlR3PHi\OL M-CnLOR3PHEhOL M-CHL3ROPHEhOL 0-CnLOROPdEIOL 0-CHLOROPHENOL 0-CHLOROPHENOL 0-CHLaROPHENOL 0-CHLOROPHENOL P-CHLOROPHENOL P-CHLOROPHENOL P-CHLOROPHENOL P-CHLO ROPHENOL P-CHLOROPHENOL P-CHLOROPHENOL 2 , 3-OIChLOROA\ILINE 3,4-0ICHLOROA\ I L 1 I E 3 - 4 - 0 1 CnLOR78EhZEhESULFOhAMIOE 3 - 4 - 0 1 CHLOROBENZENESULFONAHIOE FLUOROBENZENE
~~~ ~ ~ ~
partition Coefficients and Their Uses
NO. 1401 1402 1403 1404 1405 1406 14C7 1408 1409 1410 1411 1412 1413 1414 1415 1416 1417 1418 1419 1420 1421 1422 1423 1424 1425 1426 1427 1428 1429 1430 1431 1432 1433 1434 i435 1436 1437 1438 1439 1440 1441 1442 1443 1444 1445 1446 1447 1448 1449 1450 1451 1452 1453 1454 1455 1456 1457 1458 1459 1460 1461 1462 14.53 1464 1465 1466 1467 1468 1469 1470 1471 1412 1473 1474 1475 1476 1477 1478 1479 1480 1481 1482 1483 i4e4 1485 1486 1487 1488 1489 1490 1491 1492 1493 1494 1495 1496 1497 1498 1499 1500
SOLVENT OCTPNOL CYCLOHEXANE CYCLOHEXANE METH. OECANOATE OLEYL ALCOHOL OLEYL ALCOHOL OCTANOL CYCLOHEXANE CYCLOHEXANE METH. OECANOATE OLEYL ALCOHOL OLEYL ALCOHOL OCTANOL CYCLOHEXANE OLEYL ALCOI'OL OLEYL ALCOHOL OCTANOL OCTANOL CYCLOHEXANE METH. OECANOATE OLEYL ALCOHOL OCTANOL OLEYL ALCOHOL OCTANOL CYCLOHEXANE CYCLOHEXANE OLEYL ALCOHOL OCTANOL DIETHYL ETHER ETHYL ACETATE CLCHZCHZCL OCTANOL OCTANOL DIETHYL ETHER CHCL~ OlETHYL ETHER CHCL3 OCTANOL OCTANOL CYCLOHEXANE OCTANOL OCTANOL DIETHYL ETHER DIETHYL ETHER CYCLOHEXANE CHCL3 BENZENE I-BUTANOL CLCHZCHZCL OCTANOL OCTANOL DIETHYL ETHER CYCLOHEXANE CHCL3 BENZENE I-BUTANOL XYLENE TOLUENE CCL4 CS2 OCTANOL OCTANOL DIETHYL ETI'ER DIETHYL ETHER CYCLOHEXANE CYCLOHEXANE CHCL3 CHCL3 BENZENE BENZENE I-BUTANOL CCL4 CCL4 CLCHZCHZCL HEXANE CS2 CYCLOHEXANE DIETHYL ETHER CHCL3 OCTANOL OIETHYL ETHER CHCL3 OCTANOL OCTANOL OCTANOL OILS N-HEPTANE BENZENE BENZENE BENZENE BENZENE BENZENE OCTANOL BENZENE OCTANOL OCTANOL BENZENE BENZENE OCTANOL CHCL3
~~
REF FOOT NOTE 10 124
LOGP SOLV 1.93 -1.00 -0.70 1.56 1.43 1.73 1.71 -0.70 -0.15 1.00
LOGP OCT 1.93 2.02 1.98 2.28 1.71 1.41 1.46 1.95 1.77 2.04 2.03 3.25 2.93 2.89 2.77 2.65 2.34 2.91 3.13 -1.61 -1.46 -1.00 2.01 1.99 -0.97 -0.27 0.03 -0.65 1.85 1.88 2.00 2.00 2.05 2.02 1.59 1.77 2.01 1.79 1.73 2.03 1.97 2.16 1.75 3.58
EMPIRICAL FOR MU L A
NAME M-FLUOROPHENOL M-FLUOROPHENOL M-FLUOROPHENOL M-FLUOROPHENOL M- FLUOROP HENOL M-FLUOROPHENOL 0-FLUOROPHENOL 0-FLUOROPHENOL 0-FLUOROPHENOL 0-FLUOROPHENOL 0-FLUOROPHENOL 0-FLUOROPHENOL P-FLUOROPHENOL P-FLUOROPHENOL P-FLUOROPHENOL P-FLJOROPHEhOL IOWBENZEkE M- IOWPIIENOL n- IOOOPHENOL M-1000PHENOL M- 1000PHENOL 0- 1000PHENOL 0- IOWPHENOL P-1000PHENOL P- 1000PHENOL P-1000PHENOL P- IODOPHENOL 1000XY BENZENE P-IOOOBENZENESULFONIC ACID 0 P- I O 00 @ EN Z EN E S UL FON I C A C I P-IOOOBENZENESULFONIC AC I O NITROSOBENZENE NITROSOBENZENE 2-CARBOXYPYRIOINE/PICOLINIC
300
124 124 300 10 124
300
124 124 300
0.90
1.39 1.77
10
300
124 300 56 10 124 124 124 10 124 10 124 56 124 56 306
-1.00
1.49 1.48 3.25 2.93 -0.10 2.41 2.23 2.65 1.79 2.91 0.00 0.21 2.59 26
=
=
= =
-1.61
-1.82
=
A
306 306
56 65 112 112 112 112 10 30 1 141 10 301 12 12 50 12
-0.96
-2.52 2.01 1.99 -2.05 -1.64 -0.99 -2.05 1.85 1.88 1.46 2.00 2.00 2.20 2.18 -1.52 0.41 0.38 1.79
=
=
B A 8 A
= = =
=
A A
3
112 248 307 248 4 248 10 301
A A
0.93
1.79 1.73 2.18 1.49 2.54 2.33 1.60 2.30 2.28 2.07 2.17 1.91 1.91 2.04 2.01 -1.93 -1.79
=
A
=
8 B
A
3
308 307
308
4 308
308
308 308 10 301 3 112 30 8 248 307 308
1.91 = 1.91 = 1-90 A 1.89 A 1.29 1.46 1.56 1.48 1.97
0.08
0.27 0.15 0.07 1.76 -0.99 -1.06 0.79 -2.22 -1.04 1.01 12
308
248 4 308 234 2 48 308 308 141 112 112 186 112 112
A A A
-1.08
0.03
1.34 0.58 -0.05 2.13
10
309
15 .6
2.15 2.22 2.26
301
173
-0.82 1.25 1.34 1.38 0.53 2.13 1.56 2.15 2.28
=
B
N
= = =
B
C6H5F101 C6H5FlO 1 C6H5F101 C6H5F101 C6H5F 1 0 1 C6H5F101 C6H5FlO1 C6H5F 10 1 C6H5F101 C6H5F101 C6H5F101 C6H5F 1 0 1 C6H5F101 C6H5F 101 C6H5F101 C6H5F101 C6H511 C6H51101 C6H51101 C6H5I 1 0 1 C6H5 110 1 C6H51101 C6H51101 C6H5 I1 0 1 C6H51101 C6H5 I101 C 6 H 5 I 101 C6H51101 C6H5110351 CbH51103Sl C6H51103S1 C6H5NlOl C6H5N101 C6H5N102 C6H5N102 C6H5N102 C6H5N102 CbH5N102 C6H5N102 C6H5N102S1 CbH5N103 C6H5N 103 C6H5N103 C6H5N103 C6H5N103 C6H5Nl03 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5 N1 0 3 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N 1 0 3 C6H5NlO3 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 CbHSN103 C6H5N103 C6HS N1 0 3 C6H5Nl03 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N103 C6H5N3 C6HSN3 C6H5N3 C6H6 C6H6 C6H6
C .H b 6 . .
ACID/
2 - C A R 8 O X Y P Y R I O I N E / P I C O L I N I C ACID/ 3-CAR8OXYPYRIOINE/NICOTINIC ACID/

3 - C A R 8 O X Y P Y R I O I N E / N I C O T I N I C ACID/ NITROBENZENE NITROBENZENE 2-(8-NITROVINYL) THIOPHENE M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL M-NITROPHENOL 0-NITROPHENOL 0-NITROPHENOL 0-NITROPHENOL 0-NITROPHENOL 0-NITROPHENOL 0-NITROPHENOL 0-NITROPHENOL C-NITROPHENOL 0-NITROPHENOL 0-N I T R O PHENOL 0-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NI TROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL P-NITROPHEUOL P-NITROPHENOL P-NITROPHENOL P-NITROPHENOL 2-(8-NITROVINYL) FURAN PI COL IN I A C I N-o x I OE c 0, P I COLIN I C ACID .N-0 X I DE BENZOTRIAZOL E AZOLE BENZOTR I AZOLE BENZOTR I BENZENE BENZENE BENZENE BENZENE BE NZ ENE PHENYLBORON I C AC IO. 4-BROMO PHENYLBORONIC AC 1 0 1 4-CHLORO PHENYLBORONIC ACIDIC-FLUOR0 PHENYLBORONIC ACIO+3-NITRO PHENYL BORON I C A 10.2-N ITRO C H-BROMOANIL INE W- BRfflOANIL INE 0-BROMOANIL I N E P-BROHOANIL I N P-BROHOANIL I N P-BROMOANILINE P- BROMOBENLENESUL FONAH IOE P-BROMO8ENLENESULFONAHIOE
3 10
311 311 311 311
311
312 313 312 312 313 72 217 217
6 6 6 6 6
01 .0
-0.09 -0.51 -1.09 -0.82 2.10 2.20 2.29 2.26 2.06 2.12 1.36 0.39
07 07
2.10 2.07 2.29 2.26 1.98 2.09 1.36 0.92
-B
B
B
=
N
C6H6 C6H6BlBR102 C6H6BlCL102 C6H681F102 C6H681N104 C6H6BlN104 C6H6BRlN1 C6H6BRlNl C6H6BRlNl CbH6BRlNl C6H6BRlNl CbHbBRlN1 C6H69RlN102Sl CIHIBRlNlOZSl

NO. 1501 15CZ 1503 1504 1505 1506 15C7 1508 15C9 15 10 1511 1512 1513 1514 1515 15 16 1517 15 18 1519 1520 1521 1522 1523 1524 1525 1526 1527 1528 1529 1530 1531 1532 1533 1534 1535 1536 1537 1538 1539 1540 1541 1542 1543 1544 1545 1546 1547 1548 1549 1550 1551 1552 1553 1554 1555 1556 1557 1558 1559 1560 1561 1562 1563 1564 1565 1566 1567 1568 1569 1570 1571 1572 1573 1574 1575 1576 1577 1578 1579 1580 1581 1582 1513 1584 1585 1586 15-87 1588 1589 1590 1591 1592 1593 1594 1595 1596 1597 1598 1599 1600 SOLVENT REF FOOT NOTE LOGP SOLV 1.88 1.90 0.89 1.93 1.94 1.37 0.71 0.64 1.90 1.92 1.25 LOGP OCT 1.88 1.90 1.88 1.91 EMPI R l C AL FORMULA NAME
0 C T ANOL OCTANOL CYCLOHEXANE BENZENE BENZENE CCL4 N-HEPTANE HEX AOEC AN E OC TANOL OCTANOL CYCLOHEXANE BENZENE BENZENE CCL4 N-HEPTANE HEXANE OCTANE HEX AOEC AN E DECANE OCTANOL CYCLOHEXANE BENZENE BENZENE BENZENE BENZENE CCL4 01-PENTYL ETHER N-HEPTANE N-I-EPTANE N-HEPTANE PARAFFINS HEXAOECANE OCTANOL CHCL3 OCTANOL CHCL3 OCTANOL CHCL3 HEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL DIETHYL TI-ER CHCL 3 CHCL3 OCTANOL OCTANOL DIETHYL TI-ER CYCLOHEXANE CYCLOHEXANE CHCL3 CHCL3 BENZENE BENZENE BENZENE TOLUENE CCL4 CCL4 N-HEPTANE N-HEPTANE N-HEPTANE OCTANE CSZ OCTANOL OC T ANOL OCTANOL 0 1 ETHYL ETHER CYCLOHEXANE CYCLOHEXANE CHCL3 BENZENE BENZENE TOLUENE CCL4 CCL4 N-HEPTAN E N-HEPTANE HEXANE OLEYL ALCOHOL cs2 OCTANOL OIETHVL ETHER CYCLOHEXANE CYCLOHEXANE CHCL3 C HCL 3 BENZENE BENZENE BENZENE TOLUENE CCL4 CCL4 N-HEPTANE N-HEPTANE N-HEPTANE OCTANE
10
301 314
= =
8
8
313
315 314 314 314
268
301 314 314 315 314 3 14 3 14 3 14 314 3 14 301 314 314
.90 .92
=
=
2.13
2.08 1.73 1.12 1.11 1.03 1.07 1.12 1.83
.02 8 -99 B
.83 = 1.81 1.80 1.87 1.80
06 .9
1.82 1.81 1.91 1.80
313
72 315 314 315 75 3 14 315
8 8 B
13 .1
0.64
06 .3
0.57 0.64 0.50 0.56 1.29
316 3 14
217 217 217 217 217 217 317 312 10 3 12 10 312 3 12 3 12 112 112 318 10
07
07 07 07 07 07
02 .6
0.74 0.46 0.84 0.14 3.24 1.30
1.29 0.89 0.74 0.96 0.84 0.69 1.30 1.30 1.26 1.15 2.98 3.34 3.34
=
N
1.30
= = = =
=
8
= =
12 .6
12 12 1.15 2.98 3.34 3.34 -1.72 -1.37 -1.22 1.37 1.37 1.71 -0.42 -0.42 1.61 1.59 1.31 1.30 1.36 1.19 0.45 0.43 -0.57
-0.61
-1.40 -1.27 1.31 1.37 1.61 1.13 1.12 1.46 1.45 1.49 1.49 1.39
8 8
301
112 319 314 112 2 54 319 314 72 319 319 314 319 2 54 314 314 319 312 186 301 112 319 314 112 319 72 319 319 314 3 19 315 319 82 319 10
= =
A
8
8 8 8
B
8 N
-0.62
-0.56 -0.61 0.52 1.44 1-03 1.79 1.95
1.44
18 .3
1.79 1.83 1.60 1.79 1.81 1.84 2.25
= = =
A B
50
03 .6
-0.70 2.13 1.78 1.81 1.64 1.08 1.08 0.25 0.25 0.21 1.15 1.14 1.39 1.48 -1.00 -1.00 1.23
B
8 8 N
1.71 1.39 1.41 0.78 0.89 1.19 1.19 1.21 1.19 0.61
=
A
112 3 19 3 14
112
254 3 19
314 72 319 319 314 319 254 3 14 314
13 .0
0.92 6.93 0.95 0.78 -0.13 -0.14 -1.14 -0.89 -1.13
B B
8
B
8
B
N
-1.25
C6H6CL l N 1 C6H6CL 1N 1 C6H6CLlNl C6H6CL 1N1 C6H6CLlNl C6H6CLlNl C6H6CLlNl CbHbCLlNl C6HbCLlN 1 CbHbCLlNl C6H6C L 1N1 C6H6CLlN1 C6H6CLlNl C6H6CL 1N1 C6H6CL 1N1 C6H6CL1 N1 C6H6CL 1 N 1 C6H6CL1 N1 CIHbCLlNl C6H6CL 1N1 C6H6CL1 N1 C6H6CLlNl C6H6CLlNl C6H6CLlNI C6H6CL1 N1 C6HbCLlNl C6H6CLlNl C6H6CLlNl C6H6CL1 N1 C6H6CLlN1 C6H6CL1 N1 C6H6CLlNl C6H6CLlN10251 C6H6CLlN102Sl C6H6C L 1N 1 0 2 5 1 C6H6CLlN102Sl C6H6CLlN102Sl C6H6CLlN10251 C6H6CL6 C6H6F1 N1 C6H6FlNl C6H6FlNl C6H6FlNl C6H6 I1 N 1 C6H6 1 1 N 1 C6H6I 1 N 1 C6H6N201 C6H6NZOl C6H6N201 C6H6N202 C6H6NZO2 C6H6N202 C6H6N202 C6H6N202 CbH6N.202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 CbH6NZ02 C6H6N202 CbH6N202 C6H6N202 C6H6N202 C6HbN202 C6H6N202 C6H6N202 CbH6NZ02 C6HbN.202 C6H6NZ02 C6H6N202 C6H6NZ02 C6H6N202 C6H6N202 C6H6NZ02 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6NZ02 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6H6N202 C6HbNZ02 C6H6NZ02 C6H6N202
W-CHLOROANILINE M-CHLOROANIL I N E M-CHLOROANILINE M-CHLOROANIL INE M-CHLOROANIL INE M-CHLOROANILINE M-CHLOROANIL I N E H-CHLO ROAN1L I N E 0-CHLOROANILINE 0-CHLOROANIL I N E 0-CHLOROANIL INE 0-CHLOROANIL I N 0-CHIOROANIL IN E 0-CHLOROANIL I N E 0-CHLOROANIL I Y E 0-CrlLOROAhlL INE 0- CHLOROANIL INE 0-CHLOROAQIL INE 0-CHLO R O A h I L I N E P-CHLOROANIL I N P-CHLOROANIL INE P-CHLOROAtvILIhE P-CHLOROAQILINE P-CHLOROANILINE P-CHLORJANIL INE P-CHLOROAhlL I h E P-CnLOR3ANIL INE P-CHLOROANIL INE P-CHLOROANIL I N E P-CHLOROANIL INE P-ChL3ROANIL I N E P-CHLJROAN IL I N E W-CHLOROBEYZENESULFONA~IOE M-ChLJROBENZEN ESUL FOk AM I O E 0-CHLOROBEhZENESULFJNAMIOE O-CHLORO8E"iZENESUL FOkAMI DE P- CHLO 40 BEN 2 EN ESUL F3hAM 1OE P-CHLOROBEhLEVESUL F JhA'4IOE
l v 2 ~ 3 * 4 , 5 ~ 6 - H E X A C H L O R O C Y C L O d E X A N E/ L I h 3 A h E / M- FLUOROANI L I t v E
M-FLUOROANIL INE 0-FLUOROANIL INE P-FLUOROANIL INE M-1000ANIL I N 0-IOOOANIL I N E P-1000ANIL I N I-NICOT INAMIOE M-NITROANILINE H-hlTROAhIL INE M-NITROANILINE M-NITROANIL INE M-NITROANILINE M-NITROANILINE H-NITROANILINE M-NITROANILINE M-NITROANIL INE M-NITROANILINE M-NITROANIL INE M-NITROANIL INE W-NITROANILINE M- NITRO AN I I NE L M-NITROANILINE L M-NI TRO AN I 1NE W-NITROANIL INE M-NITROANILINE 0- NITRO AN I I NE L 0-NITROANIL I N E 0-NITROANILINE 0-NITROANILINE O-NITROANIL INE 0-NITROANILINE 0-NITROANILINE 0-NITROANIL I N 0-NITROANILINE 0-NITROANIL I N E 0-NITROANIL I N 0-NITROANILINE 0- NITRO AN I L I N E O-NITROANIL I N 0-NITROANIL I N E 0 - N I TRO AN I L I NE 0-NITROANIL I N E P-NITROANILINE P-NITROANILINE P-NITROANIL INE P-NITROANILINE P-NITROANILINE P-NITROANIL INE P- N I T RO AN I I L NE P-NITROANILINE P-NITROANILINE P-NITROANIL I N P-NITROANILINE P-NITROANIL I N E P-NITROANIL I N E P-NITROANILINE P-NITROANILINE P-NITROANIL I N

REF FOOT NOTE LOGP OCT EMPIRICAL FORMULA C6H6NZ02 CbHbN202 CbHbN202 C6H6N202 CbH6N202 CbHbN202 C6H6N202 CbHbNZO4Sl CbHbN204Sl C6H6N204S1 CbHbN20451 tbH6N204Sl CbH6N204S1 CbHbN2Sl CbHbN251 CbHbN4Sl C6HbOl C6Hb01 CbHb01 CbH601 C6HbO1 C6H601 C6H601 C6H601 C6H601 C6H601 C6H601 C6HbOl C6H601 C6H601 C6H601 C6H601 C6H601 C6HbOL C6H601 C6H601 C6H6Ol C6H601 C6H601 CbH601 C6H601 CbHbOl C6Hb01 C6H601 C6HbOl C6H601 C6H601 C6H601 C6H601 C6H601 C6H601 C6H601 C6H601 CbH601 C6H601 C6H601 C6H601 C6H601 C6H601 C6HbOl C6H601 CbH601 CbH601 C6H601 C6H6Ol CbHbO2 C6H602 C6Hb02 C6H602 C6H602 C6H602 C6Hb02 C6Hb02 C6H602 C6H602 CbH602 C6H602 C6Hb02 C6H602 C6H602 CbH602 CbHbO2 C6H602 C6H602 C6H6Q2 CbH602 CbH602 C6H602 C6H602 CbH602 C6H602 C6H603 C6H603 ~ 6 ~ 6 0 3 C6H603 C6H603 CbH603 C6H603 t6Hb63S1 C6H606 NAME
NO.
SOLVENT
LOGP SOLV
1601
1602 1603 1604 1605 1606 16C7 1608 1609 1610 1611 1612 1613 1614 1615 1616 1617 1618 1619 1620 1621 1622 1623 1624 1625 1626 1627 1628 1629 1630 1631 1632 1633 1634 1635 1636 1637 1638 1639 1640 1641 1642 1643 1644 1645 1646 1647 1640 1649 1650 1651 1652 1653 1654 1655 16 56 1657 1658 1659 1660 1661 16t2 16t3 1664 1665 16 66 1667 1668 1669 1670 1671 1672 1673 1674 1675 1676 1677 1678 1679 1680 1681 1682 1683 1684 1685 l6eb 1687 1688 1689 1690 1691 1692 l6S3 1694 1695 1696 16S7 1698 1699 1700
csz
CS2 OIETHYL ETkER CHCL3 ETHVL ACETATE CCL4 N-BUTYL ACETATE OCTANOL CHCL3 OCTANOL CHCL3 OCTANOL CHCL3 DIETHYL ETHER CHCL3 CHCL3 OCTANOL OCTANOL 01 ETHVL ETFER 01 ETHVL ETPER CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 CHCL3 CHCL3 CHCL3 OILS OILS OILS OILS BENZENE BENZENE BENZENE BENZENE BENZENE BENZENE BENZENE XYLENE XYLENE TOLUENE TOLUENE TOLUENE NITROBENZENE NITROBENZENE PRIM. PENTANOLS PRIM. PENTANOLS N-BUTYL A C E T A T E CCL4 CCL4 CCL4 HETH. OECANOATE ETHER 01-I-PR. N-HEPTANE N- I-E PT AN E HEXANE HEXANOL OLEYL ALCOHOL OLEYL ALCOHOL cs2 PARAFFINS BROMOFORM OCTANOL OCTANOL DIETHYL ETI-ER DIETHYL TI-ER BENZENE N-BUTYL ACETATE CLCHZCHZCL OCTANOL OCT ANOL DIETHYL ETI-ER OIETHYL E T H E R 01 ETHYL ETPER BENZENE CL CH2CH2CL 01-BUTYL ETI'ER 01-I-PR. ETHER OCTANOL OCTANOL 0 1 ETHYL ETHER DIETHYL ETI-ER OIETHYL E T H E R DIETHYL E T H E R OILS BENZENE CLcr2CH2cL 01-I-PR. ETHER CHCL3 BENZENE ETHYL A C E T A T E DIETHYL E T P E R DIETHYL ETkER DIETHYL ETI-ER D l ETHYL E T H E R 01 ETHYL E l l - E R DIETHYL ETFER
319 3 14 320 321 321 320 3 20 217 217 217 217 217 217 112 112 322 10 301 3 323 124 132 324 325 56 300 243 324 326 2 54 324 173 224 327 35 324 328 329
0.05 0.05
1.80
2.15 2.45 3.36 2.23 07 07
1.70
2.64 2.58
A N
2.06
0.55 0.85 0.34 0.69 0.64 0.65 0.07 -0.58 -0.39 1.46 1.48 1.55 1.50
0.55
-0.36 0.34 0.14 0.64
=
A
07
07 07 07 12
=
*
A A
N
-0.60
-0.05 -0.41 -0.33 1.46 1.48 1.64 1.58 -1.00 -0.12 -0.93 -0.77 -0.81
B
8
= =
A A
.
45
-1.00 0.00
45 0.34 0.37 0.36 0.81 0.78
0.60
45 0.75 0.36 0.34 0.41 0.40 0.37 0.32 0.42 0.13 0.18 0.22
330
2 19 248 324 42 324 328 42 324 328 182 324 331 324 328 3 29 124 331 310 2 54 324 331 124 300 248 32 7 7 10 301 3 248 248 331 248 56 301 45 45 45
03 .2
0.23 0.95 0.87 1.21 1.50 1.58 -0.42 -0.50 -0.36 1.21 1.12 -0.92 -0.82 -0.96 1.46 1.23 1.19 -0.26 -0.85 0.18 0.80 0.77 0.62 0.67 -2.11 0.32 -1.50 0.88 1.01 1.04 0.86 0.89 -1.19 -0.63 0.11 0.62 0.59 0.50 0.46 0.36 0.37 0.38 -0.83 -2.16 -1.61 -0.13 -0.22 -0.24 0.13 0.23
45
1.22 1.54 1.55 1.49 1.93 1.96 1.76 1.87 1.76 1.70 1.77 1.76 1.73 1.69 1.81 1.93 1.97 1.77 1.86 1.75 1.66 1.60 1.14 1.55 1.58 1.55 1.40 1.55 1.65
A A A A A A A A A A A A A A A A A A A A
A A A
45
1.78 1.75
0.80 0.77 0.67 0.70 0.57 0.88 1.01 1.03 0.87 0.90 0.21 1.27 0.59 0.50
=
A A
12
=
=
A A A A
3 3 32
323 248 248 332 332 302 301 12
= =
A A A A A
P- N I TRO AN I L I N E P-NITROANIL I N E N-NITROSOPHENVLHVOROXVL AMINE N-NITROSOPHENVLHVOROXVL AMINE N-NITROSOPHENVLHVOROXVL AMINE N-NITROSOPHENVLHVOROXYL AMINE N-NITROSOPNENVLHVOROXVLAMINE M-NITROBENZENESULFONAM I O M-NIIROBENZENESULFONAMIOE 0-NITROBENZENESULFON AN I DE 0-NITROBENZENESULFONAMIOE P-NITROBENLENESULFONAMIOE P-NITRO8ENLENESULFONAMIOE PV R I 01 NE, 4 - T H I OC ARBAMVL / 1-N I C 0 1 I NTHIOAM I E I O PYRIDINE, 4 - T H I O C A R B A M V L / I - N I C O T I N T H I O A M I DE/ METHVLTHIOPURINE PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL Pn ENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL PHENOL H - O l H Y O R O X Y 8 E N Z E N E / R E S O R C I NOL/ M-OIHYOROXYBENZENE/RESORCINOL/ M-D I O R O X Y BEN EN E / R E SORC 1NOL/ HY M-OIHYDROXYBENZENE/RESORClNOL/ M-OIHYOROXY8ENZENE/RESORCINOL/ M- 01 H I O R O X Y BENZENE / R E SORC INOL / M-OIHYOROXYBENZENE/RESORClNOL/ O-OIHYOROXY8ENZENE/CATECHOL/ 0-OIHVOROXY BENZENE/CATECHOL/ O-SInVDROXY8EYZEhE/CATEC~L/ 0-3InYJaOXYBENZEhE /CATECHOL/ 0-OIhY DROXYBE~ZEhE/CATECnOL/ ~. ~. 0-OlUY C R O X Y BEYZEhE/CATECUOL/ 0-31nYO90XYBE~ZE~E/CATEC~oL/ 0-01 nYOROXY8EhZEhE I C A TECHOL / 0-OlrlY D R O X Y BEN ZEhE /CATECHOL/ P-OlflYOR3XYBENZENE/riYOROOUI~~NE/
P-OIrlYOROXY8EhZENE/riYOROOUIhONE/ P-DIrlYOROXYBEhLEQE IHYOROPJIh04E/ P-OI~YORQXI8EYLEhE/~YOR~OUlNONE/ P-OIHYO?OXY8EhLEhE /HYOROOUlNOYE/ P-31 rlYOROXY8ENZEhE/rlVOROPU INDNE / P-OIHYOROXYBEhZEhE IHYDRCOUlh3NE/
P-OIrlYCROXY8ENZEhE/riYOROOUlhO~E/ P-OlHYCROXY8E~ZEhE/HYD~OOUl~OYE/ P-OIUYOROXYBENZEhE/HYORO!?JlhONE/
3
333 3 34 248 305 2 48 248 335 3 36 3 36 336 3 248
0.51
0.44 0.45 0.44 -0.48 0.39 0.40 1.04 0.12 0.32 0.19 -0.19 -0.19 -2.25 -0.15
12
12
N A A A A
A
0.09
-0.35 -0.35 -2.70 -0.30
3
248
2-FURALDEHYDE, rlYORDXYMETHYL 2-FURALDEHYDE, rlVORDXYMETUVL 2-FURALOEHYOE. 5-kYDROXYMETrlYL l r 21 3 - T R l r I Y O R O X Y B E h Z E 4 E / P Y R O G A L L O L / l r 2 t 3-TRIHYOROXV8EhZEhE/PYROG4LLOL/

1~3~5-TRI~VOROXY8EVZENE/PrlLOR~GLUClNOL/ 1~3r5-TRlUYOROXY8EhZEhE/P~LOROGL~lhOL/ BEhZE4ESULFOhlC A C I J AC04ITIC A C I D
3
3
A A

NO. 1701 1702 1703 1704 17C5 1706 17C7 1708 1709 1 7 10 1711 1712 1713 1714 1715 1716 1717 1718 1719 1720 1721 1722 1723 1724 1725 1726 1727 1728 1729 1730 1731 1732 1733 1734 1735 1736 1737 1738 1739 1740 1741 1742 1743 1744 1745 1746 1747 1748 1749 17 50 1751 1752 1753 1 7 54 1755 17 56 1757 1758 1759 1760 1761 17t2 1763 1764 1765 1766 1767 1768 1769 1770 1771 1772 1773 1774 1775 1776 1777 1778 1779 1780 1781 1782 1783 1784 1785 1786 1787 1788 1789 1790 1791 1792 1793 1794 1755 1796 175 7 1798 1799 1800 SOLVENT DIETHYL ETPER I-BUTANOL ME-I-8UT.K ETONE OCTANOL OCTANOL BEN ZEN BENZENE BENZENE BENZENE OC TANOL OCTANOL 01 ETHYL ETHER CYCLOHEXANE CHCL3 CHCL3 BEN ZEN BENZENE XYLENE TOLUENE CCL4 CLCH2CH2CL N-HEPTANE N-HEPTANE N-HEPTANE N-HEPTANE PARAFFINS CHCL3 CHCL3 CHCL3 OCTANOL OCTANOL OCTANOL OCTANOL OIETHYL ETPER CYCLOHEXANE BENZENE BENZENE CCL4 CLCHZCHZCL N-HEPTANE HEXAOECANE OCTANOL OCTANOL CYCLOHEXANE BENZENE CCL4 N-HEPTANE OCTANOL CYCLOHEXANE BENZENE CCL4 N- H EPT AN E OCTANOL OCT ANOL DIETHYL ETI-ER CHCL3 CHCL3 01 ETHYL ETHER CHCL3 OCTANOL CHCL3 CHCL3 OCTANOL BENZENE BENZENE OCTANOL OCTANOL CYCLOHEXANE BENZENE BENZENE BENZENE BENZENE CCL4 N-tEPTANE OCTANOL DIETHYL ETt-ER CYCLOHEXANE CYCLOHEXANE BENZENE BENZENE BENZENE BENZENE CCL4 CLCk2CH2CL N-HEPTANE CYCLOHEXANE BENZENE BENZENE CCL4 N-PEPTANE OCTANOL OCTANOL OCTANOL OCTPNOL DIETHYL ETHER 01 ETHYL ETt-ER CHCL3 CHCL3 CHCL3 CHCL3 REF FOOT NOTE 207 4 195 235 255 311 311 3 11 311 10 301 329 337 254 338 338 72 46 339 329 248 3 10 2 54 338 340 316 2 80 280 2 80 276 276 10 301 248 3 14 314 248 3 14 248 314 314 56 301 314 314 314 314 LOGP SOLV -0.62 0.49 -0.26 2.52 1.58 -0.80 -2.92 -2.78 -2.65 0.90 0.98 0.85 0.02 1.42 1.23 -0.05 LOGP OCT -0.43 0.18 -0.24 2.52 1.58 EUPIRICAL FORMULA

NAUE ACONITIC ACID ACONITIC ACID ACONITIC ACID THIOPHENOL PHENYLBORONI C ACID PHENYLBORONIC A IO C PHENYL BORON IC A C l 014-HYDROXY PHENYLBORONIC AC IDe3-HYDROXY PHENYL, lr4-D1BORONIC ACIOI,~-NITRO ANILINE ANILINE AN I L I N E ANILINE ANILINE ANXLINE ANILINE ANILINE ANILINE AN I L I N AN I L I N E AN I L I N ANILINE AN I L I N E ANILINE ANILINE ANILINE 2-METHYL P Y R I D I N E / t - P ICOL I N / 3-METHYL PYRIDINE/3-PICOLINE/ 4-METHYL PYRIDINE/4-PICOLINE/ 3-METHYLPYRIOXNE /PKA 5.68/ 6.02/ 4-METHYLPYRIDINE /PKA M-AMINOPHENOL 11-All I NOPHENOL M- AMINOPHENOL M-AMINOPHENOL M-AMINOPHENOL M- AM I NOPHENOL M- AM I NO PHENOL M- AM I NOPHENOL M-AU I NOPHENOL M-AMINOPHENOL 0-AMINOPHENOL 0-AMINOPHENOL 0-AMINOPHENOL 0- AM I NOPHENOL 0-AMINOPHENOL 0-AMINOPHENOL P- AM INOPHENOL P-AMINOPHENOL P- AM I NO PHENOL P- AMINO PHENOL P-AM I N 0 PHENOL BENZENESULFONAM I O 8ENZENESULFONAMlOE BENZENESULFONPMIOE BENZENESULFONAMIOE 8ENZENESULFONAUIDE N-HYDROXY BENZ ENESULFONAMI DE N-HYDROXYBENZENESULFONAMIOE 4-CARBAMYLAMINOPYR I DIN E 6-METHYLAMINOPUR I N E 2-AMINO-6-METHYLTHIOPURINE 2-METHOXYPYRIDINE /PKA 3.28/ PHENYL BORON I C AC I D , 3-AMINO PHENYL I l r 4-OIBORON I C ACID 2-AMINO-5-METHYLPYRIOINE I P K A = 7.221 4.6-OIMETHYLPYRIMIOINE M-PHENYLENEOIAMINE M- PHENYLENE0 I AM I N E M-PHENYLENEOIAMINE M-PHENYLENEDIAMINE M- PHENYL ENEO I AM INE M-PHENYLENEUIAMINE M-PHENYLENEDIAMINE 0-PHENYLENtOlAMINE 0-PHENYLENEOIAHINE 0-PHENYL ENEO IAH INE 0-PHENYLENEDIAMINE 0-PH ENY L EN E D I A M I N E 0-PHENYL ENEO I A M I NE 0-PHENYLENE01 AM I N 0-PHENYLENEDIAMINE 0-PHENYLENEDIAMINE 0-PHENYL ENEOI AM INE 0-PHENYLENEUI A M I N P-PHENYLENEDIAMINE P-PHENYLENEDIAMINE P- PHENYL EN E O 1A M INE P-PHENYLENEDIAMINE P-PHENYLENEDIAMINE PHENYLHYDRAZINE 3-PYA I OYLM ETHYL A M I NE SULF A I L AM IDE N SULFANILAMIDE SULF A 1L A M I DE N SU L F A I L A Y I D E N SULFAN I L A M l DE SULFANILAM1 O E SULF AN I L A M I DE SULFANILAMIDE
= =
6 6
6
0.90 0.98 0.87 0.98 0.82 1.24 0.75 1.30
= =
A B B B
12
44
18 0.89 0.25 1.45 -0.03 0.04 -0.26 0.04 -0.12 1.79 1.89
.o.
1.oo
8 8 1.11 N
1.06 1.20 1.22 0.17 0.15 0.22 0.04 0.08 -0.19
8
= = =
18 .8
1.20 1.22 0.17 0.15 0.11 -3.24 -1.36 -1.32 -2.39 -0.58 -3.37 -3.37 0.62 0.52 -2.37 -0.84 -1.75 -2.51 0.04 -3.44 -1.65 -2.64 -3.55 0.31 0.31 0.30 -0.24 -0.24 0.82 -0.82
=
A A A A
0.62 0.52 0.55 0.37 0.04 -0.24 -0.39 0.31 0.31 0.38 0.34 0.35 0.83 -0.16 -0.50 -0.95 -0.89 1.39 1.02 0.62
=
=
A A
301
3 14 314 3 14 3 14 217 10 113 113 217 113 113 276 3 22 322 276 311 311 276 2 76 314 71 314 72 248 314 314 301 E48 314 248 71 314 72 2 48 314 248 314 314 71 314 314 314 283 341 217 186 342 113 343 113 3 44 2 54
=
A A
07
= =
A N N A N
07
16
16
-0.50
-1.05 -0.95 1.39 -2.32 -2.61 1.02 0.62 -2.44 -0.79 -0.77 -0.75 -0.75 -2.49 -2.60 0.15 -0.06 -1.65 -1.31 -0.28 -0.26 -0.26 -0.26 -0.81 0.44 -1.79 -2.81 -1.17 -1.17 -1.78 -3.00 1.25 -0.10 -0.83 -0.72 -0.72 -0.85 -1.40 -1.63 -1.85 -1.52
=
B B
=
=
B B 6 8
0.00 0.02 0.03 0.03

0.15
=
A
0.08
0.35 0.37 0.37 0.37
43
B B B
-0.26 -0.26 1.25 -0.10 -0.83 -0.72 -0.52 -0.63 -0.70 -0.92 -1.07 -0.79
8
=
60
=
A
A
32
C6H606 CbHbO6 C6Hb06 C6H6S1 CbH78102 CbH7B102 CbH7B103 CbH7B103 CbH782N106 C6H7N1 C6H7N1 C6H7N1 C6H7N1 C6H7N1 C6H7Nl C6H7N1 C6H7N1 C6H7N1 C6H7Nl C6H7N1 C6H7Nl C6H7N1 C6H7N1 CbH7N1 C6H7N1 CbH7N1 C6H7N1 C6H7N1 CLH7N1 C6H7N1 CbH7N1 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 CbH7N101 C6H7N101 CbH7N101 C6H7N101 C6H7N101 C6H7N101 CbH7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N101 C6H7N102S1 C6H7NlOZSl CbH7N10251 CbH7N10251 C6H7N102S1 CbH7N103Sl C6H7N103S1 C6H7N301 C6H7N5 C6H7N551 C6H701 C6H8BlN102 C6H8B204 C6H8N1 C6H8N2 CbH8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8NZ C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8N2 C6H8NZ C6H8N2 C6H8N2 CbH8N2 C6H8N2 .~ C6H8N2 C6H8N2 C6H8N202SI CbH8N2OZSl C6h8h202Sl C6h8k2 3 2 5 1
2 44
N
N
N N

LOGP OCT -0.97 -0.64 -1.85 -0.67 -0.29 0.16 1.94 2.94 0.58 1.70 0.96 -0.65 -0.95 -1.03 -0.93 -0.94 -0.49 -1.72 -1.69 -1.80 -1.79 -1.25 -1.38 -1.27 -1.47 -1.63 -1.51 -1.63
N A A A
NO.
1801 1802
SOLVENT CHCL3 BENZENE I-BUTANOL I-PENT. ACETATE CCL4 OILS OILS OILS OCTANOL OILS ME- I-BU T .KETONE 5-PENTANOL S OIETHVL E T C E R DIETHYL TI-ER ME- I-8UT.KETONE OLEYL A L c O r o L I-BUTANOL OCTANOL DIETHYL ETHER DIETHYL T I - E R 01 ETHVL ETHER I -BUTANOL I-BUTANOL PRIM. PENTANOLS CYCLOHEXANONE 2-BUTANONE ME- I-BUT. K ETONE S-PENTANOL 5 OCTANOL OILS SEC-BUTANOL OCTANE OCTANOL CHCL3 OCTANOL OCTANOL OCTANOL OC T ANOL OCTANOL OILS OCTANOL 50%ETHER+50%OHF CCL4 CHCL3 OIETHVL ETHER OILS OILS OCTANOL OCTANOL DIETHYL TI-ER OIEIHVL ETCER 01 ETHVL ETHER N-BUTANOL I-BUTANOL ETHVL ACETATE CYCLOHEXANONE 2 - 6 UT AN ON E ME-I-8UT.KETONE ME- 1 - B U l .KETONE S-PENTANOL S DIETHYL ETCER I-BUTANOL OILS OILS OILS OILS OILS OILS OILS OILS OILS OILS OILS OILS OILS I-OCTANOL OCTANOL OCTANOL CYCLOHEXANE CHCL3 ETHVL ACETATE DCTANOL OCTANOL I-OCTANOL OILS OCTANOL OCTANOL OCTANOL OILS OILS OILS DIETHYL ETHER I-BUTANOL OCTANOL OCTANOL OCTANOL OCTANOL DIETHYL ETHER OIETHYL ETHER OIETHVL ETHER
REF FOOT NOTE 217 343 130 343 343 345 240 240 346 347 195 195 32 2 12 2 2
LOGP SOLV
EMPIRICAL FORMULA
NAME SU LF AN I L AM 1DE SULFANILAMIDE SULF ANILAMIOE SULFANILAMIOE SULFAN ILAM I D BARBITURIC ACIOtOlMETHVL ISOSORBIDE OINITRATE MANNITOL HEXANITRATE 1-HEXVN-5-ONE SORBIC ACIO SORBIC ACID PROPANE T R I CARBOXYL I C A C I 0 PROPANE T R ICARBOXVL IC AC 1D C PROP AN E TR I C A R BOXVL I C A 10 PROPANE TRICARBOXV-IC ACID PqDPAhE TRICARbDXVcIC ACID PROP A% E T R I CAR8OXVL I C ACID CITRIC A C I D C I T R I C ACID C I T R I C ACID C I T R I C ACIO CITRIC ACIO C I T R I C ACID C I T R I C ACID C I T R I C ACID C I T R I C ACID C I T R I C ACID C I T R I C ACID GFORMYLCVCLOBUTAN ECAR B O X A HI O E 1.3- 5 - T Z I M E T k V L - 4 - N I T R O S O P Y R A Z O L E HISTIDINE 2-I-PROPVL-5-NITROIMIDAZOLE I t 5-dEXAOIEhE CVCLOnEIANEUIOlvE OIOXIME 1M IOALOLEI 21 4 9 5 - T R IMEThVLSULFONYL 3-MERCAPTO-4-AM I h 0 - 6 - I-PR- 1t 2 14-117 I A Z I hE-5-ONE 3-METdID-4-AHIhO-6-ETHVL-l~2~4-TRIAZI~E-5-O~E
-1.69
-2.05 -0.96 -0.44 -2.52 -1.18 1.61 2.69 0.58 0.49 1.10 -0.30 -1.22
1803
1804 1805 1806 18C7 1808 1809 1 8 10 1811 1812 1813 16 14 18 1 5 1816 1817 1618 1819 1820 1821 1822 1823 1824 1825 1826 1827 1828 1829 1830 1831 1832 1833 1834 1835 1836 1837 1838 1839
B
0
=
A
3
207 195 5 4 5
-1.30
-1.00 -1.52 0.01 -1.72 -2.06 -2.18 -2.19 -0.53 -0.62 -0.76 -0.67 -0.48 -1.62 -1.16 -0.70 0.19 -1.68 -1.26 2.45 -0.94 3.75 1.22 0.46 -0.24 0.81 0.30 1.02 0.40 1.42 1.75 -0.35 -1.09 0.04
A A
=
A A A
3
207 213 4 184 48 194 194 195 195 348 284 84 2 56 56 265 206 134 134 349 65 2 58 255 125 3 50 285 2 2 173 255
-0.70
0.95 -2.86 2.45 -0.28
=
B
19
=
N
3.75
1.22 0.46 -0.24 0.81 0.69 1.02 1.80 1.24 2.81 -0.19 0.17 1.23
= =
=
8
1840
1841 1842 1843 1844 1845 1846 1847 1848 1849 1850 1851 1852 1853 1854 1655 1856 1857 1858 1859 1860 1861 1862 18t3 1864 1865 1866 1867 1868 1869 1870 1871 1872 1873 1874
=
8
A A A A
5
192 351 194 194 4 194 194 194 194 195 195 3 4 352 2 64 26 4 296 352 26 4 352 352 3 52 352 3 52 Z 64 264
-0.13 0.08
-0.29 -0.29 -0.24 0.44 0.55 0.08 0.49
-0.13
0.08 -0.14 -0.14 -0.09 0.09 0.27 0.05
=
=
A A A
0.30 -0.08
-0.11 0.48
-0. 0 6 -0.82 -0.16 0.24 0.38

0.10 1.46 1.44 1.30 1.37 0.87
0.30
0.43 0.30 0.28 0.12 0.15 -0.36 -0.19 -0.45 -0.54 -0.07 0.23 -0.04 -0.11 0.02 -2.60 -0.19 1.09
1675
1876 1877 1878 1879 1880 1881 1882 1883 1884 1885 1886 1887
A A A A A 1-01 A 0.78 A 0.70 A 1.13 A 1.39 A 1.16 A 1.09 A 1.21 A
353
2 60 80 354 67 67 260 5b 353 296 227 227 216 264 26 4
-0.19 1.09
= =
-0.10
-1.60 -0.84 0.75 -2.17 -2.59 0.42 0.29 0.24 0.04
-0.96 0.75 -2.17

1.57 0.29 0.24 1.04
= =
A
1888
1889 1890 cB91 1892 1893 1894 1895 1896 1897 1898 1899 1900
= = 0.04 =
. 91 A 0
-2.13
-2.34 -2.15 1.23 1.38
-0.31
-0.16 -3.68
Z
2 4 186 2 55 218 218 190
A A
-3.58
-1.17 1.23 1.38 1.88 1.92 1.88 1.97 1.95
=
A A A
18 .8
1.92 1.76 1.84 1.84
3
49
CbH8N203 C6H8N208 C6HBN6018 C6H801 C6H802 C6H802 C6H806 C6H806 C6H806 C6HB06 C6H806 C6Hd06 C6H807 C6H807 C6H807 C6H807 C6H807 ~ 6 ~ 8 0 7 ~ ~ 8 0 7 C6H807 C6H807 C6H807 C6H807 C6H9N102 C6H9N301 C6H9N302 CbH9N302 C6HlO CbHlON202 C6HlON206S3 C6HlON401Sl C6HlON40151 C6H10 N6 0 1 C6H 100 1 C6H1001 C6H1001 C6H1001 C6HlOOl C6H1002 CbH1002 C6H1002 C6H1003 C6H1003 c 6~ i o 04 C6H1004 CbH 1 0 0 4 C6H1004 C6H1004 C6H1004 C6H1004 C6H1004 C6H1004 CbHlOO4 C6H1004 C6H1004 C6H1004 C6H1004 C6Hll8RlNZOZ C6HllBRlNZ02 C6HllBRlN202 C6HllBRlN202 CbHll8RlN202 CbHllBRlN202 C bH 11 R 1N2 0 2 B C6H11BR l N 2 0 2 C6H 118R 1NZO2 CbHll8RlN202 CbH116RlN202 CbHllCLlN202 C6HllIIN202 C6H 11K 1 0 2 N C6Hl1 101 CbHllN102 CbHllN102 CbHllN103 1 CbH 1 N103 CCHllNlSl CbHllNAlO2 C6HllNA102 CbH128RlN101 CbHl2BRZO4 C6H 1 2 8R204 C6H12NZ01 CbH12N202 CbH12N202 C6H12N4 CbHl2N4 C6H12N4 C6H1201 C6H1201 CbH1202 CbH1202 CbH1202 C6H1202 C6H1202
IMlSAZOLE-4-CAR8OXAMIOE~5-~3~3-OIME-l-TRIAZENDl~45388l
CVCLOH E X ANONE 0 1 ALLYL ETHER 1-HEX EN-5-ONE
3-4ETHYL-l-PENTVN-3-9L/MEPARFVhOL/
I-PROPVLIDEhE-ACETO\E/MESI TVL O X I D E / 21 4-nEX ANE D 1ON E / PR 0 P IO h VL AC E T3h E / 21 5-dEXAhEO I O N E/AC E TON VL AC ETONE / 21 5-HE XANE3 ION E l AC E T 3 N VL AC ETOQE/ E T HVL AC E T 0 AC E T A T E 4-KETOVALERIC ACIOvYETHVL ESTER A D I P I C ACID A D I P I C ACID A D I P I C ACID A D I P I C ACID AOIPIC A C I O A D I P I C ACID AOIPIC ACID A D I P I C ACID A D I P I C ACIS A D I P I C ACID AOIPIC ACID A D I P I C ACID ETHVLENE GLYCOL OIACETATE ETr(VLEhE GLYCOL OIACETATE A- BROMO-A-M ETHYL BUTVRVLUREA A-BROMO-A-METHYL BUTVRVLUREA A- BROMO- I-VAL ERVLUREA A-BROMO-I-VALERVLUREA/8ROM I SOVALUIII A- BROM O V AL E R VL UR E A A- BROMOVAL ERVLUREA 8- BROMOVAL ERVL UREA G- BROMOVALERVLUREA A-ETHYL-8-8ROMOPROPIOlvVLUREA A-METdYL-8-8ROMOEUT?VLUREA A-HETnVL-G-BROHOBUTVRVLUREA A-CHLORO-I-VAL ERYL UREA A- 1000- I-VAL ERVL UR EA POTASSIUM HEXANOATE 2-AZACVCLOHEPTANONE 0-11-ETHYL-ALLYLICARBAMATE NITROCVCLOHEXANE A- AM I NO 8UTVR 1C AC 10 N- ACE T VL ( 0 1 1 A-AMINOBUTVRIC ACIO~N-ACETVL(OL1 2-ALACVCLDHEPTANTHIONE HEXANOIC A C I O t S O O I J M SALT SODIUM HEXANOATE 2-8ROMO-2-ETHVL8UTVRAHIDE l r 6-01 BROMO-lr 6-01 OEOXVGALAC TITOL ( 1 0 4 8 0 0 1 1t 6-01 BROMO-1 t 6-0 1OEO X VM ANN 1TOL 1 9 4 100) 1~l2~HVOROXYE7HVLJ-2~METHVLIHIOAZOLIhE VALERVLUREA I-VALERVLUREA HE XAHETHVL EN T E T R AM I N E HEXAHETHVL ENET ETRAH INE HEXAMETHYLENETETRAMINE CVCLOHEXANOL 2-HEX ANONE hEXANOIC ACID HEXANOIC A G i Q HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID

NO.

EMPIRICPL FORMULA
A A A A A
SOLVENT CHCL3 CHCL3 OILS BENZENE BENZENE N-BUTANOL I-BUTANOL I-BUTANOL S t C-BUT ANOL XYLENE TDLLENE TOLUENE PRIM. PENTANOLS 2-BUTANONE OCTANE OLEYL ALCOHOL 5-PENTANOLS OODECANE H EX A O E C AN E 1000METHANE OECALIN CHCL 3 OILS BENZENE XYLENE 01 ETHYL Ti-ER OILS OILS OILS I-BUTANOL I-BUTANOL I-BLTANOL I-BUTANOL OCTANOL XYLENE CCL4 N-BUTANOL OCTANOL DIETHYL ETHER N-BETANOL I-BUTANOL OCTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL OCTANOL PRIM. PENTANOLS OCTANOL N-BUTANOL PRIM. PENTANOLS HEX ANOL OCTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL OCTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL N-BUTANOL N-BUTANOL OILS CCL4 CCL4 OILS CCL4 SE C-BUTANOL SEC-BUTANOL OCTANOL OCTANOL OILS OCTANE 000 CAN E HE X I OEC ANE OCTANOL OILS OILS 01 ETHYL ETI'ER OILS OILS 0 1 ETHYL ETkER DIETHYL ETHER OILS DIETHYL ETI-ER OILS DIETHYL ETHER DIETHYL ETkER I-BUTANOL I-BUTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL XVL NE OCTANOL OCTANOL DIETHYL ETHER BENZENE 1-BUTANOL XYLENE TOLUENE
REF FOOT NOTE 29 46 209 44 29 190 4 184 190 46 29 7 190 190 60 5 190
LOGP SOLV 1.05 0.85
LOGP OCT 2.19 1.99 2.01 2.06 2.02 2.12 2.12 2.15 1.46 2.06 2.07 2.48 2.24 2.13 2.20 1.93
NAME HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC A C I O HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID HEXANOIC ACID I-HEXANOIC ACID , I-HEXANOIC ACID I-HEXANOIC ACID I-HEXANOIC ACID PARALDEHYDE PARALDEHYDE PARALDEHYDE PARALDEHYDE RHAHNOS E FRUCTOSE GLUCOSE GLUCONIC ACID 1 12-HYDROXYETHYL )-2-HETHYLIMIOAZOLI NE HCL N- METHY L P I PER IO I NE 01 ETHYLACETAMIOE A-AMINOCAPROIC ACID LEUCINE LEUCINE LEUCINE LEUCINE FRUCTOS E-6-PHO SPHATE FRUCTOSE-6-PHOSPHATE FRUCTOSE-6-PHO SPHATE FRUCTOSE-6-PHOSPHATE GLUCOSE-1-PHOSPHATE GLUCOSE-1-PHOSPHATE GLUCOSE-6-PHOSPHATE GLUCOSE-6-PHOSPHATE GLUCOSE-6-PHOSPHATE GLUCOSE-6-PHOSPHATE SORBOSE-1-PHOSPHATE SORB05 E- 1-PHOSPHAT E SORBOS E-1-PHOSPHATE SDRBOS E- 1-PHOSPHATE SORBOSE-6-PHOSPHATE SORBOSE-6-PHOSPHATE SORBOSE-6-PHOSPHATE SORBOSE-6-PHOSPHATE LEUCINE HYOROCHLORIOE I-LEUCINE HYOROCHLORIOE 01-I-PROPYLFLUOROPHOSPHATE 01-I-PROPYLFLUOROPHOSPHATE 01-I-PROPYLFLUOROPHOSPHATE DI-N-PROPYLFLUOROPHOSPHATE 0 1 -N-PROPYLFLUOROPHOSPHATE LYSINE ARGININE BUTYL- ETHYL ETHER HEXANOL HEXANOL HEXANOL HEXANOL HEXANOL PROPYL ETHER 0 1 ETHYLACETAL 0I ETHYL A C TAL 1.6-HEXANEOIOL 1.6-HEXANEOIOL METHYLPENTANEOIOL 21 4-PENTANEOIOLe Z-METHYL DIETHYLENE GLYCOL MONOETHYL ETHER DIETHYLENE GLYCOL.MONOETHYL ETHER 01 PROPYLENE GLYCOL OIPROPYLENE GLYCOL HEXANETRIOL TRIETHYLENE GLYCOL TRIETHYLENE GLYCOL MANNITOL HExo E ~ I PHOS P HAT E D HEXOSE-OIPHOSPHATE HEXOSE-OIPHOSPHATE
1901 1902 1903 1904 1905 1906 19C7 1908 19C9 1 9 10 1911 19 12 1913 19 14 1915 1916 1917 1918 19 19 1920 1921 1922 1923 1924 1925 1926 1927 1928 1929 1930 1931 1932 1933 1934 1935 1936 1937 1938 1939 1940 1941 1942 1943 1944 1945 1946 1947 1948 1949 1950 1951 1952 1953 1954 1955 1956 1957 1958 1959 1960 1961 1962 1963 1964 1965 1966 1967 1968 1969 1970 1971 1972 1973 1974 1975 1976 1977 1978 1979 1980 1981 1982 1983 1984 1985 1986 1987 19 88 19 89 1990 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000
0.83
0.67 0.63 1.86 1.87 1.89 1.39 0.34 0.56 1.03 2.04 1.36 -0.52 1.65 1.94 -0.72 -0.85 0.81 -0.23 0.90 0.90 0.57
26 47 47 47 26 26
A A A
60
60 7 7 29 220 29 46 2 2 173 296 4 4 4 4 2 16 46 2 34 225 56
0.18
0.95 0.28 0.28 0.45 -1.24 -1.77 -1.96 -1.47 -1.93
2.03 2.02 1.96 1.89 0.95 0.70 0.59
0.70
-2.24 -3.00 -3.29 -2.57 -1.93 0.94 -1.22 -1.71 -3.46 -1.55 -2.21 -0.15
A A A A A 8 8 8
11 46
12
=
8
0.33
-0.45 -0.51 -1.71 -4.92 -0.74 -1.21 -0.15 -1.52
=
B
3
225 4 181 181 181 181 181 181 181 181
181 181 181

181 181 181 181 181 181 181 2 95 295 271 228 271 271 271 84 84 186 56 201 59 59 59 218 173 224 3 2 2
10 10 10 18 10 10 10 10 10 18 10 10 10 18 10 10 10 18 52 52
-0.70
-0.82 -1.00 -1.00 -0.10 -1.05 -1.00 -0.40 -0.10 -0.30 -1.40 -1.00 0.38 -1.00
-1.00
-0.10
*
=
-0.10
0.38
-0.05
0.26 -0.13 -0.08 0.93 1.57 1.58 1.18 1.78 -1.66 -1.49 2.03 2.03 0.88 0.28 0.22 0.11 2.03 0.18 0.90 -0.92 -2.17 -1.62 -0.29 -1.19 -2.22 -1.45 -2.70 -2.51 -2.51 -0.58 -1.85 0.00 -0.69 -0.62 1.20 1.47 1.38 1.33 3.20 -2.82 -2.59 2.03
a
8
8
N
19 19
=
=
A
2.03
1.99
3
2 2 2 2 2
3 4
4 181 181 181 46 218 218
2.03 0.51 1.17 -0.69 -0.74 -0.24 -0.14 -0.93 -0.79 -1.17 -1.23 -2.09 -2.08 -1.32 -3.10
=
8 B A A
A A A A A A A A
10
10 18
02 .3
-0.15 1.17 1.70 1.73 0.95 1.05 1.62 1.24 1.16 1.84 1.70 1.73 1.69 1.28 1.77 1.87 1.47
= =
B
3
205 4 46 68
B B
C6Hl202 C6H1202 C6H1202 C6H1202 C6H1202 C6H1202 C6Hl202 C6H1202 C6H1202 C6H1202 C6H 1 2 02 C6H1202 C6H 12 0 2 C6H1202 C6H1202 C6Hl202 C6H1202 C6H1202 C6H 1 2 0 2 C6H1202 C6H1202 C6Hl202 C6H1202 C6H1202 C6H1202 C6H1203 C6H 1 2 0 3 C6H12 03 C6H1203 C6H1205 C6H1206 C6H1206 C6H1207 C6H13CLIN201 C6H13N1 C6H13N101 C6H13N102 C6H13N102 C6H13N102 C6H13N102 CbH13N102 C6H 1 3 0 9 P 1 C6H1309 P 1 C6H1309Pl C6H1309Pl C6H1309 P 1 C6H1309 P1 C6H1309P1 C6H1309 P1 C6H 1 3 0 9 P 1 C6H1309P1 C6H1309P1 C6H1309Pl C6H1309P1 C6H 1 3 09 P1 C6H 1 3 0 9 P 1 C6H1309Pl C6H 1 3 0 9 P 1 C6H1309 P 1 C6H14CLIN102 CbH16CLlN102 C6H14F103P1 C6H14F103P1 CCH14F 1 0 3 P 1 C6H14F103P1 C6H14F103Pl C6H14N202 C6H14N402 C6H1401 C6H1401 C6H1401 C6H1401 C6H1401 C6H1401 C6H1401 C6H1402 C6H1402 C6H1402 CbH1402 C6H1402 C6H1402 C6H1401. C6H1403 C6H1403 C6H1403 C6H1403 &ti1404 C6H1404 C6Hl406 C6H14012P2 C6H14012P2 C6H14012PZ C6H15N1 C6H15N1 C6H15N1 C6H15N1 C6H15N1 C6H15N1 C6H15N1 C6H15N1
01-I-PROPYL AMINE DIMETHYLBUTYLAMINE 0 1 PROPYLAMINE D I PROPYL AM I NE 0 1 PROPYLAMINE 01 PROPYLAMINE 01 PROPYLAMINE D l PROPYLAM I NE
NO. 2001 2002 2003 2004
SOLVENT
REF FOOT NOTE
LOGP SOLV 2.02 0.89 1.44 1.13 1.32
LOGP OC T 2.34
EMPIRICAL FORMUL A C6H15N1 C6H15N1 CbH15N1 C6H15N1 C6H15N1 C6H15N1 C6HlSN1 C6H15N 1 CbH15N1 C6H15N1 CbH15N101 C6H15N101 C6H15N102 CbH15N102 CbH15N102 CbH15Nl03 C6H15N103 C6H1502PlS2 CbH1504P 1 C6H16N2 C6H16SIl C6H16SI1 CbH18N301Pl CbH18N4 C 7 H l C L 5 N2 C7H2CL2F3N3 C7H38R2N101 C7H3CLlF3N3 C7H3CL2N101 C7H312N101 C7H3N308 C7H48RlNl C7H4F3N3 C7H4F3N3 C7H4N202 C7H4N202 C7H4N206 C7H4N206 C7H4N206 C7H4N206 C7H4N206 C7ti4N206 C7H4N206 C7H4N206 C7H4N404 C7H58R102
NAUE HEXYLAHINE HE XYLAMINE TRIETHYLAMINE TRIETHYLAMINE TRIETHYLAMINE TRIETHYLAMINE TRIETHYLAMINE TRIETHYLAMINE TRIETHYLAMINE TRIETHYLAMINE OIETHYLETHANOLAMINE 01 ETHYLETHANOLAHINE 01-I-PROPANOLAMINE 01-I-PROPANOLAMINE 01-I-PROPANOLAHILE TR IETHANOLAH INE TRIETrlANOLAMINE PHOSPriORODITHIOTIC A C I O ~ O I - I - P R O P Y L PPIOSPHATEI DI-N-PROPYL ETHYLENEDIAHINEI N,NIN'.N'-TETRAHETHYL SI LANE 9 BUTYL-D IH ETHYL SILANE, PROPYL-TRIHETHYL HEXAHETHYL PHOSPHORIC TRIAHIOE TRIETHYLENETETRAHINE BENZIMIDAZOLE~2~4r 5969 7-PENTACHLORO. 4-PYRIOINE IHI OAZOLEI 2-TRIFLOROHE-617-01 CL 4- HY O R O X Y - 3 9 5- 01 BROHO B EkZON 1 TR 1LE 4-PYRIDINE I M I D A Z O L E I ~ - T R I F L U O R O H E - ~ - C L I T R I LE 4-HYOROXY-3.5-DICHLOROBENZON 4-HYOROXY-3s 5-01 IOOO8ENZOkITRILE 2 r 4 r 6 - T R I N I T R O 8 E k Z O I C ACID BRCMOBENLONITRILE 4-PYRIDINE I M I O A Z O L E I ~ - T R I F L U O R O H E T H Y L 5-PYRI 0 I N IM I OAZOLE v 2-TRI FLUOROHE TH VL BENZENEt 3-CYANO-1-NITRO BELZENE~4-tYANO-1-NITRO 21 4-01 NITRO8ENZOIC ACID 21 4-01 N I TROBENZO I C AC I O 2 r 4-DIN ITROBENLO I C AC I O 31 5-DINITROBENZO I C AC I O 3 r 5 - 0 I L I T R O 8 E N Z O I C ACID 3.5-OINITROBENZOIC ACID 3,s-OINITROBENZOIC A C I O 31 5-01 NITROaEL 20 I C AC I O 5,7-OINITRO8ENZPYRAZOLE IPUA = 1.20/ H-8ROHOBENLOIC ACID M-8ROHOBENZO I C A C I O 0- BROMOBENZOI C A C 10 P-BROMOBENZOIC A C I 0 8ENZOXAZOLE~2-AMINO-5-CHLORO/ZOXAZOLAMINE/ H-CHLOROBENZOIC ACI 0 H-CHLOROBEN 201 C AC IO M-CHLORO8EN ZO I C AC I O 0-CHLOROBENZOIC AC IO 0-CHLOROBENZO I C AC IO 0- CHLO RO BEN 20 1C AC I 0 0-CHLORO8ENZOIC A C I J 0-CrlLOROBEkZOIC ACID 0-CHLORJ8ENZOIC ACID P-CHLOROBEQLOIC AC I O P- CtlLOROBEh 20 I C AC IO P-CHLOROBENZO I C AC 1I I A, A, A-TRICHLOROTOLUENE H-FLUOROBENZOIC ACID P-FLUOROBENZOIC ACID BENZENEI T R I FLUOROMETHYL 3-TRICHLOROHETHVL-4-YITROBENZENESULFONAMIOE 3-TRICHLOROHET~VL-4-NITRO8ENZEhESULFONAMIOE BNZENEe TRIFLUOROMtTHOXV M-Td IFLUOROHEThYLPtlENOL 0-TR1FLUOROHEThYLPnEhOL
SJLFOhEvPrlENYL-TRIFLUOROMETHYL
2005
2006 20C7 2008 2009 20 1 0 2011 2012 20 13 20 1 4 2015 20 16 2017 2018 2019 2020 2021 2022 2023 2024 2025 2026 2027 2028 2029 2030 2031 2032 2033 2 0 34 2035 2036 2037 2038 2039 2040 2041 2042 2043 2044 2045 2046 2047 2048 2049 2050 2051 2052 2053 20 54 2055 2056 20 57 2058 2059 2060 2001 2002 2063 2004 2065 2066 2067 2068 2069 2070 2071 2072 2073 2074 2075 2076 2077 2078 2079 20 EO 2081 2082 2083 20 8 4 2085 2086 2087 2088 2089 2090 2091 2c92 2093 2094 2055 2096 2097 2098 2099 2100
I-BUTANOL 4 XYLENE 46 OCTANOL 2 18 BENZENE 3 55 I-BUTANOL 4 46 XYLENE TOLUENE 68 TOLUENE 66 355 TOLUENE PRIH. PENTANOLS 182 3 DIETHYL EThER I-BUTANOL 4 5 OCTANOL DIETHYL ETHER 3 I-BUTANOL 4 DIETHYL ETHER 3 1-BUTANOL 4 CCL4 135 PRIM. PENTANOLS 236 OC T ANOL 56 OCTANOL 2 98 OCTANOL 298 OCTANOL 56 I-BUTANOL 4 OCTANOL 206 OCTANOL 206 HEXANE 2 99 OCTANOL 206 HEXANE 299 HEXANE 299 OIETHYL ETFER 46 173 OILS 206 OCTANOL OCTANOL 206 OCTANOL 10 OCTANOL 10 0 I ETHYL ETHER 46 46 CHCL 3 46 XYLENE 149 CHCL3 46 CHCL3 356 CHCL3 46 XYLENE HE-I-8UT.K ETONE 149 276 OC T ANOL OCTANOL 10 29 CHCL3 CHCL~ 29 OCTANOL 10 OCTANOL 218 OCTANOL 10 CHCL3 29 TOLUENE 29 OCTANOL 65 DIETHYL ETtER 46 CYCLOHEXANE 357 CHCL3 29 XYLENE 46 TOLUENE 29 OCTANOL 10 CHCL3 29 TOLUENE 29 OCTANOL 235 OCTANOL 10 OCTANOL 10 OCTANOL 56 OCTANOL 217 CHCL3 217 OCTANOL 56 OCTANOL 10 OCTANOL 261 0 CT ANOL 56 0 C T ANOL 56 OCT ANOL 10 OCTANOL 65 DIETHYL ETHER 46 CHCL 3 46 XYLENE 46 10 OCTANOL OCTANOL 10 CYCLOHEXANE 358 OCTANOL 309 OCTANOL 10 OCTANOL 10 DIETHYL E T t E R 112 OCTANOL 65 DIETHYL ETtER 3 59 DIETHYL ETtER 113 113 CHCL3 I-PENT. ACETA T E 359 OCT ANOL 10 0 1 ETHYL ETtER 46 CHCL3 29 CHCL3 2 54 BENZENE 356 XYLENE 46 TOLUENE 29 N-bEPTANE 254 OIETHYL ETHER 46 CYCLOHEXANE 357
1.52 e
11 .1
1.90 0.76 0.92 1.42 -0.46
1.44 1.30 1.47 1.77 1.37 1.20 1.32 1.42 0.46
8 8 8
8 8
0.58
-0.82 -2.23
0.31
-0.82 -1.10 -0.72 -1.75 -1.32 1.67 0.62 3.57 3.84 0.28 -1.66 4.53
=
8
8
-0.15
-2.96 -0.58 1.90 0.73
17
0.30
3.57 3.84 0.28 -0.82 4.53 3.50 0.49 2.69 -0.14
0.30 =
= = = =
=
27 27
3.50
2.69
=
A A
10 .8
27 27
0.27 2.61 1.23 0.94 1.17 1.19 1.18
-0.88
-0.92 0.18 0.07 -0.20 0.09 2.48 1.60 2.87 2.04 0.91 2.86 2.46 2.68 1.92 1.12 1.98 2.14 -0.34 0.90 0.01 0.27 2.65 1.72 1.26 2.92 2.15 2.07 2.79 1.73 0.19 3.17 2.95 2.80 2.71 3.79 3.13 2.40 3.11 1.09 0.49 3.02 1.56
12
0.36 3.56 1.23 0.94 1.17 1.19 1.16 0.42 0.79 1.38 1.28 1.04 1.90 2.22 1.60 2.87 3.07 2.05 2.86 2.46 2.68 3.05 2.56 1.98 2.00
2.03 1.80 1.81 2.65 2.78 2.68 2.92 2.15 2.07 2.79 1.73 1.44 3.17 2.95
= =
=
=
A A A A A A A
= =
= = =
A A
A A
=
A
A A A
=
A A
07 07
= = = = =
A
28 .0
2.71 3.79 3.13 2.40 2.85 2.21 2.32 3.02 1.56 1.59 1.70 1.60 0.91 0.67 0.64 1.17 1.39 1.83 1.85 1.66 1.55 1.58 1.83 1.66 1.52
= =
= A
A A
= = =
= = = =
1-06
1.59 1.70
16 .0
16 16 16 12 1.79 0.91 0.64
= =
A A
A
1.68 A
06 .0 -0.06 1.51 1.83 1.97 0.48 0.41 0.21 0.02 0.09 -1.22 1.59 -0.88
=
A A A A
A
C7H5CL102 C7H5CL 1 0 2 C7H5CL102 C7H5CL 1 0 2 C7H5CL102 C7H5CL102 C7H5CL102 C7H5CL102 C7HSCL102 C7H5CL102 C7H5CL102 C7H5CL3 C7H5F102 C7H5F102 C7H5F3 C7H5F3N204Sl C7H5F3N204S1 c7n5F301 C7H5F301 C7H5F301 C7H5F302S1 C7H5F351 C7HJI 102 C7H51102 C7H51102 C7H5I 1 0 2 C7H51102 C7H51102 C7H5N1 C7H5N1 C7H5N101 C7H5N101 C7H5N101 C7HSN101Sl C 7HSN103S 1 C7H5N103S1 C7H5N103S1 ClH5N103Sl C7H5N103Sl C7H5N104 C7H5N104 C 7H 5 N 10 4 C7H5N104 C 7H5N 1 0 4 C7H5N104 C7H5N104 C7H5N104 C7H5Nl04 C7H5N104
BENLEkEt TRIFLUOROMETHYLTrlIO n - I o o g a E h z o I c ACID
0- IO008 E h Z O I C AC I O 0- 10 00 8 E h Z O I C A C 10
0-IOOOBENZOIC ACID 0- 1009 B E N L O I C AC IO P-IOOOBENZOIC A C I O BtNZON I TRIL E 8EhZON I T R I L E BEhLOXAZOLE M-CYAhOPHENOL P-CY ANOPh ENOL BcNZOXAZOLTnIOh SACCrlARIh SACCHARIh SACCdARIk
SACCHAR I h
SACCdAR I h
H-hlTROBEkZOIC
H-kITRO8ENZOIC M-hITRO5EhZOIC M-hITRO8EkZOIC H-kITROt3E\ZO I C M-hlTRO8ENZOIC H-NITROBEkZOIC H-hITRO8ENZOIC O-NIT?O8EhZOIC 0-NITROBEhZ3IC
ACID ACIO
ACIO
ACIO AC I O ACIJ
ACID ACID ACID AC13

REF FOOT NOTE 29 46 307 356 46 29 10 29 307 46 29 186 309 218 238 206 LDGP SOLV LOGP DCT 1.25 1.04 1.12 1-16 1.31 1.30 1.89 2.00 1.67 1.85 2.03 2.01 3.28 1.64 -0.85 -0.37 2.39 1.82 1.34 1.50 EMPIRICAL FORMULA NAME
NO. 2101 2102 2 103 2104 2105 2106 21C7 2108 2109 2110 2111 2112 2 1 13 2114 2115 2116 2117 2 1 18 2119 2120 2121 2122 2123 2124 2125 2126 2127 2128 2129 2130 2131 2132 2133 2134 2135 2136 2137 2138 2139 2140 2141 2142 2143 2144 2145 2146 2147 2148 2149 2150 2151 2152 2153 2154 2155 2156 2157 2158 2159 2160 2161 2162 2163 2164 2165 2166 2167 2168 2169 2170 ' 2171 2172 2173 2174 2175 2176 2177 2178 2179 2180 2181 2182 2183 2184 2185 2186 2187 2188 2189 2190 2191 2192 2193 2 194 2195 2196 2197 2198 2199 2200
SOLVENT CHCL3 CHCL~ BENZENE BENZENE XYLENE TOLUENE 0 C T ANOL CJiCL3 BENZENE XYLENE TOLUENE OCTANOL OCTPNOL OCTANOL OCTANOL OCTANOL OCTANOL OILS BENZENE BENZENE 0 C T ANOL OCTANOL OCTANOL OCTANOL OCTANOL DIETHYL Eli-ER CHCL3 OCTANOL OCTANOL CHCL~ OCTANOL DIETHYL ETi-ER CYCLOHEXANE CYCLOHEXANE BENZENE CLCHZCHZCL OCTANOL DIETHYL ETI'ER DIETHYL ETkER oIETnyL E T ~ E R CHCL3 CHCL~ CHCL~ CHCL3 OILS OILS BENZENE BENZENE BENZENE BENZENE BENZENE BENZENE I-BUTANOL XYLENE XYLENE TOLUENE TOLUENE CCL4 ETHVL BENZOATE 01-PENTYL ETHER N-HEPTANE PARAFFINS DIETHYL ETHER BENZENE CLCHZCHZCL DCTANOL OCTANDL TOLUENE DIETHYL ETHER CHCL~ BENZENE CCL4 CLCHZCHZCL CLCHZCH2CL DI-I-PR. ETHER OCTANOL CHCL3 OCTANOL DIETHYL ETHER I-BUTANOL OC T AND L OCTANOL DIETHYL ETHER 0 1 ETHVL ETHER CYCLOHEXANE CYCLOHEXANE CHCL3 CHCL3 CHCL3 CHCL3 OILS BENZENE BENZENE I-BUTANOL XYLENE TOLUENE CCL4 ETHVL BENZOATE N-HEPTANE ME-I-8UT.KETONE
0.03 -0.19 -0.30
A
A A A A A
-0.21
-0.35 -0.32 1.89 0.86 0.31 0.07 0.51 2.01 2.03
=
A A
A
A
= 2.03 =
=
3.28
78 6 3.22 1.64 -0.85 -0.97 0.35 -1.71 2.39 1.82 1.34 1.50 1.20 -0.02
3.22 =
=
= 8 = =
216
292 311 311 206 216 218 206 3 60 112 112 309 217 217 235 248 141 248 248 248 10 3 46 36 29 39 2 54 17 361 3 62 29 39 38 3 63
= =
=
B A
1.20
0.82 1-12 1.82 0.23 0.01 1.48 2.41
50 07 07 50 50
-0.10
1.82 0.23 -0.61 1.48 1.74 1.13 1.34
=
N
=
8
2.10
2.35 1.87 1.89 1.78 1.85 0.71 0.30 0.46 0.54 0.66 0.54 0.21 0.24 0.18 '0.21 0.36 0.12 1.69 -0.19 0.44 0.36 0.48 -2.90 1.50 0.95 -0.72 -0.12 1.32
2.00
1.87 1.78 1.68 1.72 1.86 1.51 1-60 1.73 1.86 1.71
=
A A A A A A A A A A P A
1.58
1.61 1.55 1.17 1.73 1.49 1.87 1.58
36
12
Q
A A
20 4 46
A
A A
36
29
12
2.23
1.90
36 36 4 17 17 254 291 248 248 248 365 268 150 3 66 366 366
2.00 A
12
1.27
-0.16
32 0.44 1.70 1.81 2.15 1.10 -0.12 -0.55 -1.70 0.11 0.21 0.84 0.53 1.70 1.50 1.32 1.40 2.26 2.21 2.37 2.53 -1.02 -0.50 0.48 0.50 0.34 0.46 1.00 0.45
1.21
1.70 1.81 2.70
A A
= =
8 1.08 A 1.11 A 0.87 A

A
366 366
248 3 66 9 367
0.41 1.51 0.53 1.21 1.50 1.27 1.47 2.26 2.21 2.20 2.32 1.66 1-67 1.46 1.60 2.10 1.81 1.88 2.31 1.93 1.80
=
8
12
10 3 4 186
218
=
A
=
A A
3
46 15 3 57 149 29 39 254 173 39 368 4 46 29 17
12
68
0.38
2.13 0.11 0.31
A A A A A A
A A
-0.30
1.90 -0.92 2.51 2.25
17 25 4
a49
C7H5N104 C7H5N104 C7H5N104 C7H5N104 C7H5N104 C7H5N104 C7H5N104 C7H5Nl04 C7H5N104 C7H5N104 C7H5N104 C7H5NlS.l C7H5NlS1 C7H5N1 S 1 C7H5NlS1 C7H5N302 C7H5NA103 C7H5NA103 C7H681F302 C7H681N106 C7HbCLlN3Sl C7H6NZ C7H6N2 C7H6NZ C7HbN2 C7HbNZ C7H6N2 C7H6N2 C7H6N202S1 C 766 N2 02s 1 C7H601 C7H601 C7H601 C7H601 C7H601 C7H601 C7Hb02 c7~602 C7H602 C7H602 C7Hb02 C7H602 C7H602 C7Hb02 C7H602 C7H602 C7H602 ~ 7 ~ 6 0 2 C7Hb02 ~ 7 ~ 6 0 2 C7H602 C7H602 ~ 7 ~ 6 0 2 C7Hb02 C7H602 C7Hb02 C7H602 C7H602 C7H602 C7H602 C7H602 C7H6D2 C7H602 C7H602 C7H602 C7H602 C7H602 C7H602 C7H602 C7H6D2 C7H602 C7H602 C7H602 ~ 7 ~ 6 0 2 C7H602 C7H602 C7H602 C7H603 C7H6D3 C7H6D3 C7H603 C7H603 C7H603 C7H603 C7H603 C7H6D3 C7H603 C7H6D3 C7H603 C7H6D3 C7H6D3 C7H6D3 C7H6D3 C7H603 C7H603 C7H6D3 C7H603 C7H603 C7H603 C7H603
0-NITROBENZOIC ACID 0-NITROBENZOIC ACID 0-N I T R O B EN ZO I C AC I 0 0-NITRO8ENZO I C A C I 0 0-NITROBENZO I C A C I 0 0-NITROBENZOIC ACID P-NlTROdENZJIC ACID P-NITROBE\ZOIC A C I D P-NlTROSEhZO I C A C IO P-NITROBENZO I C A C I 0 P-hITROBENZOIC ACID BENZOTHIAZOLE 8ENZOTnIAZOL E PHEYYLIS3TtiIOCVAhATE PHENYL I SOTH I O C Y AN A T E 8ENZ IHIDAZOLEI 5-NITRO SOD1UH SAL I CYL A T E SODIUM SALICYLATE PHENYL BORON I C AC I O v 3-TR I FLUOROME THYL PHENYLBORONIC AC I O t 3 - N ITROI~-CARBOXYL 4-PYRIDINE I M I O A Z O L E I Z - W E T H Y L T H I O - 6 - C H L O R O 7- A2 A I NOOL E BENZ I M IOAZOLE BENZ I H I DAZOLE BENZIMIOAZOLE BENZIMIDAZOLE B E N Z I H I DAZOL E INOAZOLE
P-CYANOBENZENESULFONAMIOE
P-CY ANOBENZENESULFONAM BENZAL DEHVOE BENZAL OEHVDE BENZALOEHYOE BENZALDEHYDE BENZALDEHYDE BENZALOEHYOE BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID D E I
BENLOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID BENZOIC ACID M-HYOROXVBENZALOEHYDE H-HYDROXVBENZALDEHVDE M- HY DROXV BENZAL 0 EHY DE 0-HVDROXYBENZALOEHYOE/SAL CYLALOEHYOE/ 0-HVDROXVBENZALOEHYOE/SAL CVLALDEHVDE/ 0-HYOROXYBENZALDEHYDE/SAL CYLALOEHYOE/ P-HYDROXYBENZALOEHYOE P-HYDROXVBENZALDEHVOE P-HYOROXYBENZALOEHVDE P-HYDROXY BENZALDEHYDE P-HY ORDXY BENZALDEHYDE P-HYOROXVBENZALOEHVOE P-HVORDXY BENZALDEHYDE TROPOLONE TROPOLONE . -. .M-HVDROXVBENZO I C ACID H-HVOROXYBENZOIC ACID ~ . . M-HYOROXYBENZOIC ACIO 0-HYDROXY 8ENZO I C A C I O I SALICYLIC AC I O / 0-HYDROXYBENZOIC A C I D / S A L I C V L I C ACID/ D-HYDROXYBENZOIC ACIO/SALICYLIC ACID/ 0-HYDROXYBENZOIC ACIO/SALICYLIC ACID/ 0-HYDRDXYBENZOIC ACIO/SALICVLIC ACID/ 0-HYORDXV8ENZOIC A C I D I S A L I C Y L I C ACID/ 0-HYOROXYBENZOIC AC 1O / SA L I CVL I A I O / C C 0-HY ORDXY BENZOIC ACIO/SALICYLIC ACID/ 0-HVOROXYBENZDIC A C I O I S A L I C Y L I C ACID/ 0-HYOROXVBENZO I C ACIO/SALICYLIC ACID/ 0-HVORDXYBENZO I C ACIO/SALICYLIC ACID/ 0-HYOROXYBENZOIC AC I D / SAL I C V L I C A I O / C 0-HYDROXYBENZOIC A C I D I S A L I C Y L I C ACID/ 0-HYOROXVBENZOIC A C I O I S A L I C Y L I C ACID/ D-HVDROXVBENZO I C ACIO/SALICVLIC ACID/ D-HYOROXVBENZDIC ACIO/SALICYLIC ACID/ D-HYDROXY BENZD I C 0-HVOROXYBENZDIC 0-HVOROXYBENZO I C A C I O I S A L I C Y L I C ACID/ 0-HVOROXYBENZDIC ACID/SALICVLIC ACID/

LOGP OCT 1.58 1.36 1-00 -0.59 1.45 1.51 -0.02 1.44 1.31 -0.21 -0.20 2.20 1.39 -0.15 -0.25 -1.25 -1.17 -1.54 EMPIRICAL FORWLA NAME P-HYOROXYBENZOIC ACID P-HYDROXYBENZOIC ACID P-HYOROXYBENZOIC ACID P-HYOROXYBENZOIC ACID P-HY DROXYBENZO I C ACID P-HYOROXYBENZOIC AC I O P-HYDROXY BEN ZO I C ACID P-HYOROXY8ENZOIC AC I O 2.4-OIHYOROXYBENZOIC ACIO/RESORCYLIC ACID/ 2.4-01 HYOROXYBENZOI C AC IO /RESORCYLIC AC I O / 2.5-01 HYDROXY BENZOIC AC IO/GENTI SIC ACID/ 2 1 5-DIHYOROXYBENZOIC ACIO/GENTI SIC A C I O l Z15-OIHYOROXYBENZOIC ACIDIGENTISIC A C I O l 2.6-OIHYOROXYBENZOIC ACID 3r5-D1HYOROXY8ENZOIC ACID 3.4.5-TR I HY OROXY BEN 20 I C AC I O/GA L L I C AC IO/ 3.4r5-TR1HYDROXYBENZOIC ACIO/GALLIC ACID/ SULFOSALICYLIC ACIO/3-CO2H-4-OH-BENZENESULFONIC SULFOSALICYLIC ACIO/3-CO2H-4-OH-BENZENESULFONIC SULFOSALICYLIC ACIO/3-COZH-4-OH-BENZENESULFONIC P-FORMYLPHENYLBORONIC A IO C M-CARBOXYPHENYLBORONIC ACID P-CARBOXYPHENYLBORONIC ACID A- BROMOTOLUEN E A-CHLOROTOL UENE M- CHLOROTOLUENE 0-CHLOROTOLUENE P- CHLO ROTOLUENE PURINEI~I~-OI-IMETHYLSULFONYLI-~-~HLORO PURINE~2~8-DIMETHYLTHIOI6-CHLORO M-CHLOROBENZYL ALCOHOL P- CH LO R 0 8ENZ YL ALCOHOL PHENOLI 4-CHLOROv 3-METHYL PHENOLv4-CHLOROv3-METHYL PHENOL*~-CHLOROI 3-METHYL PHENOL, 4-CHLOROt 3-METHYL P-FLUOROSULFONYLTOLUENE POTASSIUM GUAICOLATE BENZAL OOXIME BENLAMIOE BENLAM I O BENZAM I O E BENZAMIOE BENZAMIOE BENZAMIDE BENZAM I O BENZAMIOE BENZAMIOE BENZAMIOE BENZAMIOE BENZAM IDE FORMANIL I O E M- AM INOBENZO I C ACI D M-AMINOBENZOIC A C I O 0-AMINOBENZOIC ACID/ANTHRANILIC ACID/ 0-AMINOBENZOIC ACIO/ANTHRANILIC ACID/ 0-AMINOBENZOIC ACIOIPNTHRANILIC ACID/ 0 - A M INOBENZOIC A C I DlANTHRANI L I C AC IO/ 0-AMINOBENZOIC ACIO/ANTHRANILIC ACID/ 0-AHINOBENZOIC ACID/ANTHRANILIC ACID/ 0-AHINOBENZOIC ACIO/ANTHRANILIC ACID/ 0-AMINOBENZOIC ACIO/ANTHRANILIC ACID/ P-AMINOBENZOIC ACID P- AM INOBENZOIC ACID P-AMINOBENZOIC ACID 0-HYDROXYBENZAMIOE/SALICYLAMIOE/ 0-HYOROXYBENZAMIDE/SALICYLAMIDE/ 0-HYOROXYBENZAH I OEISAL ICYLAM IOE / 0-HYOROXYBENZAMIOE/SAL ICYLAM I O E / 0-HYDROXYBENZAMIOE/SAL ICYLAMIOE/ 0-HYOROXYBENZAM I OE/SAL ICYLAMIOE / 0-HYDROXY BENZAMI DE /SAL ICYLAMIOE / I - N I C O T I N I C ACIOvMETHYL ESTER M- N I TROTOL UEN E M- NITROTOLUENE 0 - N I TROTOLUENE P-N I TROTOL UEN E P-NITROTOLUENE 0-PHENYL CARBAMATE P-AMlNOSAClCYLIC ACID M-N1 T R 0 AN I SOL E P-NITROANI SOLE M-N I T R O BENZYL ALCOHOL P-NITROBENZYL ALCOHOL SODIUM GUAICOLATE TOLUENE TOLUENE TDLU EN E TOLUENE TOLUENE HYOROCHLOROTHIAZIOE P-NITROSOMETHYLANILINE PHENYLUREA PH ENYLUREA PHENYLUREA PHENYLUREA PH ENYL UREA PHENYL THIOUREA PHENYL THIOUREA PHENYL T H IOURE 4,
NO. 2201 2202 2203 2204 2205 2206 2207 2208 22C9 22 10 2211 2 2 12 2213 22 1 4 22 15 22 16 2217 2218 22 19 2 2 20 2221 2222 2223 2224 2225 2226 2227 2228 2229 2230 2231 2232 2233 2234 2235 2236 2237 2238 2239 2240 2241 2242 2243 2244 2245 2246 2247 2248 2249 2250 2251 2252 2253 2254 2255 2256 2257 2258 2259 2260 2261 2262 2263 2264 2265 2266 2267 2268 2269 2270 2271 2272 2273 2274 2275 2276 2277 2278 2279 2280 2281 2282 2283 2284 2285 2286 2287 2288 2289 2290 2291 2292 2293 2294 2295 2296 2297 2290 2299 2300
SOLVENT
REF FOOT NOTE
LOGP SOLV 1.58 1.42 1.00 -2.00 0.22 1.43 0.75 -0.39 -1.66 1.55 1.35 -1.57 -1.82 2.20 1.45
OCTANOL DIETHYL ETHER DIETHYL ETI-ER CHCL3 OILS I-BUTANOL ETHYL BENZOATE 01-PENTYL ETHER XYLENE ME-1-BUT.KETONE 0 I ETHYL ETHER CHCL3 XYLENE OCTANOL DIETHYL ETCER o I E T n Y L ETHER 01 ETHYL ETHER DIETHYL ETt-ER ME- I-BUT . ETONE K S-PENTANOLS BENZENE BENZENE BENZENE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE METH. OECANOATE OLEYL ALCOHOL OCTANOL I-OCTANOL OCTANOL OCTANOL DIETHYL TI-ER CHCL3 OILS OILS OILS OILS OILS BENZENE CCL4 CLCHZCH~CL OLEYL ALCOI-OL OCTANOL DIETHYL T I - E R I-BUTANOL OCTANOL DIETHYL TI-ER DIETHYL ETHER 01 ETHYL E T F E R CHCL3 CHCL3 BENZENE I-BUTANOL OCTANOL oIETnYL E W E R I-BUTANOL OCTANOL OILS OILS
10
=
A
A A A
3
46 254 3 69 4 17 17 46 195 46 46 46 56 46 12
12 12 12
A A A
=
A A A A
3
46 207 195 195 311 311 311 218 302 301 301 301 206 206 10 10 261 124 124 124 65 353 235 10 248 248 173 82 293 249 70 248 248 248 82
56
-0.30
-0.42 -1.56 -1.25 -1.08 -1.46 -2.52 -1.83 2.92 2.30 3.28 3.42 3.33 3.70 0.63 1.94 1.96 3.10 0.15 2.65 2.46 2.74 -2.83 1.75 0.64 -0.22 0.11 -0.51 -0.36
6 6 6
26
27
2.92 2.30 3.28 3.42 3.33 3.70 0.63 1.94 1.96 3.10 3.14 3.00 2.74
=
= =
= =
= = =
-0.66
-0.42 -0.36 -0.71 -1.54 0.00 0.40 1.15
1.75 = 0.64 = 0.65 8 0.71 N 0.73 A 0.87 A 0.59 A 0.81 A 0.89 A 0.68 A
OILS
OILS OILS OLEYL ALCOPOL CHCL3 OC TANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL N-HEP TAN E OCTANOL OCTANOL OCT ANOL OCTANOL I-OCTANOL O C T ANOL OCTANOL OCTANOL OCTANOL N-HEPTANE OCTANOL BENZENE OCTANOL OCTANOL 01 ETHYL E T r m DIETHYL ETt-ER CHCL3 OCTANOL DIETHYL ETI-ER CHCL3
3 4 56 3 112 46 112 29 72 4 65 3 4 186 173 224 82 293 70 82 318 10
0.18
0.46 1.21 1.43 1.48 0.05 0.57 -1.15 -0.27 1.18
0.68
c. 9 6 1.15 = 0.27 A
0.14
1.21 1.37 1.41 0.17 1.73 0.27 1.11 1.15
=
A A A A A A
2 2 5
0.68
0.89 0.75 1.28 1.60 1.56 1.50 2.23 1.33 1.49 2.45 2.40 2.30 2.37 2.42 1.08 2.16 2.03 1.21 1.26 2.69 2.73 2.11 2.80 -0.07 0.91 0.83 0.82 0.81
=
A
0.88
0.89 1.28 0.45 1.15 0.41 0.34 1.15 0.77 2.01 2.45 2.40 2.30 2.37 2.42 1.08 -1.04 2.16 2.03 1.21 1.26 -2.62 2.69 2.73 2.11 2.80 2.85 -0.07 0.51 0.83 0.82 0.04 -0.26 -0.72 0.73 0.23 0.54
=
A
A A
A
2 2
301
301 10 301 56 370 10
10
= = = =
= = = =
14
10 10 353 10 56 309 301 310 2 18 72 5b 235 3 113 113 235 248 248
=
= = =
=
B
= = 8
A N
-0.10
-0.07 0.73 0.32 1.10
12
=
A N
C7H603 C7Hb03 C7H603 C7H603 C7H603 C7H603 C7H603 C7H603 C7H604 C7H604 C7Hb04 C7H604 C7H604 C7H604 C7H604 cmt.05 C7H605 C7H606S1 C7H606S 1 C7H60651 C7H78103 C7H78104 C7H78104 C7H7BR1 C7H7CL 1 C7H7CL1 C ~ H ~ C L ~ C7H7CLl C7H7CLlN404SZ C7H7CLlN4SZ C7H7CL101 C7H7CL101 C?H7CL101 C7H7CL101 C7H 7CL 1 0 1 C7H7CL101 C7~7FlO2S1 C7H7K102 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N101 C7H7N102 C7H7N102 C7H7NlO2 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N102 C7H7N103 C7H7N103 C7H7N103 C7H7N103 C7H7N103 C7H7NA102 C7H8 C7H8 C7H8 C7H8 C7H8 C7H8CL1 N304S 2 C7HBN201 C7H6N201 C7HBN201 C7HBN201 C7H8N201 C7HBN201 C7H8N2S1 C7H8N2Sl C7H8N251
ACID/ ACID/ ACID/

NO. 2301 2302 2303 2304 2305 2306 2307 2308 2309 2 3 10 2311 2312 23 13 23 14 23 15 23 16 2317 23 18 23 19 23 20 2321 2322 2323 23 24 23 25 2326 2327 2328 2329 2330 2331 2332 2333 2334 2335 2336 2337 2338 2339 2340 234 1 2342 2343 2344 2345 2346 2347 2348 2349 2350 2351 2352 2353 2354 2355 2356 2357 2358 2359 2360 2361 2362 2303 2364 2365 2366 2367 2368 2369 2370 2371 2372 2373 2374 2375 2376 2377 2378 2379 2380 2381 2382 2383 2384 2385 2386 2387 2388 2389 2390 2391 2392 2393 2394 2395 2396 2397 2398 2399 2400 SOLVENl OCTANOL OCTANOL OCTANOL CHCL3 CHCL3 OILS OCTANOL CHCL3 CHCL3 OILS CCL4 N-PEPTANE OCTANOL OCTANOL DIETHYL ETkER CYCLOHEXANE OCTANOL CYCLOHEXANE HEXANE OCTANOL OCTANOL DIETHYL E l l - E R CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OILS OILS BENZENE N-BUTYL ACETATE METH. DECANOATE N-HEPTANE OLEYL ALCOHOL PARAFFINS OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OILS N-BUTYL ACETATE METh. OECANOATE N-HEPTANE OLEYL ALCOHOL PARAFFINS OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OILS N-BUTYL ACETATE N-HEPTANE OLEYL ALCOHOL PARAFFINS DIETHYL ETCER 01-BUTYL ETHER 01-I-PR. ETHER OCTANOL OCTANOL OCTANOL OCTANOL OLEYL ALCOHOL 0 1 ETHYL ETHER OILS OILS OLEYL ALCOHOL PARAFFINS OCTANOL DIETHYL ETHER CYCLOHEXANE OLEYL ALCOHOL OCTANOL OCTANOL OCTANOL OCTANOL 0 1 ETHYL ETHER CHCL3 OCTPNOL BENZENE BENZENE BENZENE BENZENE BENZENE OCTANOL OCTANOL OCTANOL CYCLOHEXANE OCTANOL DIETHYL ETCER DIETHYL ETCER DIETHYL ETHER CHCL3 BENZENE I -BUTANOL XYLENE N-CEPTANE CHCL3 OCTANOL OCTANOL CYCLOHEXANE REF FOOT NOTE 226 65 218 2 54 322 371 218 254 322 371 2 34 2 54 10 309 323 358 10 141 372 10 301 329 124 132 325 133 324 327 324 331 124 LOGP SOLV 1.04 1.04 -0.78 -0.40 -0.91 0.19 -0.02 -0.52 -0.86 0.21 -2.70 -1.70 2.11 2.04 2.46 2.30 1.10 -0.62 -0.76 1.96 2.01 1.80 -0.30 -0.15 -0.20 -0.10 1.29 1.21 LOGP OCT 1.04 1.04 -0.78 -0.45 -0.85 1.36 -0.02 -0.54 EMPIRICAL FORMULA C7HBN401S1 C7H8N40151 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H8N402 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7HSO1 C7H8Ol C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 C7H801 NAME
8 8
A
12 12 12 12
B
8
B
-0.80
0.46 2.11 2.04 2.27 1.10 1.96 2.01 1.70
=
A
50
= = =
A
45
08 .8
2.19 1.83 -0.35 1.79 -0.51 1.95 0.04
2.37 2.28 2.24 1.98 2.29 2.34 1.95
A A A
3 10
124 327 216 124 132 325 133 327 331 124 3 10 124 327 10 301 132 325 327 331 310 124 327 332 332 332 10 10 276 10 124 323 224 327 124 327 10 323 56 124 186 56 349 349 113 113 56 311 311 311 311 311 373 312 218 337 255
0.13
0.10 0.20 1.34 2.20 1.93 -0.05 1.81 -0.14 1.94 1.92 -0.10 -0.19 1.21 2.28 -0.35 1.80 -0.58 1.23 0.50 0.94 0.49 0.25 0.73 1.58 1.15 1.36 1.48 0.96 1.15 2.49 1.98 2.40 2.36 1.94 1.92
= =
1.20 1.64 0.49 0.25 0.73 1.58 1.70 1.31 2.53 2.06 1.70 1.34 1.31 1.56 0.47 0.50 2.33 1.52 1.62 3.39 2.74
A
A A
=
=
12
0.30
1.34 1.36 -1.08 1.00 0.47 0.50
= A
2.33
50
6
6
6 6 6
3
46 37 4 4b 315 4 46 315 280 10
1.52 1.72 2.98 2.74 -0.20 -0.16 -0.19 0.17 -0.43 -2.02 1.82 1.66 1.23 1.09 0.28 0.32
A N
-2.02 1.82 1.66 1.09 1.11 1.14 1.14 0.78 0.97 0.87 0.86 1.40 1.43
* =
=
B B B B B
03 .6
1.18 0.61 0.98 0.30 -0.21 2.30 1.40 1.43 0.64
301
337
--
C7H801 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802 C7H802S1 C7H802S1 C7H802Sl C7H803 C7H803S1 C7H803S1 C7H8Sl C7H9B102 C7H9B102 C7H96102 C7H9B102S1 C7H98103 C7H9CLlNZ01 C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N1 CTH9Nl C7H9N1 C7H9N1 C7H9N1 CTH9N1 C7H9N1
5 - H Y O R O X Y P I C O L I N A L O E H Y O E THIOSEMICARBAZONE(1073921 5-HYOROXYPICOL INAL DE HYOE THIOSEMICARBAZONE ( 10 7 3 9 2 ) THEOBROMINE/3r 7-DIMETHYL XANTHINE/ TH EOBROMINE/ 3.7-01 METHYL XANTHINE / T H E BR OH I N E I 3 I 7- 0 I ETH YL XA NTH I / O M NE THEOBROMINE/3~7-OIMETHYLXANTHINE/ THEOPHYLLlNEIlr3-OIMETHYLXANTHlNEl THEOPHYLLINE/lr3-OIHETHYLXANTHINE/ THEOPHYLLINE/1~3-OIMETHYLXANTHINE/ THEOPHVLLINE/lr3-OIMETHYLXANTHINE/ THEOPHYLLINE/lr3-DIMETHYLXANTHINE/ THEOPHYLLINE/lr3-DIMETHYLXANTHINE/ ANISOLE ANISOLE AN ISOL E ANISOLE BENZYL ALCOHOL BENZYL ALCJHOL BENZYL ALCOHOL H- MET~YLPMENOL /CRE SOL I H-METHYLPHENOL /CRESOL I H-METHYLPdENOLICRESOLI H-METHYLPHENOL/CRESOL/ H-HETdYLPHEhOL /CRES3L / M-HETHVLPHENOL/CRESOL/ H-HETHYLPHENOLICRESJLI H-METHYLPHENOL /CRESOL/ H-METHYLPHENJL / C R E S'JL/ M-METHYLPHENOL /CRESOL/ H-HETHYLPrlEkOL/CRESOLI M-HETHYLPHEhOL /CRE S3L I H-HETdYLPnENOL /CRESOL/ M-METHYLPHENOL /CRESOL / H-METHYLPHE~~L/CRES~L/ 0-METHYLPHENOL 0-METHYLPHENOL 0-METHYLPHENOL 0-METPIYLPHENOL 0-METHYLPHENOL 0-METHYLPHEhOL 0- HE T H VL Prl EN OL 0-METHYLPHENOL 0-HETHYLPhENOL 0-HETdYLPHENOL 0-METHYLPHENOL P- M T H Y L Ph ENOL E P-METHYLPHENOL P-METHYLPHENOL P-METHYLPHENOL P-METHVLPHEhOL P- METHYL PHENOL P-ME T H Y L PH ENOL P-MET HY L PHENOL P-HETdYLPrlEkOL BENZENE, l r 2-OIHYOROXY, 4-METHYL BENZE~EI1,2-DIHYOROXY~ 4-HElHYL BEkZENEt 1.2-OIHVOROXV~4-METhYL M-hYOROXY8ENZYL ALCOHOL P-HV OROXY BENZYL ALCOHOL 0-HYOROXY8ENZYLALCOHOL H-HETHOXYPHENOL H-METHOXYPHENOL O-METHOXYPdENOL/GUAI ACOL I 0-METHOXYPHENOL/GUAIACOL/ 0-METHOXYPdEhOLIGUAIACOL/ 0-METHOXYPdENOLIGlJAIACOLI 0-HETHOXYPHENOL/GUAIACOL/ P-HETHOXYPHENOL P-HETHOXVPrlEhOL P-HETHOXYPHEhOL P-METHOXYPHENOL SULFON E t HETHYLPHENYL SULFONE, METHYLPHENYL THIOPHENE.2-CARBOXYLIC ACIOt ETHYL ESTER FUROIC ACID, ETHYL ESTER BENZENESULFONIC ACID. METHYL ESTER BENZENESULFONIC A C I O t METHYL ESTER METHYL TH IOEENZ EN E M-HETHYLPHENYLBORONIC ACID 0-HETHVLPHENVLSORONIC ACID P-HETHYLPHENYLSORONIC A C I O P-METHYLTHIOPHENVL8ORONIC ACID P-HETHOXVPHEhVL8ORONIC ACID N1-METHYLN I C 0 1 INAM IDE CHLORIDE AN I L I N E t N-METHYL AN I L I N E I N-METHYL AN1LINE.N-METHYL BENZYL AMINE BENZYLAMINE BENZYL AH INE BENZYL AMINE BENZVLAHINE BENZYL AMINE BENZYLAMINE BENZYLAMINE BENZYL AMINE 2, 6-LUTIDINE W-TOLUIOINE H-TOLUIDINE M-TOLU I DINE
NO.
SOLVENT
REF FOOT NOTE 314 314 313 72 314 310 314 3 14 312
LDGP SOLV
LOGP OCT 1.59 8 1-60 B 1.43 8
EMPIRICAL FORMULA C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9N1 C7H9Nl C7H9N1 C7H9N101 C7H9N101 C7H9N10 1 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N101 C7H9N10 1 C7H9N 1 0 1 C7H9N101 C7H9N102S1 C7H9N102Sl
NAME H-TOLU I DI N E H-TOLU I D I N E H-TOLUIDINE H-TOLUIDINE H-TOLUIDINE H-TOLUIDINE H- TOLU I DINE H-TOLUIDINE 0-TOLUIDINE 0-TOLUIDINE 0-TOLUIDINE 0- TOLU I D I N E 0-TOLUIOINE OyTOLUIOINE 0-TOLUIOINE 0-TOLU I D I N E 0- TOLU 1 0 1NE 0-TOLUIDINE 0-TOLU I D I N E P-TOLUI DINE P-TOLUIDINE P-TOLUIOINE P-TOLUIDINE P-TOLU I DINE P-TOLU I DINE P-TOLUIOINE P-TOLUIDINE P-TOLUIDINE P-TOLU I O I N E P-TOLiJIOINE P-TOLU 1D I N E P-TOL U 10 I NE P-TOLUIOINE P-TOLU IO1 hE P-TOLU 1DINE P-TOLUI DINE P-TOLUIDINE P-TOLUIDINE P-TOLUIDINE M- AM Ilv OBENZYL ALCOHOL H-METHOXYANILINEIM-ANlSIDINEl H-HETHOXYAN I L INEIM-AN I S IO1 NE I
2 4 0 1 CYCLOHEXANE 2 4 0 2 BENZENE 2 4 0 3 BENZENE 2 4 0 4 BENZENE 2 4 0 5 CCL4 2 4 0 6 N-HEPTANE 2 4 0 7 N-HEPTANE 2 4 0 8 OCTANE 2 4 0 9 OCTANOL 2 4 1 0 OCTANOL 2 4 1 1 CYCLOHEXANE 2 4 1 2 .CVCLDHEXANE 2413 BEN2 EN E 2 4 14 BENZENE 2 4 1 5 CCL4 2 4 1 6 N-HEPTANE 2 4 1 7 N-HEPTANE 2 4 1 8 OCTANE 2 4 19 HEXAOECANE 2 4 2 0 OCTANOL 2 4 2 1 OCTANOL 2 4 2 2 CYCLOHEXANE 2 4 2 3 CYCLOHEXANE 2 4 2 4 CHCL3 2 4 2 5 BENZENE 2 4 2 6 BENZENE 2 4 2 7 BENZENE 2 4 2 8 BENZENE 2 4 2 9 CCL4 24 3 0 CCL4 2 4 2 1 N-HEPTANE 2 4 3 2 N-HEPTANE 2 4 3 3 N-HEPTANE 2 4 3 4 HEXANE HEXANE 2435 2 4 3 6 OCTANE 2 4 3 7 PARAFFINS 2 4 3 8 HEXAOECANE 24 39 DECANE 2 4 4 0 OCTANOL 2 4 4 1 OCTANOL 2 4 4 2 OCTANOL 2 4 4 3 CYCLOHEXANE BENZENE 2444 2 4 4 5 CCL4 2 4 4 6 N-HEPTANE 2 4 4 7 HEXAOECANE 2 4 4 8 OCTANOL 2 4 4 9 CYCLOHEXANE BENZENE 2 4 50 2 4 5 1 CCL4 2 4 5 2 N-HEPTANE 2 4 5 3 HEXAOECANE 2 4 5 4 OCTANOL 2 4 5 5 CYCLOHEXANE 2 4 5 6 BENZENE 2 4 5 7 BENZENE 2 4 5 8 CCL4 2 4 5 9 N-HEPTANE 2 4 6 0 HEX A 0 EC AN E 2 4 6 1 DIETHYL ETI-ER 2 4 6 2 CHCL3 2 4 4 3 OCTANOL 2 4 6 4 CHCL3 2 4 6 5 OCTANOL 2466 CHCL3 2 4 6 7 OCTANOL 2 4 6 8 CHCL3 2 4 6 9 OCTANOL 2 4 7 0 CHCL3 2 4 7 1 DIETHYL ETI-ER 2 4 7 2 CHCL3 2 4 7 3 01 ETHYL E T F E R 2 4 7 4 CHCL3 2475 CHCL3 2 4 7 6 BENZENE 2 4 7 7 OCTANOL 2 4 1 8 OCTANOL 2 4 7 9 OCTANOL 2 4 8 0 CHCL3 2 4 8 1 OCTANOL DIETHYL ETHER 2482 2 4 0 3 CHCL3 2 4 0 4 CHCL3 BENZENE 2405 I-PENT. ACETATE 2486 2 4 8 7 CCL4 2 4 8 8 N-BUTANOL 2 4 0 9 ETHYL ACETATE 2 4 9 0 CYCLOHEXANONE 2 4 9 1 2- BUT ANON E 2 4 9 2 M E - I-BUT .I( TON E 2 4 9 3 OCTANOL 2 4 9 4 CHCL3 2495 HEXANE 2 4 9 6 ETHYL ACETATE 2 4 9 7 CHCL3 2 4 9 8 OCTANOL 2 4 9 9 OCTANOL 2500 OCTANOL
0.58
1.50 1.51 1.28 1.15 0.54 0.45 0.35 1.29 1.32
301
337 314 314 72 314
1.29 1.32 1.61 1.31
8 8
0.67 0.61
1.53 1.13 1.18 0.55 0.47
310
314 314 314
03 .7
0.38 1.39 1.41 0.58 0.55 1.99 1.43 1.49
1.39 1.41 1.43 1.54 1.58 1.52 1.73 1.07
10 301
337 3 14 2 54 314 313 72 375 329 314 310 254 3 14 314 375 314 316 314 3 14 10 312 10 314 314 314 314 314 312 314 314 314 314 314 312 314 314
= =
8 8 8 8 8 8
13 .8
1.70 1.14
1.11
0.48 0.51 0.44 0.41 0.54 0.33 0.30 0.36 0.37 -0.05 0.93 0.93 -0.13 1.12 0.63 -0.28
-0.05 0.93 0.93 1.32
=
=
8
M-METHOXYANILINEIM-ANISIOINEI
H-HETHOXYAN I L I k E I M - A h 1 S I O I N E I H-HETrlOXVAlvIL INEIM-Ah IS I O I h E I H-METHOXVANILIhEIH-4NISIOINEI H-METHOXYANIL I h E / M - A N I S I O I h E / 0-METHOXYANIL I h E I O - A N I S I O I N E / 0-METHOXYANIL I N E I O - A N I S I O I N E I 0-HETHCXVAN I L I N E I O - A N I S I O I N E I 0-HETHOXYANILINEIO-ANISIOINE/
-0.33
0.95 0.52 1.59 1.22 0.39 0.95 1.65
B
=
0.33
0.95 -0.41 0.87 0.78 0.38 -0.54 -0.54 0.80 1.31 0.85 0.32 0.95 1.15 8 1-09 B
0-METHOXYANILINE/O-ANISIOINE/ 0-METHOXYPhILINEIO-ANISIOIhE/
P-METHOXYANIL I N E / P - A h I S I O I N E I P-METnOXYANILINE/P-ANISIOIlvE/ P-METHOXYAN I L INE/P-Ah 1 SI DINE I P-METflOXYANIL I N E I P - A N I S I O I Y E I P-HETHOXVANIL I N E I P - P h I S I O I h E I P-METHOXYANILINEIP-AYISIDIhEI P-METHOXYANIL INEIP-AN I S I O I N E I BkhZENESULFONAHIOEvN-METHYL
BENZE~ESULFONbYIOEth-METHYL H-METHYLBENLEYESJLF9NAMIOE M-METrlYL8EkZEhESULFONbMIOE 0-METHYL 8 E Y Z Eh ESJL FONAH I DE 0-METHVLBENZ Eh ESUL FONAH I O E P-METHYLBE~ZElvESULFJNbYISE P-METHYL8EYZENESULFOhAMIOE P-METHOXYdEhZENESULFO\AMIi3E P-METHOXYBENZENESULFONAMIOE SULFATHIOCARBAMIOE SULFATHIOCARBAHIOE SULFACARSAM IO SULF A t AilBbMIOE 6-DIMETHYLAM INOPUR IrJE PdEhYL BOROV I C AC IO. 3-AMI h O .4-ME THYL
72
314 314 314 113 113 217 217 217 2 17 217 217 217 217 113 113 113 113
08 .1
1.84 0.85 0.85 0.84 0.96
A N
07 07 07 07 07 07 07 07
= = =
N N N C7H9NlOZSl C7H9N102S1 C7H9N102Sl C7H9N103S1 C7H9N10351 C7H9N302S2 C7H9N302SZ C7H9N30351 C7H9N303S1 C7H9N5 C7H1081N102 C7H10N2 t7H10N2 C7HlONZOZSl C7HlONZOZS 1
0.84
0.46
0.82
0.33 0.47 0.15 0.37 -0.78 -1.25
08 .2
0.86 0.47 0.70 0.44
=
N A N A N
-0.12
-0.98 -1.41 -0.24 0.39
15 6 60
-2.16
-0.14
322
311 341 341 217 217 56 113 343 113 343 343 343 194 194 194 194 194 348
B
= =
=
N
-1.83
0.39
N-HETHYL-3-PYRIOYLMETHYLAMINE
3-PYRI OYLETHYLAM INE P-METHYL4MINOBENZENESULFONAHIOE P-HETHYLAMINOBENZENESULFONAMIOE SULFAGUANIOINE SULF AGUAN IO INE SULFAGUANIDINE SULFAGUANIDINE SU LFAGUANID I N E SULFAGUANIDINE SULFAGUANIDINE 8-CARBOXYAOIPIC ACID 8- CARBOXYAOI P I C AC I D 8-CARBOXYAUIPIC ACID 8-CARBOXYAOIPIC ACID 8-CARBOXYAOIPIC ACID N-ACETYLCYCLOBUTANECAR8OXAMIOE AC ETVL PROL I NE N-METHYLCARBAMIC A C I 0 ~ 2 ~ 3 - O I H Y O R O - 2 - M E F U R A N Y L ESTER GLUT AM I C A t 101L N-ACETYL CY CLOHEPTANEOION E 0 I O X IME 3-METHIO-4-AMINO-6-I-PR1,214-TR I A Z INE-5-ONE 3-METHIO-4-AMINO-6-N-PR-1~2~4-TRIAZINE-5-0NE 3-METHOXY-4-AM INO-6-I-PR- 192.4-TRI A2 INE-5-ONE
60 32
32
-0.11
0.08 -0.59 -1.22
4.11
0.08 0.03 -1.22 -1.47 -1.26 -2.38 -0.47 -1.75 -3.37 -0.46 -0.62
-2.61
B
N N
8
2 12 2 2
2
-2.00
-3.20
-1.47 -1.52 -3.00 0.07 -0.50
0.13
67
376 67 265 134 134 134
0.00 -0.83 -0.40 -1.18 -0.59 -1.36 -0.70 1.01 0.93
-0.68
-2.35
-0.40 =
-1.52 -0.05 1.01 0.93
= =
-0.06
-0.06
C7HlON402S1 C7HlONCOZSl C7H1006 C7H1006 C7H1006 C7H 1 0 0 6 C7H1006 C7HIlNlOZ C 7 H l l N103 C7H11N 103 C7H 11N105 C7H12N202 C7H 12 N401S 1 C7H12N401S1 C7H12N402

REF FOOT NOTE 255 LOGP SOLV LOGP OCT 1.50 EMPIRICAL FORMULA NAME
A. Leo, C. Hansch, and D. Elkinr
NO. 2501 2502 2503 2504 2505 2506 2507 2508 2509 25 1 0 2511 2512 2513 2514 2515 2516 2517 2518 25 1 9 2520 2521 2522 2523 2524 2525 2526 2527 2528 2529 2530 2531 2532 2533 2534 2535 2536 2537 2538 2539 2540 2541 2542 2543 2544 2545 2546 2547 2548 2549 2550 2551 2552 2553 2554 2555 2556 2557 2558 2559 2560 2561 2562 2563 2564 2565 2566 2567 2568 2569 2570 2571 2572 2573 2574 2575 2576 2577 2578 2579 2580 2581 2582 2583 25e4 2585 2586 2587 2588 2589 2590 2591 2592 2593 2594 2595 2596 2597 2598 2599 2600
SOLVENT OCTANOL DIETHYL ETkER I-BUTANOL DIETHYL ETHER OIETHYL ETHER DIETHYL ETnER DIETHYL ETkER N-BUTANOL I-BUTANOL ETHYL ACETATE Of ETHYL ETHER OILS OILS OILS 01 ETHYL ETFER I-BUTANOL OILS OLEYL ALCOHOL OCTANOL CHCL3 CHCL3 OCTANOL OCTANOL DIETHYL ETHER PARAFFINS XYLENE OILS OCTANE OOOECANE HEXPOECANE OCTANOL I -BUTANOL OCTANOL CCL4 OILS OILS OILS N-BUTANOL OCTPNOL DIETHYL ETHER OILS OCTANE OOOECANE H EXPOECANE 01 ETHYL ETHER OILS OILS OILS OILS OILS DIETHYL ETFER XYLENE OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE OC TANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CHCL3 BENZENE BENZENE
1.50
1.04 1.22 0.17 0.18 0.14
3
4 2 12 212 207 194 194 4 194 3 2 2 214
1.03
1.21 0.26 0.27 0.24 0.14 0.58 0.70 0.41 -0.46 -0.51 0.14 0.65 -1.90 -2.04 1.66 1.37 0.24
0.04
0.77 0.86 0.43 -0.66 -1.15 -1.15 -0.64 -3.51 -1.09 0.52 .0.81 0.24 -1.48 -1.34
12
3
4 2 96 82 2 60 67 67 2 60 134
3
241 46 220 60
60 60
268 4 227 234 292 292 292 37 7 297 378 201 59 59 59 3 2 2 14 173 224 168 46 46 297 298 206 379 379 206 206 206 206 379 379 206 206 379 379 379 206 206 206 206 379 206 379 319 206 206 379
47 47 47
12
46 44
1.00 0.30 -1.92 -1.02 1.24 1.69 -0.13 -0.18 -0.29 -0.17 -1.41 0.63 0.32 -0.38 -0.59 -0.81 -0.77 -0.25 -1.03 1.34 0.93 0.86 0.17 -0.07 -0.96
10 .0
0.30 -0.82
3.13 2.72
-0.17 -2.48
0.63
0.84 0.65 0.45 -1.59 -0.25 0.04 2.41
0.05
0.37 0.48 0.58 0.98 0.52 2.02 2.09 -2.60 4.20 4.81 3.97 4.08 3.78 3.87 4.15 3.21
0.05
0.18 0.65 0.10 1.30 1.34 -2.60 4.20 4.81 -0.26 0.94 3.97 4.08 3.78 3.87 0.57 0.42 4.15 3.21 -0.74 -0.06 0.37 2.87 3.49 3.49 3.99 0.30 3.89 -1.10 -0.82 3.57 3.39
46 19 19
19 19
19 19 19
2.87 3.49 3.49 3.99 3.89
19 19 19 19
3.57
3.39 2.93 4.62 2.68 3.34 2.23
-0.31
2.93 4.62 2.68 -1.70 -0.10 3.34
206
2 35 206 379 379 218 141 141 141 141 141 141 141 141 141 206 379 10 279 3 80 279
19
19
16 .6
2.23 1.49 2.53 2.68 2.76 3.12 0.31 0.87 2.67 -0.95 2.95 1.73
2.67 2.95 2.79 2.95 2.96
19
16 .0
1.62
C7ti1201 C7HlZO4 C7H1204 A C7Hl204 A C7H1204 A C7H1204 A C7H1204 C7H1204 C7H12D4 C7H1204 A C7H1205 8 C7H1205 A C7H1205 A C7H1205 8 C7H1206 C7Hl206 A C7H138RlN202 C7H138RlN202 = C7H13N101 C7H13N103 C7H13N10351 = C7H13NlSl C7H13N501 8 C7H14N202 C7H14N2Sl A C7H1402 A C7H1402 C7H1402 C7H1402 C7H1402 = C7H1404 C7H1406 = C7H15CLZN202Pl C7H15N101 A C7H15N101 A C7H15N101 A C7H 15N 1 0 2 C7HlbCLlNlO2 = C7H16N102 8 C7H16N202 A C7H1601 C7H1601 C7H1601 C7H1601 A C7H1603 A C7H1603 8 C7H 160452 8 C7H1604S2 8 C 7H 160 4 S 2 B C7H 1 6 0 4 5 2 8 C7H 17 N 1 B C7H17N1 C7H1811N1 = C7H18SI1 = CBHlBR4F3N2 C8H 1 L 2 F 3 N404 C C8HICL4F3NZ = CBHlCLCF3N2 = C8H28R3F3N2 = C8H2CL3F3N2 = C8H2CL3F3N2 CBHZCL3F3hZ CBHZCL3F3N2 = C8H3BR2F3N2 = CBH3tLlF3N302 C8H3CLlF3N302 CBH3CLlF3N302 C8H3CLlF3N302 = C8H3tLZF3N2 = C8H3CL2F3N2 = C8H3CL2F3N2 = CBH3CL2F3N2 C8H3CL2F3N2 = C8H3F3N404 CBH3F3N404 C8H 3F3N404 = CBH48RlF3N2 = CBH4CL1F3N2 C8HCCLlF3N2 = CBHCCLlF3N2 = CBH4CL6 = CBH4F3N302 C8H4F3N302 C8H4F3N302 = C8H58RlF3N101 C8H58RlN204 = C8H5CLlN204 CBH5CLlN204 CBH5CL2N102 CBH5CL2N102 C8H5CL2N102 CBHSCLZN102 CBH5FlN204 CBHSFlN204 = CBHSF3N2 C8H5F3N2 = CBH5F302 A CBH5F302Sl A C8HSF30251 A CBH5F302Sl
~-BUTANONEI~-CYCLOPROPYL 01ETHYLHALONIC ACID DIETHYLMALONIC ACID P I M E L I C ACID P I M E L I C ACID P I M E L I C ACID P I M E L I C ACID P I M E L I C ACID P I M E L I C ACID PIMELIC ACIO GLYCERYL OIACETATE GLYCERYL OIACETATE GLYCERYL OIACETATE GLYCERYL OIACETATE CYCLOHEXANECARBOXYLIC AC1Oilr3r4r5-TETRAHYOROXY/OUINlC/ CY CLOHEXANECARBOXYL I C A C I O i 1 - 3 9 4rS-TETRAHYOROXY/OUI N I C / A-8ROMO-A-ETHYLBUTYRLUREA/CARBROMAL/ A-BROMO-A-ETHYLBUTYRLUREA/CARBROHAL/ 2-AZACYCLOOCTANONE L-VALINE, ACETYL L-METHIONINEIACETYL 2-AZACYCLOOCTANTHIONE 6-I-PROPYL-4-AHINO-3-MEAHINO-lrZ14-TRlAZIN~5~ONE 01 ETHYLMALONIC ACID DIAMIDE N-BUTYLETHYLENETHIOUREA I-AMYLACETIC ACID HEPTANOIC ACID HEPTANOIC ACID HEPTANOIC ACID HEPTANOIC ACID GLYCERYLMONO8UTYRATE/8UTYR I N / A- ME THY LGL UCOS I O E
CYTOXAN/CYCLOPHOSPHAHIOE/
01 THY L PROP ION AM I DE N 9 N- 0 I HE THY L VAL ER AH I OE N-ETHYLVALERAM I O E N t N-OIETHYLLACTAMlOE ACETYLCHOLINE CHLOR IOE AC ETYLCHOL I N E CATION CAR8 AH I C AC 10, N, N-0 I ETHYL AH I NOETHY L E S T E R HEPTANOL HEPTANOL HEPTANOL HE PT ANOi GLYCEROL. l r 3 - O I E T H Y L ETHER GLYCEROL, 1.3-OIETHYL ETHER 2.2-8IS(ETHYLSULFONYL PROPANE /SULFONAL/ 2 , 2 - 8 1 S ( ETHYLSULFONYL JPROPANElSULFONALl 2,2-815 (ETMYLSUL FONYL J PROPANE/SULFOhAL/ 2.2-81 S(ETHYLSULF0NYL 1 PROPANE/SULFONAL/ HEPTYLAYINE HEPTYLAMINE T R IYETHYLBJTVLAMMONIUM I O D I D E SILANE, BJTYL-TRIYETHYL BENZIMIOAZOLE~4~ 6~7-TETRA8ROMO-2-TRIFLUOROMETHYL 5r BEN2 I M IDAZOL E. 2-TR IFLME-4r 6-0ICL-Sr 7-01 N I T R O BENZIM ICAZOLEI 41 5,6971 ETRACHLORO-2-TRI FLUOROME B E N 1 I H I DAZOLEv 49 5 9 6 , 7-TETRACHLORO-2-TRI FLUOROMETHYL BEhZIMIOAZOLE, 49 5 1 6 - T R IBROMO-2-TRIFLUOROHE THYL BEhZ I M I O A Z O L E ~ 5 # 7 - T R ICHLORO-2-TRIFLUOROMETHYL 4r 8E hZ 14 10AZT)LE t 4r 5.6-TR I CHLORO- 2- TR I F LUOROME THY L 8ENZIY I D A L J L E ~ 51 6 - T R ICHLORO-2-TRIFLUOROMETHYL 49 BE h2 I M l DAZOLEI 2-TR IFLUOROHE-4~6r7-TR ICHLORO 8EhZlMlCAZOLE~2-TRIFLVOROnETHYL-5~6-OI8ROMO 8EN~IHICAZOLE~5-CHLJRO-6-NITRO-2-lRIFLUOROME BEN2 1 M IOAZOLEI 2-TRIFLME-4~CHLORO-6-NI TRO BE h I Y I OALJL E, 2-TR IFLME-6-CHLORO-5-hl T R O Z 8EhZIYIOAZOLE~2-TRIFLME-6-C~LORO-4-hITRO 8EhZ 1 M IOAZOLEI 2-TR I F L u O R O H E - ~ . ~ - O I C H L ~ R O BEhlIHIOAZOLE~2-TRIFLUOROHE-4,5-DIChLORO B E ~ Z ~ M I O A Z O L E I~ T R I F L ~ O R O M E ~ 4 ~ 6 ~ O I C H L O R O 2 BENZIH I D A Z ~ L E I2-TR IFLJOROHE-5,6-DICHLORO BE hZ I M IOAZOLEI 2-TR IFLUOROHE-4~5-OIChLORO h l TRO ~ENZIMIOALOLEI2-TRIFLbOROME-5,6-OI 8Eh2IMIOA~OLE~2-TRIFLUOROHE-5~6-OlNlTRO BEN2 I M IOAZJLEI 2-TR I F L U O R O H E - 4 ~ 6 - O l h I TRO 0Eh2IHlOAZOLE~ 2-TR IFLUOROHE-5-BROHO BE hZ 1 M 1CAZJL E t 2-TR IFLUOROME- 5-CMLORO BEhZIYIOALOLE~2-TRIFLUOROME-5-ChLORC
8ENZIHtOAZOLE~2-TRIFLUROHE-4-CHLORO P-31(TRICHLOROMETHYL)BENZEYE BEN2 I M I CALOLE 9 2-TR IFLUOROME-5-N I TRO 8EhZ I M I JAZOL E t 2-TR I F L UOROYE-5-NI TRO 8EhZIMICAZOLE12-TRIFLUOROME-4-hlTR0 ~ROHOBENZE~EIP-TRIFLuOROACETAMIOO
STVRE~EI~-~ROMOI 5-NITROIR-hITRO S T YREhE 2-C hLORO- 5-N I TRO- 8 - N I T R O

STYREYE~Z-ChLJR0.5-YITROIB-hITRO
S T Y R E ~ E I2~L-OICHLORO-8-hITRO STYRENE, 3 r 4 - O I C H L O ~ O ~ 8 - h l T R 0
STVRihit2~4-OICHLORO.8-hlTRO STYRENE,2~6-OIChL0~3~8-NlTRO S T Y R E k 9 4-FLJOROv 3-N1 T R O I 0-NITRO STYRENE,~-FLUOROI~-NITRO~~-~ITRO 0EhZIMIOAZOLE~Z-TRIFLJ~ROHETHYL 8EhZIMIOAZ~LE~2-TRIFLUOROMETHYL M - T R I F L ~ O R O M E T ~ V L 8 E Y L O l C ACID THENOVL-TRIFLUOROACETGYE
THEhOVL-TR I FLJOROACETONE
TMthOYL-T91FLUOROAC~TJhE
NO.
2601 2602 2603 26C4 2605 2606 26C7 26C8 2609 2610 2611 2612 2613 26 1 4 2615 2 6 16 2617 2618 2619 2620 2621 2622 2623 2624 2625 2626 2627 2628 2629 2630 2631 2632 2633 26 34 2635 2636 2637 2638 2639 2640 2641 2642 2643 2644 2645 2646 2647 2648 2649 2650 2651 2652 2653 2654 2655 2656 2657 26 58 26 59 2660 2661 2662 2663 2664 2665 2666 2667 2668 2669 2670 2671 2672 2673 2674 2675 2676 2677 2678 2679 2680 2681 2682 2683 2684 2685 2686 2687 2688 2689 2690 2691 2692 2693 2694 2695 2696 2697 2698 2699 2700
SOLVENT CCL4 HEXAN6 0-OICL. BENZENE XYLENE TOLUENE OCTANOL O C 1ANOL 0.1ETHYL E T C E R CHCL3 OC TANOL DIETHYL E T C E R CYCLOHEXANE CHCL3 OILS OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OC TANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OILS OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OILS 0 1 ETHYL ETHER OILS OILS OCTANOL DIETHYL E T C E R 0 1 ETHYL ETHER 0 1 ETHYL E T C E R OIETHVL E T C E R I BUTANOL XYLENE ME- I-8UT.K TON E S-PENTANOLS CHCL3 OCT~NOL OCTANOL OILS OCTANOL OCTANOL OILS 0 CT ANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE OILS OCTANOL OCTANOL OILS OCTANOL
REF F o o l NOTE 279 279 2 79 279 2 79 10 10 113 113 9 113 304 113 381 255 302 309 141 141 141 302 302 141 141 141 141 141 141
LOGP SOLV 1.30 0.68 1.59 1.58 1.60 1.48 1.56 0.31 0.23 1.15 1.03 -1.46 1.08 0.55 2.53 2.75 3.00
LOGP OCT 2.54 N
EMPIRICAL FORMULA C8H5F302Sl C8H5F302Sl C8H5F302Sl CBH5F30251 C8HSF302Sl C8H5N102 CBH5N102 CBHSNlO2 CBH5N102 CBH5N102 CBH5N102 C8H5N102 C8H5N102 C8H5NlO2 C8H6 C8HbBRlCL103 C8H6BRlN1 CBH68RlNlO2 C8H68RlNlOZ C8H68RlN102 C8HbCLlF103 C8HbCLlI103 C8HbCLlN102 CBH6CLlN102 C8H6CLlN102 C8H6CLlN102 CBH6CLlN102 CBHbCLlNlOZ
NAME THENOYLTRIFLUOROACETONE THENOYLTRI FLUOROAC ETONE THENOYLTRI FLUOROACETON E THEONVLTRIFLUOROACETONE TH EONYLTRI FLUOR0 ACETON E H-CVANOBENZOIC ACID P-CYANOBENZOIC ACID INOOLEt 2 ~ 3 - O I O N E / I S 4 T I N / INOOLEI 2 ~ 3 - O I O N E / I S A T I N / PHTHAL I I DE H PHTHALIMIDE PHTHALIMIDE PHTHAL I M I DE PHTHALIHIOE BENZENE, ETHYNYL PHENOXYACET I C ACIO~3-8ROMO-4-CHLORO INDOLEI 5-BROMO STYRENEv 4-BROMO. 8-NITRO STYRENE, 2-BROMO1 8-NITRO STYRENE, 3-BROMO1 8-NITRO PHENOXYACET I C A C 10~3-CHLORD-5-FLU3RO PHENOXY A C E T I C A C I O t 4- CHLOR 0- 3- I 0 0 0 S T V R EN E v 4-C HL ORO- 8-N I TRO STYRENE, 3-CHLORO-B-NI TRO STYRENE, 2-CHLORO-8-NITRO S T YRENEt 4-CHLORO t 8-N I R O T STYRENE, 3-CHLORO, 8-N1,TRO STYRENE, 2-CHLORO, 8-N1 TRO PH EN O X Y ACE T I C AC IO 4-CHLORO- 3-N I TRO PHENOXY ACE1 I C A t 1 0 9 2 1 4 - 0 ICHLORO PHENOXYACETIC ACIO~3r4-OICHLORO PHENOXYACETIC AC 101 5-FLUORO- 3- I 0 0 0 STYRENE, $-FLUOR01 8-N 1 T R O v STYRENE, 3-FLUOROq B-NITRO STVREN E t ~-FLUOROIB-NITRO BENZOIC A C I 0 ~ 4 - O H ~ 3 ~ 5 - O I - I O O O t n E T H Y LESTER PUINOXALINE TRO-8-N I T R O STYRENE 1 2-N I STYRENE, 3-NITRO-8-NITRO STYRENE, 4-N ITRO-8-N I T R O S T V R E N E ~ ~ - N I T R O8-NITRO I STYRENEI~-NITRO,B-NITRO STYRENE~3-NITRO~8-NITRO l - M E T H Y L - 5 ~ 7 - 0 1 N ITROBENZPVRAZOLE BENZOFURAN 0-TOLUIC ACID LACTOYE/PHTHALIDE/ BENZOYLFORHIC ACID PIPERONAL P I PERONAL M-PHTHALIC ACID M-PHTHAL I C A C I O 0-PHTHALIC ACID 0-PHTHALIC ACID 0-PHTHALIC ACID 0-PHTHALIC ACID 0-PHTHALIC ACID 0-PHTHALIC ACID 0-PHTHALIC ACID PIPERONYLIC ACID BENZOTHIOPHENEI(BI BENZOTHIOPHENEI(~I BROMOACETOPHENONE M-BROMOPHENYLACETIC ACID P-BROMOPHENYLACETIC ACID P-BROMOPHENYLACETIC A C I O PHENOXYACETIC ACI0.2-BROMO PHENOXVACETIC AC 10.3-BROMO PHENOXVACETIC ACIO.4-8ROMO BENZIMIOAZOLEv 5-CHLORO-2-(METHYLTHIOI CHLOROAC ETEPHENONE CHLOROACETOPHENONE H-CHLOROPHENYL ACE1 I C A C I O P-CHLOROPHENYLACETIC ACID P-CHLOROPHENVLACET I C ACID PHENOXYACETIC ACI0.M-CHLORO PHENOXYACETIC ACIO.M-CHLOR0 PHENOXVACETIC ACI0.M-CHLORO PHENOXYACETIC ACt0.M-CHLORO P,HENOXYACETIC ACI0,O-CHLORO PHENOXVACETIC ACI0.P-CHLORO N-METHYL-3s 4 - O I C K O R O P H E N V L C A R B A M A T E N-METHYL-3r 5-OICHLOROPHENVLCARBAHATE M-FLUOROPHENVLACETIC ACID 0-FLUOROPHENYLACETIC ACID P-FLUOROPHENYLACETIC ACID PHENOXVACE1 I C AC IO* M- FL UORO PHENOXY ACE1 I C AC ID.0-FLUOR0 PHENOXYACET I C A I0;P-FLUOR0 C PHENOXVACETIC AC I0.P-FLUOR0 P-FLUOROSULFOYVLPHENVL ACE1 I C AC IO P-FLUOROSUL FONVLPHENO XVACE T I C AC ID PHENOXVACET I C AC IO, 3-P ENTAFLUOROTH I10 H-IOOOPHENYLACETIC ACID P-IOOOPHENYLACETIC ACID P-IODOPHENVLACETIC ACID PHENOXYACE1 I C AC IO 9 2- I O D 0 PHENOXYACETIC A C I O ~ 3 - I O D O PHENOXVACETIC A C I O I + I O W INWLE INDOLE
2.98
1.48 1.56 1.12
= =
B
0.80
1.15 1.02 1.60 1.69 2.53 2.75 3.00
=
A
N
A
=
= =
2.33
2.44 2.48 2.20 3.10 2.44 2.57 2.85 2.24 2.33 2.20 3.10 2.44 2.57 2.85
=
=
=
=
2.52
1.85 2.81
302
10 218 302 141 141 141 382 360 141 141 141 141 141 141 276 218 224 207 173 224 10 212 212 207 46 4 46 195 195 46
2.81
2.42 1.61 1.74 1.94 3.55 0.84 1.80 1.82 1.89 0.72 0.89 1.01 1.63 2.67 0.52 0. 80 1.47 2.00 1.66 1.46 0.20 0.10 0.28 0.86 -1.55 0.44
1.85 2.81 2.81 2.42
= = =
=
CBHbFlN102 C8H6FlN102 C8H61203 C8H6N2 C8H6N204 C8H6N204 C8H6N204 C8H6N204 C8H6N204 C8HbN204 C8HbN404 C8H601 C8H602 CBH603 C8H603 C8H603 C8H604 C8H604 C8H604 C8Hb64 C8H604 C8H604 C8H604 C8H604 C8H604 CBH604 C8H6S1 C8HbSl C8H7 B R I O 1 C8H7BR102 C8H78R102 C8H78R102 CBH7BR103 C8H78R103 C8H7BR103 C8H7CLlN251 C8H7CL101 C8H7CL101 CBH7CL102 C8H7CL102 C8H7CL102 C8H7CLlO3 CBH7CL103 CBH7CL103 CBH7CL103 CBH7CL103 C8H7CL103 CBH7CL2N102 CBH7CLZN102 C8H7F102 CBH7FlOZ C8H7F102 C8H7F103 C8H7F103 CBH7F 1 0 3 C8H7F103 CBHIF10451 CBH7F10551 C8H7F503S I C8H71102 C8H7 I 10 2 C8H7I1 0 2 C8H71103 C8H71103 C8H71103 C8H7N1 C8H7N1
4.42 0.84 1.80 1.82 1.89
=
= = =
1.63 2.67 0.88
=
= 8
A 8
0.82
1.61 1.66 1.39 0.29
02 .0
0.37 0.70 0.10 0.41 0.38 1.85 3.12 3.09 2.29 2.37 2.31
7 A A A A
A A
0.60
0.70
218
309 173 10 10 3 83 10 10 10 206 304 173 10
3.12
3.09 2.24 2.37 2.31 1.86 2.10 2.22 2.45 3.22 1.44 1.99 2.09 2.12 1.38
=
=
B
= =
A
2.88
2.10 2.22 2.45 3.22
= =
= =
B
20 .8
2.09 2.12 2.48
10
3 83
= =
A
HE- I-BU T .K TONE CYCLOHEXANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OILS OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL
CYCLOHEXANONE
10
2.03
3.00 2.32 2.46
2.03
302 302 302

10
2.02
1.99 2.80 3.03 1.65 1.50 1.55 1.48 1.26 1.41 1.82 1.86 1.82 2.78 2.62 2.64 1.63 2.19 2.44 2.69 2.00 2.14
10
384 38 4 10
10
10
10 10 10
302 65 65 10 10
2.02 1.99 2.80 3.03 1.65 1.50 1.55 1.48 1.26 1.41 1.86 1.82 2.78 2.62 2.64 2.72 2.19 2.44 2.69 2.00 2.14
= = = = = = = =
= =
= = = =
10
383
10
10
10
276 186
-=

NO. 2701 2702 2703 2704 27C5 2706 27C7 27C8 2709 2710 2711 2712 2713 2714 2715 2716 2717 2718 2719 2720 2721 2722 2723 27 24 2725 2726 2727 2728 2729, 2730 2731 2732 2733 2734 2735 2736 2737 2738 2739 2740 2741 2742 2743 2744 2745 2746 2747 2748 2749 2750 2751 2752 2753 2754 2755 2756 27 57 2758 2759 2760 2761 2762 2763 2764 2765 2766 2767 2768 2769 2770 2771 2772 2773 2774 2775 2776 2777 2778 2 17 9 2780 2781 2782 2783 2 7 84 2785 2706 2707 2788 2789 2790 2791 2792 2793 2794 2795 2796 2797 2798 2799 2800 SOLVENT OCTANOL OCTANOL CYCLOHEXANE OCTANOL OCTANOL OCTANOL CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OILS OCTANOL CYCLOHEXANONE ME-I-8UT.KETONE CYCLOHEXANOL OCTANOL OCTPNOL OCTANOL CHCL3 OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OC7ANOL OCTANOL OCTANOL 0 I ETHYL ETC.ER CHCL3 CCL4 CL CHZCHZCL OCTANOL OCTANOL OCTANOL OCTANOL DIETHYL ETCER BENZENE CLCHZCHZCL OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE OCTANOL OC T ANOL DIETHYL ETFER OIETHYL Ell-ER OIETHYL E T k E R CHCL3 OILS OILS OILS BENZENE I-BUTANOL XYLENE TOLUENE TOLUENE NITROBENZENE PRIM. PENTANOLS OCTANOL CYCLOHEXANE CHCL3 TOLUENE OCTANOL CHCL3 TOL U NE OCT ANOL BENZENE CCL4 HEXANE 0-OICL. BENZENE OCTANOL CHCL3 CHCL3 BENZENE BENZENE DIETHYL ETCER OIETHYL ETHER 0 1 ETHYL ETHER DIETHYL ETHER DIETHYL ETHER CYCLOHEXANE CHCL3 OILS OILS BENZENE BENZENE TOLUENE CLCHZCH2CL 01-I-PR. ETnm OCTANOL OCTANOL
~~~~
REF FOOT NOTE 309 255 358 309 56 141 141 10
LOGP SOLV 2.25 1.56 1.56 1.15 2.24 2.11
LOGP OC T 2.25 1.56 1.15 2.24 2.11 1.42 1.49 2.07 2.12 1.45 1.39 1.61 1.37
EMPIRICAL FORMULA CBH7Nl C8H7N1 C8H7N1 C8H7N101 CBH7N102 C8H7N102 C8H7N102 CBH7N103 C8H7N103 C8H7N103 C8H7N103 C8H7N103 C8H7N103 C 8H7N 1 0 4 CBH7N104 CBH7N104 C8H7N105 CBH7N105 C8H7N105 CBH7N105 CBH7N105 CBH7N105 C8H7NlSl C8H7NlS2 C8HBBRlN102 C8HBBRlNlOZ C8HBBRlNlOE C8HBCLlN102 C8H8CLlN102 CBHBCLlNlOZ C8H8CLlN103 CBH8FlNlOZ CBHBFINIOZ C&8F i N l 0 2 CBHBFlN103Sl C8HBIlN104Sl C8H811N104S1 C8HBIlN104Sl C8H811N104S1 C8H8N204 CBH8NZ 0 4 C8H8N204 C8H801 CBHBO1 CBH801 C8H801 C8H801S1 C8H802 C8H802
NAME INDOLE PHENYLACETONITRILE P-TOLUONITRILE O INDOLE X STYRENE, 8-NITRO STYRENE, 8-NITRO STYREN 9 8-NI TRO M- ACET YLNI TROBENZENE T P- A ETY L N I ROB EN ZEN E C STYRENE, 3-HYDROXY-8-N ITRO STYRENE, 4-HYDROXY-&NITRO STYRENE.4-HYDROXY v 8 - N I TRO STYRENEI~-HYOROXYIB-NITRO M-NITROPHENYLACETIC ACID P-NITROPHENYLACETIC ACID P-NITROPHENYLACETIC ACID PHENOXYACETIC ACIOIM-NITRO PHENOXYACETIC ACIOIH-NITRO PHENOXYACETIC ACI0.H-NITRO PHENOXYACETIC ACI0.M-NITRO PHENOXYACETIC ACIOIO-NITRO PHENOXYACETIC ACIOVP-NITRO BENZYL ISOTHIOCYANATE METHYLTHIOBENZOTHl AZOLE N-METHYL-2-BROMOPHENYLCARBAMATE N-METHYL-3-BROMOPHENYLCAR8AMATE N-METHYL-4-BROMOPHENYLCARBAMATE N-METHYL-2-CHLOROPHEN YLCARBAMATE N-METHYL-3-CHLOROPHENYLCARBAMATE N-METHYL-4-CHLOROPHENYLCAR8AMATE PHENOXYACETIC ACIO~3-AMINO-4-CHLORO N-METHYL-2-FLUOROPHENYLCARBAMATE N- ME THY L-3-FLUOROP HENYLCAR BA MA TE N-METHYL-4-FLUOROPHENYLCAR8AMATE
= = * = =
=
18 .0
1.42 1.49 2.07 2.12 -1.60 -1.36 1.45 1.39 0.43 1.37 2.77 1.88 1.93 1.22 1.48 2.83 2.00 1.77 2.25 2.17 1.64 2.03 2.01 1.16 1.25 1.48 1.28 2.17 1.64 -0.20 -2.00 0.32 1.02 1.39 1.47 1.58 1.15 2.20 2.38 2.23 1.49 1.39 35 -2.14 2.12 1.41 1.57 1.33
10
141 141 141 141
10 10
383 10 302 302
=
A
302
10
10
238 322 384 3 84 384 384 38 4 384 302 384 384 3 84 65 306 306 306 306 38 4 3 84 384 10 248 248 248 2 68 10
1.22 1.48 2.83 2.38 1.77 2.25 2.17 1.64 2.03 2.01 1.16 1.25 1.48 1.28 2.17 1.60 0.15 1.02 1.39 1.47 1.58 1.67 2.07 2.23 1.49 1.39 1.35 2.12 1.41 1.49 1.28 1.37 1.63 1.57 1.33 1.42 1.38 1.51 1.38 1.66 1.46 1.42 1.57 2.37 2.83 2.54 2.27 2.91 2.18
= = = = = = = = = = = =
A A
P-ACETAMIOO-BENLENESULFONYLFLUORIOE N-IP-IOOOBENLENESULFONYL JGLYCINE

N- IP-IOOOBENZENESULFONYL JGLYCINE N-IP-IOOOBENZENESULFONYL )GLYCINE N-IP-IOOOBENLENESULFONYL JGLYCINE N- METHYL-2-N ITRO PHENYL CARBAMATE N-METHYL-3-NITROPHENYLCARBAMATE N-METHYL-4-NITROPHENYLCAR8AMATE AC TOPHENON E AC ET OP H ENONE AC TOP b ENONE ACETOPHENONE THlOACETIC ACID, S-PHENYL ESTER ACETIC ACID, PHENYL E S T E R M-ACETYLPHENOL P-ACETYLPHENOL P- AC ETY L PHENOL BENZOIC ACIOPMETHYL ESTER PHENYLACETIC ACID PHENYLACETIC ACID PHENYLACETIC ACID PHENYL ACE1 I C ACID PHENYLACETIC AC I O PHENYLACETIC A t 1 0 PHENYLPCET I C ACID PHENYLACETIC ACI 0 PHENYL ACE1 I C ACI 0 PHENYLACETIC ACID PHENYLACETIC ACID PHENYLACETIC ACID PHENYLACETIC ACID PHENYLACETIC ACID PHENYLACETIC ACID M-TOLUIC ACID 0-TOLUIC ACID 0-TOLUIC ACIO 0-TOLUIC ACID P-TOLUIC ACID P-TOLUIC ACID P-TOLUIC ACID PHENYLTHIO-ACETIC ACID THENOYLACETONE THENOY L ACETON E
10 A .0
12
= = = =
A 8
50
12
= = = = =
10 10
56 10
i.
C8HeOZ
C8H802 C8H802 C8H802 CBH802 C8HBOZ CBH802 CBH802 C8H802 ~811802 C8H802 C8H802 C8H802 C8H802 C8H802 C8H802 C8H802 C8H802 C8HBO2 CBH802 C8H802 C8H802 C8H802 C ~ H ~ O Z CBHBOZ CBH80251 CBH802S1 C8H802Sl CBHBOZS1 C8H802SI C8H8OZSEl C8H802SEl C8H802SEl C8H802SEl t8HBO2SEl CBH803 C8H803 CBH803 CBH803 CBH803 C8H803 CBH803 CBH803 C8H803 C8H803 C8H803 C8H803 CBli8D3 C8H803 C8H803 C8H803
10
3 207 46 29 361 362 385 29 4 46 48 29 48 48 10 357 29 29
1.44
12 0.45 0.35
01 .3
0.26 -0.03 1.43 -0.38 0.09 -0.13 0.67 1.48 2.37 0.65 1.76 1.10 2.27 1.81 0.68 1.91 2.40 2.06 1.30 2.49 2.05 2.92 3.39 3.00 2.92 1.35 0.97 0.91 0.93 0.96 -0.75 1.42 0.42
A A
25
10
29 29 386 279 279 279 279 386 3 87 388 387 388 323 3 323 359 248 248 366 173 224 389 248 389 248 366 186 261
12
1.91
3.70 3.57 2.05 3.89
4.30
=
A
N
A A
THENOYLACETONE
=
A
A A A A A A A A
4.30 4.23 1.30 0.96 0.91 0.94 0.96 1.92
1.58
1.63 2.20 2.21 2.14 1.24 1.05 1.89
04 .8
0.81 0.82 0.64 1.29 0.60 1.05 1.89
N A A A A A
= =
THENOY LACETONE PHENYLSELENO-ACETIC AC I O 1- 12-SELENOPHEN-YL I-li3-8UTANEOIONE 1- 12-SELENOPHEN-YL )-1v3-BUTANEOIONE 1-12-SELENOPHEN-YL I-lr3-BUTANEOIONE 1- 12-5 EL ENOPHEN-YL I - 1 9 3-BUTANE0 IONE BENLALOEHVOE~2-HYOROXY-3-METHOXY/O~VANILLIN/ BENZALOEHYOEI 3 - M E T H O X Y ~ 4 - H Y O R O X Y / V 4 N I L L I N / BENLALOEHYOEt3-METHOXY-4-HYOROXY/VANILLIN/ BENZALOEHYOEI~-~ETHOXY +4-HYOROXY/V4NILLIN/ L L I N/ BENZAL OEHYOEs 3-HETHOXY-4-HYOROXY/VI\NI BEN2 AL OEHY DEI 3-METHOXY-CHYOROXY /VAN1 L L 1N I BENZALOEHYOE~3-METHOXY-4-HYOROXY/VANILLIN/ BENZALOEHYDEI~-METHOXYI~-HYOROXY/V~NILL~N/ BEWALDEHYOEt 3 - M E T H O X V - 4 - H Y O R O X Y / V A N I L L I N/ 8ENZALOEHYOEi3-METHOXYt4-HYOROXY/VANILLIN/ BENZAL DEHYOEv 3-METHOXY-4-HYDROXY/VANILLI N/ BENLALOEHYOEI~-METHOXY~~-HYOROXY/VANILLIN/ BENZALOEHYOEI 3-METHOXY-4-HYOROXY/VANI L L I N/ BENZALDEHVOE~3-METHOXY~CHYDROXY/VANILLIN/ BENZYL ALCOHOLr3.C-METHYLENEOIOXY H-CARBOMETHOXYPHENOL

EW I R I CAI. P
FORMULA
NO. 2801
SOLVENT
REF FOOT
NOTE 261 235 10
LOGP SOLV
LOGP OCT
NAME P-CARBOWETHOXYPHENOL P-HYOROXV8ENZOIC ACIO. METHYL ESTER M-WDROXVPHENVLACETIC ACID 0-HVOROXVPHENVLACETIC ACID P-HVOROXVPHENVLACETIC ACID W-METHOXVBENZOIC ACID 0-METHOXVBENZO I C AC IO O-METHOXV8ENZOIC ACID 0-METHOXV8ENZOIC ACID 0-METHOXVBENZOIC ACID 0-METHOXV8ENZOIC ACIO P-METHOXVBENLOIC A C I O / A N I S I C ACID/ P-METHOXVBENZOIC A C I O / A N I S I C ACID/ P-METHOXVBENZOIC A C I O / A N I S I C AGIO/ P-METHOXVBENZOIC A C I O / A h I S I C ACID/ P-METrlOXVBENZOIC A C I O / A N I S I C A C I O I P-METHOXVBENZOIC ACIOIANISIC ACID/ PHENOXVACETIC ACID PHENOXVACETIC ACID PHELOXVACETIC ACIO PHENOXVACETIC ACID PHENYLACETIC ACIOiA-HVDROXV/MANOELIC ACID/ PHENYLACETIC ACIOIA-HVDROXY/MANOELIC ACID/ PHENYLACETIC ACI0.A-HVOROXV/MANOELIC A C l O/ PHENVL ACE1 IC ACID, A-HYOROXV/MANOELIC ACI O / PHENYLACETIC ACIOIA-HVDROXV/MANDELIC ACIOl PHEhVLACETIC ACIOIA-HVOROXY/MANOELIC ACID/ PHENOXVACET I C ACIOeM-HYDROXY PHENOXYACETIC ACIOIO-HVOROXV PHENOXVACET I C ACIO*P-HYDROXY PHENOXVACETIC ACI0.P-HVOROXV PHENOXVACETI C AC ID, P-HVOROXV PH ENOXV ACET I C AC I O t P-HVORO X Y 8ENZNE~Z-BROMO-l-ETHVL BELZENEt 2-CHLORO-1-ETHYL ACETAN I L IO ACETAN I L I O E ACETANILIDE ACETAN I L I OE ACETAN I L I D E ACETAN I L 1OE ACETAN I L I O E AC TAN I L I DE ACETAN I L I DE ACETAN I L I DE ACE1 AN I L I DE ACETAN I L I O E N-METHYL-SAL ICVL IOENEIMIhE /SCHIFF BASE/ N-METeVL-SALICYLIOINEIMIkE /SCHIFF BASE/ PHENYLACETAHIOE P-AMINO8ENZOIC ACIDIMETHYL ESTER P-AMlhOPHEAVLACETIC ACID ANTdRANILIC A C IOih-METHYL A N T k R A h I L I C ACI0.k-YEThYL 8ENZENEsB-NITROETHYL 1~3-OIMETrlYL-2-NITRO8EhZEkE GLYCIhEv A-PHENYL M-METHOXVBENZAMI OE 0-METHOXVBENZAMIOE P-METrlOXVBENZAMI DE N-HETHYLPHENVLCARBAUATE N-METHVLPHENYLCARBAMATE N-METHVLPHENVLCARBAMATE h I C O T I k I C A C I O t EThYL ESTER I - N I C O T I N I C ACIO, ETHYL ESTER P I C O L I L I C ACID, ETHYL ESTER TETRAHVOROPtlTHALIMIUE P-AMIkOSALICVLIC ACIOIMETHYL ESTER OR TeOC A I NE PHENOXY ACE1 I C AC IO 1 P-AM I NO P - A C E T V L B E Y Z E h E S U L F O N A M I DE P- ACETYL BEN2 EN ESUL FONAM I DE
M-HYOROXY8EhZYLIOINETHIOUREA
OCTANOL OCTANOL OCTANOL 2 8 0 4 OCTANOL 2805 OILS 2 8 0 6 OCTANOL 28C7 OIETHVL E l l - E R 2808 CHCL3 2 8 0 9 CHCL3 2 8 10 BENZENE 2 8 1 1 TOLUENE 2 8 12 OCTANOL 2 8 1 3 CHCL3 28 1 4 CHCL3 BENZENE 2815 2 8 16 XYLENE 2 8 1 7 TOLUENE 2818 OCTANOL 28 1 9 CYCLOHEXANONE .: 2820 M E- I-BU 11 ETONE 2 8 2 1 CVCLOHEIANOL 2 8 2 2 OIETHYL E T k E R 2823 0 1 ETHYL ETHER 2 8 2 4 OIETHVL TI-ER 2 8 2 5 CHCL3 BENZENE 28 26 2827 I -BUTANOL 2 8 2 8 OCTANOL 2 8 2 9 OCTANOL 2 8 3 0 OCTANOL 2 8 3 1 CYCLOHEXANONE 2 8 3 2 ME-I-8UT.KETONE 2 8 3 3 CVCLOHEXANOL 2 8 3 4 OCTANOL 2 8 3 5 OCTANOL 2 8 3 6 OCTANOL 2 8 3 7 OIETHVL TI-ER 2 8 3 8 OIETHVL ETI-ER 2 8 3 9 CHCL3 2 8 4 0 CHCL3 284 1 CHCL3 2842 O I L S 2843 O I L S BENZENE 2844 BEN 7. EN E 2845 2 8 4 6 N-HEPTANE 2 8 4 7 N-HEPTANE 2 8 4 8 TOLUENE 2 8 4 9 CYCLOHEXANE 2 8 5 0 OCTPNOL 2 8 5 1 OLEYL ALCOHCL 2852 O I L S 2 8 5 3 CHCL3 2 8 5 4 TOLUENE 2 8 5 5 CYCLOHEXANE 2 8 56 OCTANOL 2 8 5 7 OCTANOL 2 8 5 8 OCTANOL 2 8 5 9 OCTANOL 2860 OCTANOL 2 8 6 1 OCTANOL 2 8 6 2 OCTANOL 2 8 6 3 HEXANE 28.54 OCTANOL 2865 OCTANOL 2 8 6 6 OCTPNOL 2867 OILS 2 8 6 8 N-HEPTANE 2869 O I L S 2 8 7 0 CYCLOHEXANCNE 2 8 7 1 OCTANOL 2872 C H C L ~ '2873 OCTANOL 2 8 7 4 OCTANOL 2 8 7 5 OCTANOL 2 8 7 6 OCTANOL ' 2 8 7 7 N-HEPTANE 2 8 7 8 OCT ANOL 2 8 7 9 N-HEPTANE 2 8 8 0 OCTANOL 2 8 8 1 N-HEPTANE 2 8 8 2 OCTANOL 2 8 8 3 OCTANOL 2 8 8 4 CHCL3 2 8 5 B EN2 EN 2 8 8 6 OCTANOL 2 8 t 7 CHCL3 8 ENZ NE 2888 2889 BENZENE 2 8 9 0 OCTANOL 2 8 9 1 OIETHYL ETkER 2 8 9 2 CHCL3 2 8 9 3 CHCL3 2 8 9 4 CHCL3 2895 BENZENE 2896 I-PENT. ACETATE 2 8 9 7 CCL4 2 8 5 8 OC TANOL 2 8 9 9 OCTANOL 2 9 0 0 OIETHVL E T k E R
2802 2803
1.96 1.96
0.85 0.85 -1.04
1.96 1.96
0.85
10
3 83 10 112 112 29 17 29 10 29 46 17 46 29 10 302 302
2.02
0.78 1.65 1.65 0.64 0.45 1.96 1.48 0.90 0.46
12
-0.26
0.54 1.26 2.18 1.54 1.61 0.35
0.85 0.27 A 2.02 = 0.80 A 2.12 A A 2.93 2.02 A 1.97 A ~. 1.96 = 2.56 A 2.04 A 1.85 A 1.51 A 2.05 A 1.26 =
= = = =
302
3 207 46 29 36 4 10 302 10 302 302 302 255 255 10 3 359 359 2 54 338 173 224 338 72 2 54 338 151 151 255 390 383 29 29 141 65 3 86 276 276 276 384 186
03 .0
12 0.28 -1.26 -1.95 0.72 0.76 0.85 0.65 1.91 1.05 1.32 3.09 2.95 1.16 0.48 0.50 0.89 0.88 0.48 0.00
0.42 0.38 0.37 0.07 -0.54 0.50 0.76 0.85
A A A A A
06 .5
= = =
44 44 44
0.30
-1.70 0.22 -1.70 -2.00 1.77 0.95 0.45 1.09 -0.89 0.81 0.61 1.81 2.95 0.62 0.94 0.87 0.86 1.16 1.24 -0.54 1.32 1.43 0.87 -0.01 0.28 0.25 0.71 0.20
3.09 2.95 1.16 1.28 1.29 1.41 1.39 1.06 1.19 1.47 1.59 3.13 0.45 1.63 0.40 1.98 2.11 2.95
=
=
=
8 8 N N N A A
A
=
A A A
44
0.62
0.94 0.87 0.86 1.16 1.24 1.32 1.43 0.87 1.18 1.41 0.20 0.24 1.61 -0.57 3.15 3.20 2.77 3.15 1.71 2.04 0.97 1.44 1.33 0.91 1.36 1.73 0.42 -0.47 -0.01
= = = = = = = =
A
= =
C8H803 C8H803 C8H803 C8H803 CBH803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8H803 C8HB03 C8H803 C8H803 C8H803 C8H803 C8H803 CBH803 C8H803 C8H803 C8H804 C8H804 CBH804 C8H804 C8H804 C8H804 C8H98R1 C8H9CL1 C8H9N101 C8H9N101 C8H9N101 C8H9N101 C8H9N101 C8H9Nl01 C8H9N101 CBH9N101 C8H9N101 CUH9N101 C8H9N101 CBH9N101 C8H9N101 C8H9N101 C8H9N101 CBH9N102 C8H9N102 CUH9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N102
391
349 349 349 381
C ~ H ~ N ~ O Z
C8H9N102 C8H9N102 C8H9N102 C8H9N102 C8H9N103 C8H9N103 C8H 9N103 C8H9N10351 C8H9N103S1 CBH9N301Sl C8H9N302 C8HlO C8HlO C8HlO C8HlO C8H10 C8HlO C8H10 C8HlOCLlNlO2 C8HlON105PlSl C8HlON105PlSl C8HlON105PlSl C8HlON106P1 C8HlON106Pl CBHlON106Pl C8HlON2Ol C8HlON2Ol C8HlON203S 1 C8H lON2 0 3 5 1 C8HlON203S 1 C8HlON2035 1 C8HlON203Sl C8HlON203Sl C8HlON203Sl CBHlON251 CBHlDN402 CBHlON402
370
249 302 217 217 276 2 26 255 301
14
07 07
=
N
-0.36
1.61 -0.57 3.15
= =
=
3.20
3.54 2.77 3.39 3.15 3.45 1.71 2.04 1.38 1.28 1.33 1.33 1.17 1.71 04 .2 -0.67 -0.66 -0.12 -0.35 -1.54 -0.06 -1.77 0.85 -0.07 -1.30
310
301 310 301 310 80 392 392 392 392 392 392 72
186
= = = *
8 8 = 8 8
8
113 343 113 393 343 343 343 186 218 3
15 2 15
63
04 .8
0.27
-0.14
2 2 2
A N N N A
-0.24 -1.72 0.85 -0.07
= = -0.30 8
1-ACETYL-2-PICOLINOYLHVDRAZINE I686261 BENZENE, ETHYL M- XVLEN E M-XVL EN E 0-XYLENE 0- XVLE h E P- X Y LENE P- XVL E k E 0- I l - E T t I Y L - 1-ETHYNYL-3-ChLOROALLYL ICARBAMATE 01 HETrlYLPARATHIOh 01 METHVLPARATHIOh OIMETHYLPARATrlION 01 HETHYLPARA-OXOh D I METHVLPARA-OXON OIMETtlVLPARA-OXON P - h I TROSOOIMtThYLAN I L I h E UREA, 1-METHYL 1-PHENY L SU LF AN I L A C E T A M 1OE S J LF AN I L ACETA4 I OE SULF A h I L A C E T A M I O E SULF A h I L ACE T A M I DE SULF A I L AC ET AM I OE N SU LF AN I L A C E T AM I DE SULFAN IL ACETAMI DE UREA, l - M E T H Y L - l - P H E N Y L - 2 - T H I O CAFFEINE CAFFEINE

LOGP OCT
NO. 2901 2902 2903 2904 2905 29C6 29Cl 2908 2909 2 9 10 2911 2912 2 9 13 29 14 2915 29 16 2911 2918 29 1 9 2920 2921 2922 2923 2924 2925 2926 2921 2928 2929 2930 2931 2932 2933 2934 2935 2936 2931 2938 2939 2940 2941 2942 2943 2944 2945 2946 2941 2948 2949 2950 2951 2952 2953 2954 2955 2956 2951 2958 2959 2960 2961 2962 2963 2964 2965 2966 29 6 1 2968 2969 2910 2911 2912 2913 2914 2915 2976 2911 2918 2919 29 80 2981 29 82 2983 2984 2985 2986 2917 29 88 29 89 2990 2991 2992 2993 2994 2955 2996 2991 2998 2999 3000
SOLVENT CHCL3 CHCL3 CHCL3 OILS
REF FOOT NOTE 394 359 322 311 2 249 4 395 234 368 206 325 42 42 42 12 14 12 68 21
LOGP SOLV
EMPIRICAL FORMULA
NAHE CAFFEINE CAFFEINE CAFFEINE CAFFEINE CAFFEINE CAFFEINE CAFFEINE CAFFEINE CAFFEINE CAFFIENE PURINE, 2 v 6 r 8 - T R I - M E T H V L S U L F O N V L 2 0 3-OIHETHVLPHENOL 2.3-01 METHYL PHENOL 2.4-OIHETHYLPHENOL 2 t 4- 0 I H ET HY L PHENOL 2 1 4-01 METHYLPHENOL 21 5-OIHETHYLPHENOL 21 5-Of METHVLPHENOL 21 5-OIHETHYLPHENOL ZI~-OIMETHYLPHENOL Zv6-OIHETHVLPHENOL 21 6-OIHETHYLPHENOL 21 6-OIMETHYLPHENOL 29 6-OIHETHVLPHENOL 31 4-01 M ETHVLPHENOL 3v4-OIHETHYLPHENOL 3.5-OIMETHVLPHENOL 3 r 5-01 METHYLPHENOL 39 5-OIHETHVLPHENOL 31 5-OIHEThYLPnENOL ETrrANOLt 2-PHENYL E T hANOL1 2-PnENVL H-ETHVLPHENUL H- ETHYL PHENOL H-THY LPHENOL 0-ETHYLPhEhOL 0-ETHVLPHENOL P-ET HVLPn ENJL P-ETHVLPHENOL P-ET hYLPHEYOL P-ET h Y LPiiENOL P- EThVLPk EYOL P- ET HY LPhENOL H-HETnVL8ENZYL ALCOHOL P-METHVLBENZYL ALCOHOL PHENETOLE 8EhZEhE~lt2-OIHYOROXV-4-ETHYL BENZENE, 1~2-OIHYOROXY~4-ETHVL BEhZENEt l r Z-OIHYOROXYI 4-EThVL BENLENEv 1 + 3 - O I M E T H O X Y 8ENZENE~1~4-OIHETHOXY BE NZ EN E t I t 4 - 0 I H E T HO X Y P-ETHOXYPHENOL P-METHOXY 8 ENZY L AL CO HOL PHEhOL~2-METhOXY-C-METHVL/P-HETHYLGUAIACOL/ PhENOLv 2-HETHOXV-4-METHVL/P-HEThVLGUAIACOL/ 2-PHENCXYETHANOL RESORCINOLS41 5-OIHETHYL RESORCINOL~~I~-O~HETHVL RESORCI~OL,2~5-OI~ETHVL 8EhZYL ALCOHOL e4-HYOROXVs 3-HETHOXY P~~ENOL~~I~-OIHETHOXV PHENOLI~I~-OIHET~OXV PHEhOL 9 2 1 6-OIHETHOXV P-ETHOXYPHENYLBORONIC ACID N1-ETnVLNICOTIhAHIOE CHLORIDE BEhLYLHETHYLAHINE BENZVLHETHYL AH I N 8EhZVLHETHYLAHINE N1N-OIHETHVLANIL I N NVN-DlHETHVLANIL I N Ne N-DIMETHYL AN I L I N 21 3-OIHETHYLANlL IN 2 1 4-01 HETHVLANIL INE 214-01METtiYLAhlL INE 2.4-OIHETHYLANILINE 21 5-OIHETHYLANILINE 2.5-DIMETHYLANILINE Z~bOIHETHYLANILINE 2.6-OIMETHVLANILINE 3 s 4-OIMETHYLANIL I h E 3*4-OIHETHYLANIL 1NE 3r 5-OIMETHVLANIL I N E ETHVLAMINEI 2-PHENVL ET HYLAH INEI 2-PHENYL ETHVLAHINEv 2-PHENYL N-ETHVLANIL INE PVRIOINEI 2-HETHYLv5-ETHVL PVRIOINE.2-METHYL~5-ETHVL PVRIOINEI~-PROPYL PVRIOINE~2~4~6-TRIHETHVL/COLLIOIN/ 3-OIHEIHYLAHINOPHENOL O-11-ETHVL-1-VINYL-2-PROPVNVLl CARBAMATE HEXAHVOROPHTHALIHIOE
BENZENE OCTANOL CYCLOHEXANE N-HEPTANE CYCLOHEXANE CYCLOHEXANE N-HEPTANE CYCLOHE X AN E CYCLOHEXANE N-kEPTANE OCTANOL OIETHYL ETkER CYCLOHEXANE CYCLOHEXANE N-HEPTANE CYCLOHEXANE N-HEPTANE OCTANOL CYCLOHEXANE CYCLOHEXANE N-kEPTANE OCTANOL HEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OILS OILS BENZENE PARAFFINS OC T ANOL OCTANOL CYCLOHEXANE OIETHYL ETkER 01-8UTVL ETHER 01-I-PR. ETbER CYCLOHEXANE OILS OILS OCTANOL OCTPNOL OILS PARAFFINS OCTANOL N-BUTYL ACETATE N-BUTYL ACETATE N-BUTYL ACETATE OIETHYL E T k E R OIETHYL ETkER OILS PARAFFINS BENZENE OCTANOL OIETHVL ETCER OIETHYL E T k E R XYLENE OCTANOL OCTANOL CYCLOHEXANE N-HEPTANE CYCLOHEXANE XYLENE N-HEPTANE CYCLOHEXANE N-HEPTANE CYCLOHEXANE N-PEPTANE XYLENE N-HEPTANE CYCLOHEXANE OCTANOL CHCL3 N-HEPTANE OCTANOL XYLENE TOLUENE OCTANOL TOLUENE OCTANOL OCTANOL OILS 01 ETHYL ETHER CHCL3 01 ETHYL E l l - E R CHCL3 OCTANOL OCTANOL
310 132
325
310
132 325 310 261 323 132 325 310 325 310 261 132 325 310 255 312
10
132 325 132 325 132 325 324 321 324 321 10 10 358
1.33 1.32 1.28 -0.40 -1.48 -1.13 0.08 -2.22 -0.68 -0.16 3.58 0.51 0.43 0.16 0.55 0.40 0.11 0.57 0.52 2.36 2.53 1.28 0.93 0.82 0.20 0.10 2.35 0.54 0.21 0.21 1.36 -0.39 2.40 0.43 0.36
0.91 0.86 0.87 0.18 -0.19
B
8
8 B
8 B
-0.50
-0.39 0.44 3.58
2.36 2.33
=
A
2.35
1.36 2.40
= =
0.83
0.68 0.44 0.31 1.79 1.62 1.44 0.04 1.60 1.58 2.11 1.65 0.88 1.39 2.32 2.15 2.21 1.81 1.10 1.26 0.11
12
45
2.81 2.66 2.18
A A A
1.60
1.58 1.51
=
=
A
332
332
332
358 113 224 261 10 321 321 56 331 331 331
2.16
3.14
3.20
1.81 1.10 2.33
1.16 1.26 1.62 1.82
A A
= =
A
1.16
1.21
1.64 1.94 -0.20 0.14 0.57
323
323 321 321 311 313 46 314 46 10 309 331
-0.06
0.76 1.69
A A A
-0.36 -0.01
-2.02 0.78
0.85
1.39
-2.02 1.54 1.61
2.03
2.31
2.62 2.41
2.31 = 2.62
8 B
310
331 46 310
1.00
1.23 1.18 1.85
337
310 331 310
1.10 1.22
1.12 1.35 1.21
46
310 331 255 396 396 312 13 73 9 188
1.05
0.95 1.18 1.41
1.70
31
31
1.32
-0.56 2.26 1.12 1.80
1.41 0.91
2.26
=
B
=
8
B
2.36
1.95 2.10
2.10
1.43 1.56 1.09
=
8
1.12
1.56 1.09 1.34 1.09 2.28 1.13 3.11 -2.14 0.74
10 80 381 113
113 113 113 221 391
= =
A A N A N
01 .6
11 .1 11 .1 1.16 2.69 -2.14 0.14
C8HlON402 CBHlON402 CBHION402 C8H 10N402 C8HlON402 C8HlON402 CBHlON402 C8HlON402 CBHlON402 C8HlON402 C8HlON40653 C8H1001 C8HlOOl C8H1001 C8HlOOl C8HlOOl C8H1001 C8HlOOl C8H1001 CBHlOOl C8H1001 C8H1001 C8H1001 C8H1001 C8H1001 C8HlOOl C8HlOOl CBHlOOl C8HlOOl C8HlOOl CBHlOOl C8HlOOl C8H1001 C8H1001 C8HlOOl C8H1001 C8HlOOl C8HlOOl C8HlOOl C8H1001 CBH1001 CBHlOOl C8H1001 C8HlOOl C8HlOOl C8HlOOl C8H1002 C8H1002 C8HlO02 C 8H 1 0 02 C8H1002 C8H1002 CBHlOO2 C8H1002 C8HlOO2 CBH1002 C8H1002 C8HlOO2 C8H1002 C8H1002 C8H1003 C8H1003 C8H1003 C8H1003 C8H118103 C8HllCLIN2OI C8H11N1 C8H1 I N 1 C8H11N1 C8H 11N 1 CBHllN1 C8HllN1 C8HllNl C8H11N1 C8HllN1 C 8 H l lN l C8HllNl C8HllNl C8HllNl C8H11N1 C8HllNl C8H11 N1 C8H11N1 C 8 H l 1N 1 C8HllNl C8H11N1 C8HllNl C8HllN1 C8HllNl C8HllNl C 8 H l 1N 1 C8HllNlOl C8HllNlOZ C8HllN102 C8H 11N102S 1 C8HllN102Sl C8HllNlOZSl C8HllN102S1 C8HllN306 C8HllN5
8ENZENESULFONAMIOE.N-ETHYL
BENZENESUL FONAM IO IN-ETHYL NVN-DIMETHYLBENZENESUL FONAMIOE N t N-01 METHYL BENZENE SUL FONAMI DE 6-AZAURIDINE INCS 3 2 0 1 4 ) l P K A = 6.63) ADENlNEe9-PROPYL
NO.
SOLVHlT
REF FOOT NOTE
LOGP SOLV
L06P OCT
3001 3002 3003
OCTANOL
OCTANOL CHCL3 OCTANOL OILS OCTANOL 01 ETHYL EThER CHCL3 CHCL 3 CHCL3 CHCL3 OILS OILS
341 341 322
60
0.49
60
44
3004
3005 3006
30C7
56
398 80 113 399 113 2 54 338 82 345 398 296 168 2 90 399 338 399 399 338 82 125 80 112 112 347 298 400 348 218 I34
01 .6 08 .8 08 .1
0.36
07 = .6
1.36
0.49
=
=
A
EMPIRICAL FORMULA C8Hl2N2 C8Hl2N2 t8Hl2NZOlSl C8Hl2N202Sl C8H12N2OZS1 C8H12N203 C8W12N203 CBHl2N203 C8HlZN203 C8H12N203 C8Hl2N203 C8Hl2N203 C8H12N203 C8Hl2N203 C8Hl2N203 C8Hl2NZ03 C8H12 N 2 0 3 C8Hl2N203 CBHl2N203 C8H12N203 C8HlZN203 C8H1 N 2 03 Z C8Hl2N203 C8H12N203 C8HlZO1 C8Hl202 C8H1202 C8H1202 CBH12SIl C8H13N102 CBH13N102 C8H13N102SI CBH14N40151 C8H14N401Sl CBH14N401Sl C8Hl402 C8H1403 C8H1404 C8H1404 C8H1404 C8H1404 C8H1404 C8H1404 C8H1404 C8Hl4Ob C8Hl406 C8H1406 C8H15K102 C8H15N101 C8H15N101 C8H15N101 C8Hl5N103 CBH15N103 CBH15N103 C8H15 N 1S 1 C8H15N307 CBH15NA102 C8H16N251 CBH1602 C8H17CL2N102 C8H17CL2N102 C8H17N1 CBHl7Nl C8H17 N 1 0IS 1 C8H18F103P1 C8H18F103Pl C8H1 8 N 202 C8H1801 CBH1801 C8H1803 C8H1803 C8H1804S2 C8H1804 S2 C 8 H 1 8 0 4 S2 C8H1805 COH1805 C8H19N1 C8H19Nl C8H19NI C8H19N1 C8H1902PIS2 C8H1902PIS2 C8H1902PISZ C8H1902PlS2 C8H1902S2 C8H1904Pl C8H1904 P 1 C8H1904PI C 8 H 1 9 0 4P I C8H1904Pl CBH1904Pl C8H1904P1 C8H1904P1 C8H1904P1 C8H1904P1 C8H1904P1 CBH1904P1 C8H1904P1 C8H1904Pl C8H1904Pl
NAME
N N-01METHYL-3-PYRI .
OYLMETHYLAMI NE
N-ETHYL-3-PYRIOVLMETHVLInlNE 2-METHIO-4-HVOROXVTRIMET~VLENEP~RI I 0 1 NE M
PHENETHYL SULFAMIOE 5~5-0IETHYL8AR~ITURIC ACIO/8AR8ITAL/VERONAL/ 5-01 ETHYLBARBITUR I C A C I O / B I R B I TAL/VERONAL/ 5.5-01 ETHVLBARBITURI C AC I O I B A R B I TAL/VERONAL/ 5 ~ 5 - O I E T H Y L B A R 8 I T U R I C ACIO/8ARBITAL/MRONAL/ 5 ~ S - O I E T H V L 8 A R B I T U R I C ACIO/8AR8ITAL/VERONAL/ 5 ~ S - O I E T H Y L B A R B I T U R I C ACIO/BAR8ITAL/VERONAL/ 5 9 5-01 ETHYLBARBITURI C AC I O l B A R B I TAL/VERONAL/ 5.5-01ETHYL8AR8ITURIC ACIO/BAR8ITAL/VERONAL/ 5s 5-OIETHYLBAR8ITURIC ACIO/BAR8ITAL/VERONAL/ 5 ~ 5 - 0 I E T H V L B A R 8 I T U R I CACIO/8AR8ITAL/VERONAL/ 5 ~ 5 - O I E T H V L 8 I R 8 1 T U R I C ACIO/8AR8ITAL/VERONAL/ 5 1 5-01 ETHYLBARBITURIC ACIO/BARBI TAL/VERONAL/ 5 ~ 5 - O I E T H V L B A R 8 I T U R I C ACIO/8ARBITAL/VERONAL/ 5 r 5 - D I E T H V L B A R 8 I T U R I C ACIO/BARBITAL/VERONAL/ 5 I 5-01 ETHYL BARBI TUR I C AC I O/BARB I T A L / VE RONAL/ 5r 5-OIETHYL8AR8ITURIC ACIO/BARBITAL/VERONAL/ 5.5-01ETHYL8AR8ITURIC AC IO/BARBI TALlVERONALl 5s5-OIETHYLBARBITURIC ACIO/8AR8ITAL/VEROkAL/ CYCLOHEXANOL 9 1-ETHYNYL C Y U O r i EXINE- I r 3-OIONE v 5 r 5-01 METHYL/OI MEDON/ CYCLOHEXANE-19 3-OIONE 9 5 1 5-OIMETHVL/OIMEOON/ SORBIC ACIOIETHYL ESTER SI LANE I DIMETHYL-PHENYL AR ECOL I N N-PROP IONVLCYCLOBUTANECARBOXAMIOE 31 5-THIOMORPHOL I N E O I O N E ~ 2 r 2 - O I E T H V L 3-THY LTHIO-4-AM INO-6- I-PR-1.2s4-TRI A2 I NE-5-ONE
59
06 .5
16 0.63 1 -0.14 -0.01 -0.15
08 .1 1.52 06 .5 0.67
0.49
3008
3009 30 10 3011 30 12
3013
0.54 04 .5
1.03
44
04 .5
-0.12 -0.67
05 .4
0.58 06 .8
A N N N N A
A
A A A A A
30 1 4 30 15 30 1 6
3017 3018 3019 3020 3021 3022 3023
3024
OILS
OILS OILS OILS BENZENE BENZENE I-PENT. ACETATE CCL4 N-HEPTANE OLEYL ALCOHOL 50XETHER+500MF OCTANOL DIETHYL ETHER CHCL3 OILS OCTANOL N-HEPTANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL CHCL3 OCTANOL DIETHYL EThER DIETHYL ETHER N-BUTANOL ETHYL ACETATE CYCLOHEXANONE 2-BUTANONE ME- I-8UT.KETONE OCTANOL DIETHYL ETkER 0 1 ETHYL ETHER I-OCTANOL OCTANOL 01 ETHYL ETFER I-BUTANOL CHCL3 CHCL3 CHCL3 OCTANOL OCTANOL I-OCTANOL PARAFFINS N-HEPTANE CHCL3 BENZENE I-BUTANOL XYLENE OCTANOL OILS CCL4 OIETHYL E l E R OCTANOL OILS DIETHYL 1 ER OILS OILS OILS OILS OIETHVL ETkER I-BUTANOL D I E T H Y L EThER I-BUTANOL OCTANOL I-BUTANOL CCL4 I-PENT. ACETATE CCL4 ME- I-BU1.K ETONE OCTANOL o I - e u T v L ETHER CHCL3 CHCL3 BENZENE BEN2ENE TOLUENE NITROBENZENE CCL4 01-BUTYL ETHER 01-BUTYL ETHER 01-I-PR. ETHER HEXANE ME-I-8UT.K ETONE S-PENTANOLS PARAFFINS
44 -0.58
12
-1.22 -0.57
-0.96
00 .8
0.69 0.32 0.62
1 -0.77 44 -1.85 1 0.58 1 -1.46 44 -2.15 01 .4
0.43 0.62 A
0.70
3025
3026 30 27
3028
-0.10 1.73 0.29 0.76 1.42

14
3.99 -1.15
0.55
1.13 0.37 1.30 2.48 3.99 -0.04 1.52 1.52 1.39 1.70 4.20
3029 30 30 3031 3032

3033 3034 30 3 5 3036 3037 3038 3039 3040 3041 3042 3043 3044 3045 3046 3047 3048 3049
-0.04
1.52 1.52
1.39
-4
A N
134
134 285 255 212 194 194 194 194 194 194
1.70 2.97 05 .5
0.67
0.55
0.70 0.54 08 .0 0.70
0.72
=
= =
A A A
3-MET~I0-4-AMINO-6-I-8U-1~2~4-TRIAZINE-S-ONE
~-METHIO-~-AMINO-~-T-~U-~~~ICTRIAZINE-~-O~E b-METHVL-2~4-HEPTANEOIONE/I-VALERVLACETOhE/ HEPTANOIC ACID, +KETO METHYL E S T E R SUBERIC A C I D SJBERIC A C I D SUBERIC A C I D SUBERIC A C I D SUBERIC ACIO SUBERIC A C I D SUBERIC ACIO TARTARIC A C I O ~ O I E T H V LESTER TARTAR I C AC I O t 01 ETHYL E S T E R TARTARIC ACIOIOIETHYL ESTER POTASSIUM OCTANOATE 2-AZACYCLONONAhONE TROP I N E TROPINE 0- ISOLEUCINE. ACETYL 0-LEUC INEI ACETYL NORL EUC I N 9 ACETYL 2- AZACYCLOhONANTHl ONE STREPTOZOTOCIN (NCS 8 5 9 9 8 1 SOOIUM OCTANOATE N- AMYL ETIIVL ENE TH IO UR EA OCTANOIC ACIO
04 .7
0.92 0.70 0.85
56 3
40 1 353 260 3 4 67 67 67 260 221
06 .8 0.68 -0.29 -0.19

-0.35 -1.38 0.67 -1.28 0.49
0.74 -0.29
-0.05
-0.19
A A
0.67
30 50
3051 3052
-0.28
0.21
3053
3054 3055 3056 3057 3058 3059 3060 3 0 6I 3062 30t 3 3064 3065
-0.77 -0.84 -0.70

1.44 -1.45 -1.38 -0.57 0.63 -0.92 -1.77 1.99 1.95 1.81 1.79 2.01 1.44 -1.45
= =
353
241 139 402 402 4 31 46
46
01-I-PROPYLAHMONIUM-OICHLOROACETATE
01-I-PROPYLAMMONIUM-OICHLOROACETATE 2-PROPYLP I P ER I 0 1NElCONI I N E /
46
2 18
271
2.29 2.61 1.81 1.92
8 8
2-PROPVLPIPERIOINE/CONIINE/
PROPIONAMIOEI 2-BUTYLTHIO-2-METHYL
3066
3067 3068 3069 3070 3071 3072 3073 3074 3075 3076 3077 3078 3079 3080 3081 30 82 3083 3084 30E5 3086 3087 3088 308 9
3090
271
378
44
1.77
0.06
01 BUTYLFLUOROPHOSPHATE 01 8UTYLFLUOROPHOSPHATE
h-METHVLCARBAHIC ACIOIOIETHYLAMINOETHYL OC TAN0 L OCTANOL 01 ETHYLENE GLYCOLvMONOBUTVL ETHER DIETHYLENE GLYCOL.MONOBUTYL ETHER 2.2-815( ETHYLSULFONYL IBUTANE/TR IONAL/ 2.2-BIS (ETHYLSULFONYL I BUTANE/TR IONAL/ 2.2-8IS( ETHYLSULFONYL )BUTANE/TRIONAL/ T E T R A E T HYL ENE GLYCOL TETRAETHYLEhE GLYCOL 01-I-BUTYL AM I N E 01-I-8UTYLAMINE OIBUTYLA4IkE OCTVLAMINE PHOSPHOROOITHIOTIC ACIO.01-I-BUTYL PHOSPHOROOITHIOTIC ACIO.01-N-BUTYL PriOSPHOROOITHIOTIC ACIDtOI-N-BJTVL PHOSPHOROOITHIOTIC ACIOvOI-N-BUTYL ETHYLPHOSPHONATE.0-ET-S-I 2-ET-THIOETHVL) 01-I-BUTYL PHOSPHATE DIBUTYL PHOSPHATE DIBUTYL PHOSPHATE DIBUTYL PHOSPHATE DIBUTYL PHOSPHATE OIBUTYL PHOSPHATE 0 1 BUTYL PHOSPHATE DIBUTYL PHOSPHATE DIBUTYL PHOSPHATE O I W T Y L PHOSPHATE DIBUTYL PHOSPHATE OIBUTYL PHOSPHATE OIBUTYL PHOSPHATE 01 BUTYL PHOSPHATE O I W T Y L PHOSPHATE ESTER
5
201 2 2 173 168 214 3 4 3
-1.00 3.15 1.77 0.04 -0.92 0.72

0.66 0.65 -2.62 -0.62 2.52 2.38 2.68 2.35 2.63
4
218 4
135
135
135
135
56
236 50
17
403
50 404 404
2.23 2.52 2.54 2.03 1.04 0.24 0.34 -0.42

-0.42
3.15 2.80 0.15 0.40 1.04 0.98 0.97 -2.18 -1.38 3.04 2.84 2.68 2.90 2.33 2.13 2.26 2.27 2.03
1.44 1.53
=
A A A 8 8 8 A
=
8
=
A A A A A
10 .0
0.94
3091 3092 3093 3094 3095 3096 3097 3098 3099 3100
50
50 50 236 50 50 50 2 74
~~
-0.70 -0.14
17
-1.44 -0.14 1.18 0.52 -2.34 1.36 2.21 -1.96
0.63
1.15
1.19
50

LOGP OCT EMPIRICAL FORMULA C8H1904Pl C8H1904 P 1 C8H1904Pl C8H20CLlNl C8H2OIlNl CBHZOI 1 N 1 C8H21N105 C9H4C L3N 1025 1 C9H4CL3N102S 1 C9H4F3N3 C9H5CLl I l N l O l C9H5CLlN4 C9H5CL2F3NZ C9HbCLlF3N2 C9HbCLlNl C9HbCLlN1 C9HbCLlN101 C9HbCLIN103 C9HbNlS1 C9H6N202 C9H6N202 C9H6N202 C9H6N202 C9H6N4 C9Hb02 C9H602 C9Hb02 C9H602 C9H602 C9H602 C9H606 C9H606 C9H7CLlN204 C9H7CL105 C9H7CL2N102 C9H7CL2N102 C9H7CL2 N202 C9H7F3N2 C9H7F302 C9H7F303 C9H7F303 C9H7F303 C9H7F303Sl C 9H7 F 3 0 4 C9H7F305S1 C9H7Nl C9H7N1 C9H7N1 C9H7Nl C9H7N1 C9H7N1 C9H7NL C9H7N101 C9H7N101 C9H7N10 1 C9H7N 10 1 C9H7N 101 C9H7N101 C9H7N101 C9H7Nl01 C9H7N101 C9H7N101 C9H 7N10 1 C9H7N101 C9H7N102 C9H7N102 C9H7N103 C9H7N103 C9H7N104 C9H7NlSI C9H7N1 S 1 C9H7NlSl C9H7NlS 1 C9H8 C9H88RlN102 C9H88RlN102 C9H8CLlN102 C9HBCLlN102 C9H8CLlN102 C9H8CL3N102Sl C9HBCL3N 1 0 2 S l C9H8CL3N10351 C9HBC L 3 N1 0 3 s 1 C9HBFlN102 C9H8FlNlO2 C9HBFlN102 C9H8F3N102 C9H81203 C9H8I204 C9H8N2 C9H8NZ C9H8N2 C9H8N2 .~ C9H8N2 C9H8N202 C9H8N202 C9H8N202 C9H8N202Sl C9HBN204 C9H8N204
NO.
SOLVENT PARAFFINS DIETHYL ETHER ME- I-BU1.K ETONE CHCL3 0 CTAN0 L NITROBENZENE 1-8UTANOL OCTANOL OLEYL ALCOHOL CYCLOHEXANE CHCL3 HEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL CHCL3 OCTANOL OCTANE OCTANOL OCTANOL OCTANOL OCTANOL HEXANE OCTANOL CYCLOHEXANE OILS OCTANOL OCTANOL CYCLOHEXANE DIETHYL ETbER I-BUTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANONE CYCLOHEXANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE OCTPNOL OC T A NOL CYCLOHEXANE XYLENE OCTANOL CYCLOH E X AN E OCTANOL OCTANOL OCTANOL CHCL3 CHCL3 N-BUTANOL TOLUENE PRIM. PENTPNOLS I-PENT. ACETATE CCL4 ME- I-BU T . E TONE K 0-OICL. BENZENE OCTANOL CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE CHCL3 BENZENE CCL4 OCTANE OC TANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOHOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OILS OILS OCTANOL OCTANOL HEXAOECANE DECANE CYCLOHEXANE OCTANOL OCTANOL JCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE
REF FOOT NOTE 404 236 17 17 46 46 46
L06P SOLV
NAME DIBUTYL PHOSPHATE OCTYL PHOSPHATE OCTYL PHOSPHATE TETRAETHYLAMMONIUM CHLORIOE TETRAETHYLAMMONIUM IOOIOE TETRAETHYLANHONIUH IOOIOE TETRAETHANOLAMMONI M HYOROXI DE U N-lTRICHLOROHETHYLTHIO~PHTHALIHIOE/FOLPET/PHALTAN/ N-TRICLMETHIOPHTHALIMIOE/PHALTAN/ t-TRIFLUOROMETHYL-5-CYANO-8ENZIMIDAZOLE 8 - W I N O L I N O L r 5-CHLORO-7-1000 CARBONYL CYAN1DE.H-CHLORO-PHENYLHYORAZONE 2-TRIFLUOROHE-4r6-OICL-5-ME-8ENZIMIOAZOLE 2-TRIFLUOROHE-6-CL-5-ME-8ENZIMIOAZOLE 6-CHLOROQUINOL INE 8- CHLOROPUINOL I N E 8- CUI NOL I NOL 9 5-CMORO PHENOXYACET I C A t I O , 3-CYANO-4-CHLORO W INOLINE.~-~ROMOI 8-MERCAPTO 5-NITROPUINOLINE 6-NITROPUINOL INE 7-NITROPUINOLINE 8-NITROPUINOLINE CARBONYL CYANI0E.PHENVLHYDRAZONE COUMARIN COUMARIN COUMARIN 1~3-INDANOIONE 1.3-INOANEOIONE l r 3-INCANEOIONE BENZENE, 1 ~ 3 ~ 5 - T R I C A R B O X V L I C ACID B E N Z E N E I ~ ~ ~ ~ ~ - T R I C A R B O X YACID LIC S T Y REN E t 2-CHLORO I 5-N I T R O 9 8-N ITRO 8-ME THY L PHENOXYACETIC ACIOt3-CARBOXY-4-CHLORO STYRENE~3r4-OICHLORO18-NITROIB-METHYL STYRENE, 2 r b-OICHLORO, 8-N 1TRO.B-METHYL STVRENE~2r4-OICHLORO~8-NITRO1B-nETHYL 2-TR1FLUOROHE-5-HETHYLBENZIMIOAZOLE H-TRIFLUOROMETHYLPHENYLACETIC A c t 0 H-TRIFLUOROMETHYLPHENOXYACETIC ACID H-TRIFLUOROMETHYLPHENOXYACETIC ACIO H-TRIFLUOROHETHYLPHENOXYACET I C A C I 0 H - T R I F L U O R O M E T H Y L T H I O P H E N O X Y A C E T I C ACID M - T R I F L U O R O M E T H O X Y P H E N O X Y A C E T I C ACID H-TRIFLUOROMETHYLSULFONYLPHENOXYACETIC ACID CINNAMONITRILE QUINOLINE QUINOLINE QUINOLINE PUINOLINE I- W INOLINE I-QUINOLINE 2-CUINOLINOL 8-PU INOL INOL ~-~UINOLINOL 8-PU INOL INOL 8-WINOLINOL 8- W INOL INOL 8-W INOL INOL 8- PU I NOL I NOL 8-PUINOLINOL 8-PUINOLINOL 8-P~INCLINOL 8- au I NOL N L IO H-CVANOPHENYLPHENYLACETIC ACID PHTHhLIMI0E.N-METHYL PHENOXYACETIC ACID.4-CYANO PHENOXYACETIC ACIOv3-CYANO STYRENEI~~~-OIOXYMETHYLENEIB-NITRO 8-PU INOL I NETHl OL 8-WINOLINETHIOL 8-QU INOLINETHIOL 8-PU INOL INETHIOL INDENE STYRENE, 2-BROHO1 8-N I T R O I 8-METHYL S T YRENEt 3-8ROMO. 8-NITRO, B-METHYL STYRENE~3-CHLORO.B-NITRO.8-METHYL STYRENE~~-CHLOROIB-NITRO~B-METHYL STYRENE-2-CHLORO.8-NITROIB-HETHYL CAPTAN N-1TRICLHETHIO)-TETRAHYDROPHTHALIMIOE/CAPTAN/ N-TRICHLMETHIO-3.6-ENOOXOHEXAHYOROPHTHALIMIDE
N-TRICLMETHIO-4.5-EPOXYHEXAHYOROPHTHALIMIOE
3101 3102 3103

3104 3105
236
405 297 92 184
3106
31'27
-1.96 1.62 1.45 -2.52 -2.82 -1.65
1.28
-2.82 28 .5
3.70
= =
-1.14
19 14 19 19 14 2.85 3.13 -1.15 1.58 0.58 1.18 -0.07 2.73 2.33 1.12
3108
3109 3 1 10
235
406 379 407 29 9 379 379 216 268 407 302 408 216 216
3111 3 1 12 3113
3114 3115
3116
3 11 7 3118 3119 3120 3121 3122 3123 3124 3125
2.73 2.33
= = =
1.56
2.63
1.56
1.86 1.82
1.40 1.39
18 .6
1.84
= 1.84 = = =
216
216 299 218 304
1.82
1.40
0.21
1.39 0.48 1.21
3126
3127
3128
3129 3130
173 218
409 304
06 .1 03 .6
-0.12 1.04 1.48 2.46 1.07
1.42 8 06 = .1 0.36 =
3131 3132
3133 3134 3135 3136 3137 3138 3139 3140 3141 3142 3143 3144 3145 3146 3147 3 148 3149 3150 3151 3152 3153 3154
3
4 141 302 141 141 141 379
10 .3
1.57 1.07
33 .6
4.40
3.61
19
-0.48 2.62 2.62
10 10
302 302 10
23 .6
3.42 2.72 2.86 2.48 2.19 1.53 2.03 2.06
2.36 = 28 .6
2.48 2.19
=
=
10 10
141 255 309 2 80 46 186 280 65 410 349 411 412 410 410 410 410 412 410 410
= =
8
2.03 2.06
1.81 2.08
1.26
1.14 2.08
1.11 1.26
1.96 2.02 2.60 2.64 1.67 2.21 1.79 2.24 2.06
12 .6
1.96 2.02 1.90 2.06
3155
3156 3157 3158 3159 3160 316 1 31t2 31.53 31t4 3165 3166 3167
= =
8 8
8
B
1.81 2.26
1.96 2.14 1.89 1.90 1.18 0.93 0.95 1.94 2.08 1.76 2.92
2.13
2.48 1.18 0.67 0.93 0.95 1.41 2.51 2.20 1.91
10
304
3168
3169 3170 3171 3172 3173 3174 3175 3176 3177 3118 3179 3180 3181 3182 3183 3184 3185 3186 3187
10 10
141
413
=
B
3188
3189 3 190 3191 3192 3193 3194 3195 3196 3197 3198 3199 3200
413 413 413 28 3 141 141 141 141 141 235 406 406 406 141 141 141 384 382
8 8
=
1.02
2.92 3.01 3.05 2.63 2.97 3.31 2.35
2.35
2.72
2.15
1.65
0.85
2.22
1.42
3 82
216 216 314 314 280 3 84 3 84 3 84 216 141 141
24 24
2.47 2.57 2.67 2.37 3.99
2.30 1-16
1.79 -1.78 -1.78 1.28 1.11 0.97 0.95
2.37 4.82 3.28 1.16 1.79
=
A A
0.36
1.52 1.59
1.11 = 0.97 = 0.95 = 0.36 =
STYRENE~~-FLUOROIB-NITROIB-HETHYL STYRENE~3-FLUORO~B-NITRO~B-METHYL STYRENE.2-FLUORO~B-NITRO1B-HETHYL N-METHYL-3-TRIFLUOROMETHYLPHENVLCAR8AMATE BENZOIC A C I O ~ 4 - O H ~ 3 ~ 5 - O I - I O O O I f T H Y LESTER BENZOIC AC 10131 5-0 I - IO DO t 4-OH1 6-HYOROX Y E TH Y L E S T E R 5-AHINOPUINOLINE 8-AMINOPUINOLINE 0-PHENYLENE0 I AMINE 0-PnENVLENEOIAMIhE W IhOL INEv 3-AM I N 0 h-MElHVL-2-CYAhOPHENYLCAR8AMATE N-METHYL-3-CYANOPHENYLCARBAMATE N-METHYL-4-CYANOPHENYLCARBAMATE 8-SULFONAMIDOPUINOLINE STYRENE.2-NITROsB-NITROIB-HETHYL STYRENEs4-NITROq 8-NITROvB-METHYL
NO. 3201 3202 3203 3204 3205 3206 32C7
SOLVENT
REF FOOT NOTE 141 238 304 218 149 29 46 29 149 268 186 218 46 29 2 54 46 29 254 10 414 10 10 302 255
LOGP SOLV 1.62 1.88 0.96 2.13 1.20 1.97 0.15 1-60
LOGP OCT 1.88 2.13 2.31 3.01 1.97 2.98
EMPIRICAL FORMULA C9H8N204 C9H801 C9H801 = C9H802 A C9H802 A C9H802 A C9H802 A C9H802 C9H802 = C9H802Sl = C9H804 = C9H804 A C9H804 C9H804 A C9H804 A A C9H804 A C9H804 CPH804 = C9H804 A C9H804 = C9H804 C9H805 C9H805 = C9H9N1 = C9H9Nl = C9H9N1 = C9H9N1 C9H9N101 = C9H9N 1 0 2 C9H9N102 = C9H9N102 C9H9N102 C9H9NlO2 = C9H9Nt03 A C9H9N103 C9H9N 103 A = C9H9N103 C9H9N103 C9H9N103 C9H9N 103 = C9H9N104 C9H9N104 = C9H9N3 02 SZ = C9H9N30252 8 C9H9N302S2 8 C9H9N302S2 N C9H9N302S2 N C9H9N302S2 N C9H9N302S2 C9H9N302SZ C9H9N302SZ N C9H9N302SZ A C9H9N3 02 52 C9H9N302S2 A C9H9N302SZ C9H9N302S2 = C9H10 = C9H10 C9HlOCLlN102 = C9HlOCLlN102 C9H lOCL 1N103 C9HlOCL3N102Sl A C9H10 I I N 1 0 4 5 1 A C9H 1 0 I 1N104S1 C9H1011N104Sl A C9H1011N105S1 A C9H1011N105S1 A C9H10 I 1N105S 1 C9H1011N105S1 = C9HlON2 = C9HlON204 = C9HlON402S2 N C9HlON402S2 N C9HlON402SZ A C9HlON402S2 C9HlON40252 A C9HlON402S2 C9HlON40252 = C9H1001 = C9H1001 C9H1001 C9H1001 = C9H1001 = C9H1002 A C9H 100 2 C9H1002 = C9H1002 = C9H1002 = C9H1002 A C9H1002 A C9H1002 = C9H1002 A C9H1002 A C9H1002 A C9H1002 A C9H 1002 A C9H1003 C9H1003 A C9H1003 C9H1003
NAME STYRENEI~-NITROI~-NITROIB-HETHYL AC RYLOPHENONE 1-INOANONE C I NNAM I C AC I D/TRAN S / C I N NAM I C AC 1 0 / TRAN S CINNAMIC ACIO/TRANS/ CINNAMIC ACIO/TRANS/ CINNAMIC ACIO/TRANS/ CINNAMIC ACIO/TRANS/ 51 7-OIMETHYL-2-OXO-1~3-8ENZOXATHIOL ACETYLSAL ICYL I C AClD/ASP I R I N / ACETYLSALICYLIC ACIO/ASPIR I N / ACETYLSALICYLIC AC IO/ ASP I R I N / ACETYLSALICYLIC A C I O / A S P I R I N / ACETYLSALICYLIC A C I O / A S P I R I N / ACETYLSALICYLIC A C I O / A S P I R I N / A ETYLSALICYL I C AC IO/ASP I R I N / C ACETYLSALICYLIC A C I O / A S P I R I N / M-CARBOXYPHENYLACETIC ACID HOMOPHTHALIC ACID ISOPHTHALIC ACIDIMETHYL ESTER PHENOXYACETIC ACIOIM-CARBOXY PHENOXYACETIC ACIDIM-CARBOXY BENZYLACETONITRILE BENZYL ACETON I T R I L E INOOLEt +METHYL INOOLE. 5-METHYL CINNAHAMIDE ST YRENEI 8-METHYL-8-NI TRO STYRENE, 8-METHYL-8-NITRO STYRENEI~-METHYL-E-NITRO STYRENE, 2-METHYLs8-NITRO STYREN 9 4-M ETHYL, 8-NITRO 0 - A M INOBENZO I C A C I DIN- A ET Y L C GLYC1NE.N-BENZOYL/HIPPURIC ACID/ GL YC I N E. N-BENZOY L I H I P PUR I C AC IO I STYRENEI 3-HETHOXY-8-N I TRO STYRENEI~-METHOXY,B-NITRO STYRENEI~-METHOXYIB-NITRO STYRENE, 2-METHOXY, 8-NITRO STYRENE~4-HYOROXY-3-METHOXY-8-NITRO ST YREN E, 4-HY O R O X Y I 3-METHOXY v 8-N I TRO SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIlZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE SULFATHIAZOLE ALLYLBENZENE 1-PROPENEv 1-PHENYL N- ME T HY L CAR 8 AM AT E t 3- M ETHYL v 4-C H LOROPHE NYL N-METHYL-3-METHYL-4-CHLOROPHENYLCAR8AMATE P-AMINOSAL ICYL I C ACfOt 2-CHLOROETHYL ESTER
CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CHCL3 CHCL3 XYLENE 3208 TOLUENE 3 2 0 9 ME- I-8UT.K ETONE 3 2 1 0 OCTANOL 3 2 1 1 OCTANOL 3 2 1 2 OCTANOL 3 2 1 3 DIETHYL TI-ER 3 2 1 4 CHCL3 3 2 1 5 CHCL3 3 2 1 6 XYLENE 3 2 1 7 TOLUENE 3 2 1 8 N-HEPTANE 3 2 1 9 OCTANOL 3220 DIETHYL E T P E R 3 2 2 1 OCTANOL 3 2 2 2 OCTANOL 3223 CYCLOHEXANOL 3 2 2 4 OCTANOL 3 2 2 5 OCTANOL 3 2 2 6 OCTANOL 3 2 2 7 OCTANOL 3 2 2 8 CYCLOHEXANE 3 2 2 9 OCTANOL 3230 CYCLOHEXANE 3 2 3 1 OCTANOL 3 2 3 2 CYCLOHEXANE 3 2 3 3 CYCLOHEXANE 3 2 3 4 OCTANOL 3235 DIETHYL ETHER 3 2 3 6 DIETHYL TI-ER 3 2 3 7 OCTANOL 3 2 3 8 CYCLOHEXANE 3 2 3 9 CYCLOHEXANE 3 2 4 0 CYCLOHEXANE 3 2 4 1 OCTANOL 3 2 4 2 CYCLOHEXANE 3 2 4 3 OCTANOL 3 2 4 4 OCTANOL 3245 DIETHYL Ti-ER 3246 DIETHYL TI-ER 3 2 4 7 CHCL3 3 2 4 8 CHCL3 3 2 4 9 CHCL3 3250 CHCL3 3251 CHCL3 3252. CHCL3 3253 BENZENE 3254 I-PENT. ACETATE 3255 CCL4 3 2 5 6 N-i-EPTANE 3 2 5 7 OCTANOL 3 2 5 8 OCTANOL 3 2 5 9 HEXANE 3 2 6 0 OCTANOL 3 2 6 1 N-CEPTANE 3 2 6 2 OLEYL ALCOHOL 3 2 6 3 CHCL3 3 2 6 4 CCL4 3 2 0 5 CLCH2CH2CL 3 2 6 6 DIETHYL ETHER 3 2 6 7 CHCL3 3268 ETHYL ACETATE 3 2 6 9 CLCH2CH2CL 3 2 7 0 OCTANOL 3 2 7 1 OCTANOL 3 2 7 2 OCTANOL 3 2 7 3 CHCL3 3 2 7 4 CHCL3 3 2 7 5 BENZENE 3276 I-PENT. ACETATE 3 2 7 7 CCL4 3 2 7 8 N-kEPTANE 3 2 7 9 OCTANOL 3 2 8 0 OCTANOL 3 2 8 1 CYCLOHEXANE 3 2 8 2 CYCLOHEXANE 3 2 8 3 OCTANOL 3 2 8 4 OCTANOL 3 2 8 5 CHCL3 3 2 8 6 N-HEPTANE 3 2 8 7 OCTANOL 3 2 8 8 OCTPNOL 3 2 8 9 OCTANOL 3290 OILS 3 2 9 1 OILS 3 2 9 2 OCTANOL 3 2 9 3 CHCL3 3294 OILS 3295 OILS 3 2 9 6 XYLENE 3 2 9 7 OIETHYL ETkER 3 2 9 8 CYCLOHEXANE 3 2 9 9 BENZENE 3300 CLCHZCHZCL
~~
12 12
2.33 3.25
1.23 1.19
20 .8
3.25 1.23 1.19 1.13 1.45 1.46 1.16 1.12 1.14 0.46 1.83 1.11 1.72 1.66 2.60 2.68 2.52
1. I5
0.26
0.30
-0.57 -0.49
-1.52
1.14 0.40 1.83
1.11
1.75 1.72 1.66 2.60 2.68 -2.21 2.52 2.69 2.28 2.40 2.42 1.88 -0.41 -0.22 2.30 1.73 1.89 2.15 1.88 0.04 0.35 0.05 -0.72 -0.99 -0.82 -0.75 -0.87 -0.80 -0.73 -0.74 -0.96 -0.28 -1.57 -4.60
302
309 309 304 141 141 141 141 141 56 3 46 141 141 141 141 141 141 393 56 342 113 343 113 326 344 393 415 343 343 343 415 235 9 391 3 84 416 406 306 306 306 306 306 306 306 206
26
2.28
1.88 -0.25 -0.07 2.30
1.88
0.35 0.05
63
15 2 15
44 63 44
0.21 -0.03
-0.16 -0.09 -0.21 -0.14 -0.68 -0.08 0.43 -0.47 0.54
2
2 2 44
3.23 33 .5
14 12 12 0.58 2.57 0.49 2.40 0.48 -1.40 0.74 0.62 -1.30 1.34 -0.82 2.35 0.26 0.54
3.23 3.35
2.57 2.97 1.60 0.65 0.70 0.04 1.49 2.35 0.26 0.54
N-TRICLMETHIOHEXAHYOROPHTHALIMIDE
N-(P-IOOOBENZENESULFONYL )ALANINE N- (P-IOOOBENZENESULFONYL JALANINE N-(P-IOOOBENZENESULFONYL )ALANINE N- IP-IOOOBENZENESULFONYL 1 SERINE N- (P-IOOOBENZENESULFONYL JSER INE N-lP-IOOOBENZENESULFONYL)SERINE N- (P-IOOOBENZ ENESULFONVL )SERINE BEN2 I M I OAZOLEI 51 6-OIMETHYL PHENOXYACET I C AC I D , 3-UREIOO SU LFAMETHI ZOLE SULFAMETHIZOLE SULFAMETHIZOLE SULFAMETHI ZOLE SULFAMETHIZOLE SULFAMETHI ZOL E SULFAMETHI ZOLE ALLYLPHENYL ETHER CINNAMYL ALCOHOL 4-INOANOL 5- INOANOL 2-PROPANONEvl-PHENYL ACETIC ACIOIBENZYL ESTER P-HVOROXYPROPIOPHENONE P-WOROXYPROPIOPHENONE M-METHYLPHENYLACETIC Ac1o P-METHYLPnEhYL ACETIC AC IO PHENYLACETIC ACIOIMETHVL ESTER A-PHENYLPROP I O N I C ACID A-PHENYLPROPIONIC ACID 8- PHENYL PROP ION I C AC IO 8-PHENVLPROPIONIC ACID 8- PHENVLPROP I O N I C AC IO 8- PHENYL PROP I O N I C ACIO E-PHENYLPROPIONI C ACID BENLAL DEHVOEI 3-ETHOXYHVOROXYIETHYL VAN1 L L I N/ BENLALCEHVOE. 3-ETHOXY-~HVOROXY/ETHVL V A N I L L I N / ~ENZMDEHYOEI~-ETHOXY-~HYOROXV/ETHVL ANILLIN/ V ~ENZALDEHVOEI~-ETHOXV-~-HYOROXV/ETHVL VANILLIN/
10
56 343 415 343 343 343 415 218 56 2 44
-0.05
-0.43 -1.77 0.34 -1.82
0.53 0.21
-0.36 0.18
2
2
2
44
0.33
2.94 1.95 1.44 1.96
-3.83
2.94 1.95 0.61 0.48 1.44 1.96 0.71 -0.92 1.95 1.86 1.83 0.51
325
325 255
255
2 54 2 54
1.83
1.95 1.86 1.83
10
10 255 362 385 255 46 361 417 46 248 248 24 8 248
16 .8
1.91 1.84 2.22 1.91 1.92 2.29 1.29
2.81
0.75
1.84
1.10
0.72 0.82 0.46 1.34
0.03
1.43 1.86

NO. 3301 3302 3303 3304 3305 3306 SOLVENl OCTANOL OCTANOL OCTANOL REF FOOT NOTE 56 10 10 383 10 10 268 LOGP SOLV 2.47 1.50 1-42 0.45 1.78 2.10 1.86 2.46 2.05 1.90 0.86 0.93 1.23 1.38 2.40 1.80 0.06 1.07 0.01 0.88 3.72 3.55 1.41 2.95 -1.38 3.90 0.18 0.91 LOGP OCT 2.47 1.50 1.42 1.63 1.78 2.10 1.86 2.46 2.05 1.90 1.98 0.93 1.23 1.38 EMPIRICAL FORMULA NAME
= =
A
OILS
OCTANOL OCTANOL OCTANOL CYCLOHEXANONE CVCLOHEXANOL OCT ANOL OILS OCTANOL OCTANOL OCTANOL CYCLOHEXANONE CYCLOHEXANOL OCTANOL 01 ETHYL ETCER OCTANOL CYCLOHEXANOL OCTANOL OCTANOL HEXANE OCTANOL OCTANOL OCTANOL BENZENE OCTANDL OILS OILS OCTANOL I-PENT. ACETATE OLEYL ALCOHOL OCTANOL OILS OILS OCTANOL OCTANOL HEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL N-HEPTANE OCTANOL OCTANOL OCTANOL OCTANOL N-HEPTANE OCTPNOL OCTANOL OCTANOL OCTANOL BENZENE BENZENE CHCL3 N-HEPTANE N-BUTANOL N-BUTANOL OCTANOL OCTANOL OCTANOL N-HEPTANE N-HEPTANE N-CEPTANE N-HEPTANE CHCL3 I-PENT. ACETATE CCL4 OCTANOL CHCL 3 BENZENE I-PENT. ACETATE CCL4 N-BUTANOL N-EUTANOL CCL4 CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL HEXANE CYCLOHEXANE CYCLOdEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE DIETHYL ETHER 01-BUTYL ETHER 01-I-PR. ETHER
33C7
3308 3309 33 10 3311 33 12 33 1 3 33 14 3 3 15 3316 3317 3318 3319 3320 3321 3322 3323 3324 3325 3326 3321 3328 3329 3330 3331 3332 3333 3334 3335 33 36 3337 3338 3339 3340 3341 3342 3343 3344 3345 3346 3347 3348 3349 3350 3351 3352 3353 3354 3355 3356 3357 3358 3359 3360 3361 3362 3363 3364 3365 3366 3367 3368 3369 3310 3371 3372 3373 3374 3375 3376 3377 3378 3379 3380 3381 3382 3383 3384 3385 3386 3387 3388 3389 3390 3391 3392 3393 3394 3395 3396 3397 3398 3399 3400
19
302
302
10
173 10
= = = = = = = =
10
10 302 302 10 323 10
0.06 = le05 A 0.01 = 3.72 3.55 2.95 -1.38 3.90 1.55 0.91
302
2 55 255 391 255 226 56 72 255 173 224 349 418 390 186 173 224 276 27 6 391 3 84 384 384 56 384 370 384 384 384 56 370 56 298 255 218 311 311 396 396 295 295 341 186 218 419 419 419 419 399 399 399 399 399 399 399 399 420 253 234 132 325 325 325 325 325 325 255 372 325 325 133 325 325 133 325 325 325 325 332 332 332
= =
=
A
A
A A
-0.20
= 1-01 A =
=
03 .0
3 44 2.57 2.50 1.61 2.30 1.99 2.18 0.98 1.14 0.04 1.70 1.46 1.66 -1.43 1.92 0.98 0.81 1.30 1.20 -2.26 -0.82 3.66 3.66 3.68 3.51 -1.15 -2.41 2.31 0.96 0.00
1.47 2.57 2-41 2.15 2.30 3.00 3.26 0.98 1.14 1.70 1.46 1.66 -1.43 1.92 0.81 1.30 1.20
= = = =
=
14
= = = = = =
8
-2.26
3.66 3.66 3.68 3.57 1.75 -0.51 -0.86 0.17
14
C9H1003 C9H1003 C9H1003 C9H1003 C9H1003 C9H1003 C9H1003 C9H1003 C9H1003 C9H 10 0 3 5 1 C9H1004 C9H1004 C9H 1 0 0 4 C9H1004 C9H1004 C9H1004 C9H1004S 1 C9H1005 C9H100551 C9H100551 C9H l l 8 R l C9H11CL1 C9HllCL3N103Pl C9H11Fl C9HllFlN205 C9HllIl C9HllNlOl C9HllNlOl C9H 11N l 02 C9H11 N l O 2 C9HllN102 C 9 H l l N l 02 C9H 11N102 C9HllN102 C9Hl l N l O 2 C9HllN102 C9HllN102 C 9 H l l N I02 C9HllN102 C9H1 l N l O 2 C9HllN102 C9H11N l O 2 C9HllN102 C9HllN102S1 C 9 H l l N103 C9H 11N 1 0 3 C9HllN103 C 9 H l l N103 C9HllN103 C9H11N104 C9H12 C9H12
P-HYOROXYBENZO I C ACI 0 1 ETHYL ESTER M-METHOXYPHENYLACETIC ACID P-METHOXYPHENYLACETIC ACID P-HETHOXYPHENYLACETIC ACID H-METHYLPHENOXYACETIC ACIO 0-HETHYLPHENOXYACETIC ACID P-METHYLPHENOXYACETI C ACID P-METHYLPHENOXYACETIC ACID P-METHYLPHENOXYACETIC ACID PHENOXYACET I C AC IOt 3-METHYLTHI 0 GLYCOL SALICYLATE PHENOXVACETIC ACIOv2-METm3XY PHENOXYACETIC ACIDv4-HETHOXY PHENOXYACETIC AC 1013-METHOXY PHENOXYACETIC ACIOI~-METHOXY PHENOXY ACE1 I C A C 1DI 3-HETHO X Y H-HETHYLSUL FONYLPHENYLAC E T I C A C I D BENZOIC A C I O ~ 4 - H Y D R O X Y ~ 3 ~ 5 - O I M E T H O X Y IME-SYRINGATEI PHENOXYACETIC ACI0.M-METHYLSULFONYL PH ENOXYACET I C AC 105 M-M THY LSULFONYL PROPYL BROH I O E t G-PHENYL PROPYLCHLOR l0E1 G-PHENYL ETHYLPHOSPHORAMIOATEIO-MEIO-(~~~~~-TRICLPHENYLI PKOPYLFLUORIOE~G-PHENYL 2'-OEOXY-5-FLUOROURIOINE 127640) PROPYL IOOIOEIG-PHENYL 0-ACE1 AM I OOTOLUENE PROP ION A M I DE, 3-PHENYL ACETANILIOE~P-METHOXY/METHACETIN/ ACETANILIOEtP-METHOXY/HETHACETIN/ 0-AMINOBENZOIC ACIOIETHYL E S T E R P-AMINOBENZOIC ACIDIETHYL ESTER P-AMINOBENZOIC ACIOIETHYL ESTER E T HYLC ARB AM AT E t N-P HENY 1 ET HYLC AREAMATE
6
6
31 31 52 52 60
-.5 02
0.17 0.98 1.02 -2.52 -2.16 -1.85 -1.89 2.49 2.92 1.36 0.95 0.12 -0.51 0.98 -1.20 -0. 80 -0.92 0.74 0.89
= =
C9H12N201 C9H12N2Ol C9H12NZOl C9H12N201 C9HlZN201 C9H12N201 C9H12N2 025 1 C9H12N202S1 C9H12N202Sl C9HlZN203 C9H12N203 C9H12N203 C9Hl2N203 C9H12 N2 03 C9H12N206 C9H12N206 C9H12N403 C9HlZOl C9H 1 2 0 1 C9H1201 C9H1201 C9HI201 C9HlZOl C9H1201 C9HlZOl C9H1201 C9H1201 C9H1201 C9H1201 C9H1201 C9H1201 C9H1201 C9H1201 C9H1201 C9H1201 C9H 1 2 0 1 C9H1202 C9H1202 C9H1202
27
1.02
1
1
1 1 1
1
1
37 36
2.97 2.85 3.02 0.95 0.69 0.87 0.84 0.84 -1.62 -1.79
N
A
*
N A
12
07 .3
0.14 0.97 1.01 1.02 1-06 1.88 0.08 0.83 1.18 1.08 0.86 0.77 0.81 0.97 0.94 1.24 0.63 2.37 1.65 2.03
1.88
2.29 2.94
NO. 3401 3402 3403 3404 3405 3406 3407 3408 3409 3 4 10 3411 3412 3 4 13 3414 3415 3416 3417 3418 3 4 19 3420 3421 3422 3423 3424 3425 3426 3421 3428 3429 34 30 3431 3432 3433 3434 3435 3 4 36 3437 3438 34 3 9 3440 3441 3442 3443 3444 3445 3446 3447 3448 3449 3450 3451 3452 3453 3454 3455 3 4 56 3457 3458 3459 3460 34tl 3462 3463 3464 3465 3466 3461 3468 34b9 3410 3471 3472 3473 3474 3475 3476 3477 3478 3419 3480 3481 3482 3483 3484 3485 3486 3487 3488 3489 3490 3491 3492 3493 3454 3495 3496 3457 3448 3499 3500
SOLVENT
REF FOOT NOTE
LOGP SOLV -1.17 1.78
LOGP OCT
EMPIRICAL FORMULA A A C9H1202 C9H1202 C9H1202 C9H1203 C9H1203 ~ 9 ~ 1 2 0 3 C9H1203 C9H1204 C9H138102 C9H13CLlN201 C9H13N1 C9H13N1 C9H13N1 C9H13N1 C9H13N1 C9H13NI C9H13N1 C9H13N1 C9H 13N1 C9H13N1 C9H13N1 C9H 1 3 N1 C9H13N101 C9H13N101 C9H13N101 C9H13N101 C9H13N104 C9H13N301.M3P04 C9H13N305 C9H13N305 C9Hl3N305 C9H13N5 C9H13N501 C9H148R1 N1 C9H148RlN1 C9H14CLIN1 C9H14NZ C9H 1 4 N2 C9H14N2 C9H14NZ C9H14NZ03 C9H 14N2 0 3 C9H14N203 C9H 14NZ 03 C9H14N203 C9H14N203 C9H14N203 C9H14N203 C9H14N203 C9H14N308PI C9H14N308Pl C9H14N308Pl C9H14N308P1 C9H14N402Sl C9H140151 C9H1401SI1 C9H1402 C9H1406 C9H1406 C9H1406 C9H1407 C9H1407 C9H14SIl C9H158102SIl C9H 1 5 N 1 0 2 C9H 15N102 C9H l 6 C L l N 3 0 2 C9H16CL 1N302 C9HlbN103 C9HlbN202 C9H16N401S1 C9H16N401S1 C9H16NCOlSl C9H1604 C9H1604 C9H1604 C9H1604 C9H1604 C9H17N1 C9H17 N 1 0 3 C9H17N104 C9HI811N102 C9H18N204 C9H18N2S1 C9HlBN6 C9H1806 C9H18 06 C9H19N101 C9H2011N1 C9U20 11N 1 C9HZON201 C9H2ON202 C9H2ON202 C9H21N1 C9H21N 1 C9UZlN3.2.HZS04 C9H2 1 0 4 P 1 C9H2104 P 1 C9H22 I 1 N 1 C9H22N2
NAME
DIETHVL ETHER OILS PARAFFINS OCTANOL OILS PARAFFINS OCTANOL DIETHYL ETHER BENZENE OCTANOL CHCL3 N-HEPTANE N-HEPTANE N-HEPTANE DIETHYL ETIER OIETHYL ETkER XYLENE XYLENE DIETHYL ETtER OCTANOL OCTANOL CYCLOHEXANE CHCL3 N-HEPTANE CHCL3 N-HEPTANE HEXANE OCTANOL OCTANOL N-BUTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL CHCL3 I-PENT. ACETATE CCL4 OCTANOL CHCL 3 OILS BENZENE I-PENT. bCETATE CCL4 OCTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL OCTANOL DIETHYL ETHER OCTANOL OILS 01 ETHYL ETkER OILS OILS DIETHYL E l l - E R OILS OCTANOL BENZENE OCTANOL OCTANOL OCTANOL OECANOL OCTANOL OILS OC TANOL OCTANOL OCTANOL OCTANOL DIETHYL ETkER DIETHYL Ell-ER CHCL3 I BLT ANOL OCTANOL OILS N-BUTANOL CHCL3 OCTANOL PARAFFINS OCTANOL CHCL3 CHCL3 OILS CHCL3 CHCL 3 DIETHYL E l l - E R 01 ETHYL E T + E R DIETHYL ETi-ER OCTANOL TOLLENE OCTANOL CCL4 HEXANE O C 1ANOL DIETHYL ETI-ER
323
327 327
-0.91 2.80
1.53 2.13 0.70
01METHYLGUAIACOL PHENOL~Z-METm)XY-4-ETHYL/P-ETHYLGUAIACOL//
PHENOLS2-METHOXY-CETHYL/P-ETHYLGUAXACOL/ BENZENE. 1,2,3-TRIMETHOXY PHENOL q 2~6-OlHETHOXY-4-METHYL PHENOL q 2 1 6-0 IM ETHOXY-4-METHYL PH ENVL GLY CEROL BENZYLALCOHOL~3r5~OIMETHOXY~~HVOROXY/SYRINGYL ALCOHOL/ PHENVLBORONIC A C I D I Z ~ ~ ~ ~ - T R I M E T H V L M N1-PROPY LN I COT I N A I OE CHLOR IO AMPHETAMINE AM PHET A M I N AMPHETAMINE BENZVLOIMETHYLAMINc BENZYLETHYLAHINE BENLYLETHYLAMINE BENZYLETHYLAMINE ETHYL AMINES l-METHYL.2-PHENYL PHENYL-I-PROPYLAMINE PROPYLAMINEq3-PHENYL N-PROPYLANIL I N E O-TOLUIOINEIN~N-D~METHYL NOREPHEDRINE NOREPHEDRINE NO RPSEUDOE P HE O I NE R NORPSEUOOEPHEORINE ACIO~2*3-OI-H-2-MEFURANYL ESTER N-ME-N-ACETYLCARBAMIC I P R O N I A Z I D PHOSPHATE 1-8-0-ARABINOFURANOSYLCYTOSINE H C L l 6 3 8 7 8 1 l P K A = 4 . 2 1 1 CYTIDINE CYTOSINE ARABINOSIOE (63878) ADEN I N E t 9-BUTYL ADEN INE.9-I 1-HYOROXYME THYL-PROPYL) BUTYLPYRIOINIUM B R O M I D E PHENVLTRIMETHYLAMHONIUM B R O M I D E 3-PHENYLPROPYLAMINE HYOROCHLORIOE Nt N-OIMETHYL-2-( 3-PYR I D Y L )THYLAMINE N- ETHYL-2-1 3-PYR IDYL I E THYLAMINE
1.20
1.53
238
327 327 238 323 311 373 396 138 396 421 46 3 74
=
A
1.04
0.15 0.70 -0.45 0.35 -1.43 2.17 0.53
=
A
-0.28
-1.43
31
31 44
1.63
02 .8
1.57
1.08
1.82
1.92 2.37
B
B
12 .1
1.72 0.96
46
422 374 255 312 331 396 396 396 396 376 283 227 420 227 397 397
B
8
1.60
1.08
1.83 2.45 2.95 -1.45 -3.00
1.60 B 1.83 = 2.45 =

-1.46 -1.07 0.37 -2.13
31 31 31 31
8
B
-1.00 -2.00
1.53 0.37 -2.13 -0.97 -0.79 1.25 0.14 -2.69 -2.07 -1.09
65
37
= =
-1.86
-0.79 1.25 0.14 -2.69 -2.01 -1.09
65
65 268 341 341 341 341 399 399 399 399 399 345 399 399 399
53 46 46 60 60 60
0.82
0.54 0.90 0.82 1.54
60
1 1
= = = = = = 0.82 = 0.54 = 0.90 = 08 .2 =

1.09 1.18 0.23 0.97 0.77 1.07 0.80
N-PROPYL-3-13-PYRIOYLlMElHYLAMINE N-I-PROPYL-3-PYRIOVLMETHYLAMINE
B&R&ITURIC A C I 0 1 5 r ~ - O I E T H Y L I ~ - M E T H Y L / H E T H A R B I T A L / BARBITURIC A C I D ~ 5 r 5 - 0 I E T H Y L ~ l - M E T H Y L / M E T H A R 8 I T A L / BARBITURIC A C I O I 5r 5-OIETHYL. l-HETHYL/MElHARBITAL/ BARBITURIC A C I O t 5 - E T H Y L - 5 - I - P R O P V L / P R O E A R 8 I T A L / BARBITURIC ACIOv 5-ETHYL-5- I-PROPVL/PRO8ARBITAL/ BARBITURIC A C I O I ~ - E T H Y L - ~ - I - P R O P Y L / P R O ~ A R ~ I T A L / BAR8ITURIC A C I O ~ 5 - E T H Y L - 5 - I - P R O P Y L / P R O 8 A R 8 I T A L / BARBITURIC ACID. 5 - E T H Y L - 5 - I - P R O P Y L / P R O B A R B I T A L / BARBITURIC A C I 0 ~ 5 - E T H Y L - 5 - I - P R O P Y L / P R O B A R 8 I T A L / C Y T I D Y L I C ACID CYTIDYLIC A C I O C Y T I O Y L I C ACiO CYTIOYLIC ACID 6-l2-PENHYDROPYRANYL)-4-AH-3-METHIO-l~2~4-TRIAZINONE A- CY CL OH EXYL T H IO ACR YL I C AC IO PHENOL P- IT R IMETHYL S I L YL ) SORBIC ACIOtPROPYL E S T E R GLYCERYL TRIACETATE GLYCERYL TRIACETATE GLVCERYL T R I A C E T A T E TRIMETHYL CITRATE TRIHETHYL CITRATE SILANE, PHENYL-TRIMETHYL PHENYLBORON I C ACID, P-TR IMETHYLS I L I C Y L N- BUTY R O Y LCYCLOBUT ANEC ARB0 XAN I O E N- I-BUT Y ROYLCYCLOB UTAN EC AR 80 XA M I DE 1- I2-CLET1-3-CYCLOHEXYL- 1-NI TROSOUREA( 1 9 0 3 1 )
1.31
03 .1
0.97
=
N A A N
0.20
181 181
181
181
134 423 186 347 3 2 2 14 3 2 298 311 348 348 221 289 80 168 134 134 134 5 212 194 194 4 235 290 377 424 218 241 226 425 425 292 424 424 3 378 378 218 68 260 426 426 297 3
-0.14 1 -0.58 1 0.95 1 -1.21 10 0.40 1 0 -0.15 0.43 10 1 8 -0.15
08 .1
-0.85 0.40
0.38
2.63 3.84 1.94 0.15 -0.36 -0.52 -0.37 -1.33 4.72 1.52 0.41 0.26 2.83 2.69 1.40
0.38 2.42 3.84 2.96 0.25 0.14
=
A
= A
A 8 8 A A
0.01 -0.21
0.03 4.72 0.41 0.26 2.83 1.40 0.25 1.85 2.06 2.12 1.57 1.17
=
= =
=
=
8
1-~2-CLETl-3-CYCLOHEXYL-l-NITROSOUREAll9O37l
UREAI 1.3-OIBUfYRYL OIPROPYLHYOANTDIN 3-METH IO-4-AMINO-6- I-PENT-1 t 2.4-TR I A Z I NE-5-ONE 3- I-PRTHIO-4-AMINO-6I-PR- l r 21 4-TR I A Z I NE-5-ONE 3-N-PRTHIO-4-AMINO-6-I-PR-lr214-TRIAZ(NE-5-ONE AZELAIC ACID AZELAIC A C I O AZELAIC A C I O AZELAIC ACID AZELAIC ACID METHYL-I-PROPYL-~1~1-OIMETHYLPROPYN-3-YLlAMINE 01 ETHYL ACETURETHANE/DETONAL/ AC ETYLCARNI T I N E N-HETHYL4-ACETYL P I P E R I O I N E HETHIODIOE MEPROBAMATE N-HEXY L ETHYL EN ETHIOURE A HEXAMETHYLMELAMINE 1 1 3 8 7 5 1 GLUCOSE~~I~~~-TRIMETHYL A-METHYLGLUCOSIOEI 213-0It4ElHYL N t N-OIETHYLVALERAHIDE 1 1 2 1 6-T R I M E T HYL P I P ER I 0 I N E HE TH I OD I DE l r 3 r 5 - T R I M E T H Y L P I P E R l D I N E HETHIOOIDE T E TRAETHYLURE A NqN-OIMETHVLCAR8AMIC ACIDIOIETAHINOETHYL ESTER N-ETHVLCAREAMIC ACIOIDIETAHINOETHYL ESTER TR I PROPYL AM I N E TRIPROPYLAMINE OCTY LGUANI DIUM SULFATE TRIPRJPYLP~~SP~PTE TRIPROPYLPnOSPkATE TRIMErnYL-HEXYL-AMMONIUM IODIDE PENTANE, 2-AM INOI 5-DI ETHYLAMI NO
-0.23
1.85 2.06 2.12 1.57 1.20 0.97 -0.58 1.66 2.29 0.26 -0.74 -3.76 0.70 -0.07 2.63 -1.92 -1.51 0.16 -3.05 -2.94 1.04 -0.92 -1.08 2.79 2.52 -0.88 1.86
= = =
A A A
12 12 67 46
1.00
0.71 1.83 2.29 1.43 -1.56 0.70 2.63 -1.19 -0.80 1.87 1.79 0.13
=
A
= =
N N A
46 46 44 44
-.1 00
2.79 2.41 2.53 -1.84 0.65
8 8 B
=
B
-0.8E =
N
0.88
46 -1.84 -0.24
=
8
. 590 Chemical Reviews, 1971, Vol. 71, No. 6
NO.

EMPIRICAL FORMULA
SOLVENT I-BUTANOL OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE HEXANE HEXANE CYCLOHEXANE CYCLOHEXANE CY CLOHEXAN E OCTANOL HEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCT ANOL CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE OCTANOL OC T ANOL CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 0 C T ANOL CYCLOHEXANE OCTANOL 0 1 ETHYL ETFER CYCLOHEXANE DIETHYL ETFER CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTPNOL OCTANOL OCTANOL CYCLOHEXANE BENZENE PARAFFINS BENZENE PARAFFINS OCTANOL OCTANOL OCTANOL OCTANOL CHCL3 CHCL3 N- e UTANOL N- B Li TAN OL TOLUENE TOLUENE PRIM. PENTANOLS PRIM. PENTANOLS I-PENT. ACETATE I-PENT. 4CtTATE CCL 4 CCL4 ME- I-BU7.K ETONE ME- 1-BUT.KETONE 0-CICL. @ENZENE
REF FOOT NOTE 4 206 141 206 304 304 304 141 304 27 27
LOGP SOLV 1.08 5.18 2.84 3.91 2.28 2.45 2.71 2.56 1.97 2.03 2.26 2.12 1.79 1.82 2.10 2.15 1.91 5.05 4.60 1.20 1.22
LOGP
oc T
NAME PENTANE, 2-AHINO. 5-OIETHYLAHI NO WINOXALINE I H I O A Z O L E ~ 2 - T R I F L O R O H E ~ 5 ~ 7 - O I C L 1~4-NAPHldOQUINONE~213-D1BRan0 W I N O X A L INE IHIOAZOLE~2-TRIFLOROMESC-CL HALONONITRILEt 3.4-OICHLOROBENZAL HALONONITRILEI 2. bOICHLOROBENZAL HALO NO NIT RILE^ 21 4-OICHLOROBENLAL lrC-NAPHTHOQUINONEt2I3-DICdLORO HALONONITRILE~3-8ROHOBENZAL HALONOhI T R I L E t 4-BROMOBENZAL MALONON I T R I L E t 2-BROHOBENZAL ~~~-NAPHT~OQUINONEI~-BROHO HALONON ITRILE, 3-CHLOROBENZAL HALONONITRILE* 4-CHLOROBENZAL HALONONITRILEv 2-CHLOROBENZAL l r ~-NAPHTHOQUINO~EI 2-CHLORO 1~4-NAPHTHOOUINOhE~2-ChLORO HEPTACHLOR HEPT AC hLOR EPOXl OE HALONON I TR 1L E t 3-FLUOROBENZAL MALONONITRILEe4-FLUOROBENZAL HALONON I T R 1L E, 2-FL UOROBENZAL WINOXALINE IMIOAZOLEI~-TR~FLUOROHETHYL CARBONVL C Y A N I O E I P - T R I F L U O R O M E T H O X Y P H E N Y L H Y O R A Z O N E l r 4 - N A P H T H O Q U I N O N E - 2 - S U L F O N A T E ~ POTASSIUM SALT COUHAR I N , )-CYANO MALONON I T R I L E, 3-N ITROBENZAL MALONOh I TRIL E, 4-N I TROBENZAL MALONONITRILEI~-NITROBE~ZAL 1~4-NAPHlHOQUINONE~2-8ROMO~3-AHIhO lt4-NAPHTHOQUINONEr2-CHLORO-3-AHINO 1~4-NAPHTH0QUINONE~2-ChLORO~3-AMINO 8-TRIFLUOROMETrlYLQUINOLIhE
3501 3502 3503 3504 3505 3506 3501 3508 3509 3510 3511 3512 3513 3514 35 15 3516 3517 3518 35 19 3520 3521 3522 3523 3524 3525 3526 3527 3528 3529
1.01 5.18
3.91
=
=
304 30 4
141 304 30 4 304 141 141 317 317 304 304 304 206 299 141 304 304 304
2.15
27
304
141 141 141 216 216 304 304 141 304 238 141 141 218 141 304 304 206 304 141 141 304 349 427 309 428 304 304 141 141 265 186 325 186 359 325 3 304 304 304 141 141 304 2 80 2 80 2 16 216 216 2 80 72 316 72 316 216 216 410 410 412 412 410 410 410 410 410 410 410 410 412 412 410 410 410
3530
3531 3532 3533 3534
3535
3536 3537 3538 35 39 3540 3541 3542 3543 3544 3545 3546 3547 3548 3549 3550 3551 3552 3553 3554 3555 3556 3557 3558 3559 3560 3561 3562 35c3 3564 3565 3566 3567 3568 3569 3510 3571 3572 3573 3514 3515 3576 3577 3578 3579 3580 3581 3582
3583
26
3584 3585
35e6
3587
3588
3589 3590 3591 3592 3593 3554 3595 3596 3597 3558 3599 3600
1.55 3.08 0.87 -1.08 -0.56 -0.07 -0.02 0.30 0.72 2.12 0.41 2.50 2.05 1.41 -1.62 -2.15 -0.06 1.78 1.71 1.26 1.55 1.38 -0.56 -0.53 3.19 -1.01 1.88 -1.90 -1.49 3.20 3.31 3.01 3.45 -3.32 -1.09 1.18 1.18 -0.45 2.98 0.52 2.84 1.77 0.29 -2.00 -3.52 -2.69 -2.58 4.40 4.40 -3.16 1.64 1.53 2.57 2.47 2.60 2.22 2.40 0.99 2.45 0.98 2.20 1.84 2.33 2.41 3.22 3.27 1.92 1.96 2.75 2.77 2.13 2.19 2.61 2.69 2.64 2.73 2.50 2.63 3.00
3.08 -1.08
= =
2.12 2.50 2.05
= = =
1.78 1.71 1.55 1.38 3.19 1.88 3.20 3.45
= = = = =
=
= 3.31 = 3.01 =
0.19 2.98 2.84 1.67
=
A
=
A
-1.63
2.57 2.47 2.60 2.22 2.25 2.20 1.84 2.33 2.41 2.5b 2.57 2.15 2.21 2.67 2.69 2.40 2.47 2.53 2.61 2.34 2.41 2.27 2.45
=
=
=
8
=
= = =
B
8
B
E l
B 8
C9H22N2 ClOH3CL2F3N4 ClOH48R202 ClOH4CL 1F3N4 ClOH4CLZN2 ClOHICL2N2 ClOH4CL2N2 ClOH4CL202 C 10H5BRlN2 ClOH58RlN2 ClOH58RlNZ ClOH5BR102 ClOH5CL l N 2 ClOH5CL 1N2 ClOH5CLlN2 ClOH5CLLO2 ClOHSCLlO2 ClOH5CL7 ClOH5CL701 C l O H 5 F 1N2 C l O H 5 F 1N2 N2 ClOH5F 1 ClOH5F3N4 ClOH5F3N401 ClOH5KlS105 C 10H5N102 ClOH5N302 ClOH5N302 C10H5 N302 ClOH68RlN102 ClOH6CLlN102 ClOHbC L l N l O 2 C1OH6F3 N 1 ClOHbF3N101 ClOHbN2 ClOHbN201 ClOHbN201 C10H602 C1 0 Hb 0 2 C1 0 Hb 0 2 C1 0 HbO2 C10H603 ClOH603 ClOH7CLlN201 ClOH7CLlNZOI ClOH7CL2F3NZ ClOH7FlN201 C10H7N102 ClOH7NlO2 ClOH7N103 ClOH8 ClOH8 C10H8 ClOH8 ClOH8CL2k202 ClOH8N201 ClOH8N202 ClOHBN202 ClOH8N204 ClOHBOl C10H801 ClOH801 C10H801 C10H801 ClOH803Sl ClOH9C L 1N2 0 2 ClOH9CLlk202 C 10 H9CL 1N20Z C1C H9C L2N 1 0 2 ClOH9CLZN102 ClOH9F 1N202 ClOH9Nl ClOH9N1 ClOH9Nl ClOH9Nl ClOH9Nl C10 H9N1 ClOH9Nl C 10H9 N l ClOH9N1 ClOH9Nl C 1 0 H9N10 1 ClOH9NlOl C10 H9 N 10 1 C 10 H9N 1 0 1 C l O H 9 N l 01 C l OH9Nl 0 1 C10 H9 N10 1 C 10H9N 1 0 1 C 10 H9N10 1 ClOH9Nl 0 1 ClOH9NlOl C 10 H9N 1 0 1 C10 H9N101 C l OH9N 10 1 C l OH9Nl 0 1 C10 H9N101 C 10H9N 1 0 1 C10 H9 N l 0 1 ClOH9Nl0 1
4-HYDROXY-7-TRIFLUOROMEThYLQUINOLIhE
HALONONITRILE~BEhZAL 3-HYOROXYBENZALMALONON I T R I L E 4-HYOROXYBENZALMALOVON I T R I L E ls2-NAPdTHOQUINONE 1.4-NAPHlHOQUIhOkE 1.4-NAPHTHOQUINONE 1.4-NAPdTdOOUIhONE ~I~-NAPHTHOOJINO~E~ 2-hYOROXY
lr4-kAPdTdOQUINONE~2-HYOROXY
CYA~OACETAMIOEI~-CHLOROBENZAL CYANOACElAI(IOE~4-CHLOROBENZAL 96-01 ME BENZIMIOALOLE~2-TRIFLUORHETHYL~4r7-DItL~5 CY ANOACETAM I O E I 2-FLUOROBENZAL ~~~-NAP~T~OOUINO~EI 2-AMIkO l r 4 - \ A P H T H O O U I k O h E ~2-AMIh0 COUHARIN.3-CARBAMOYL AZULENE . NAPHTHALENE NAPHTHALENE NAPHTHALENE MALONAMIDEI~I~-OICHLOROBEN~AL CYANOACETAHIOE~BENZAL STYRENE~3-CYANO~B-NITRO~B-HETHYL STYRENEI~-CYANOIB-NITRO~~-HETHVL A-FUR I L 0 I O X I N E 1-NAPHTHOL 1-NAPHTHOL 2-NAPHTHOL 2-NAPHTHOL 2-NAPHTHOL NAPHTHALENE SULFONIC ACID HALONAMIDEI~-CHLORO~ENZAL MALONAMIOEv 3-CHLOROBENZAL HALON A M IOE, 2-CHLOROBENZAL STVRENE~2~4-OICHLOROIB-NITROIB-ETHYL ST VRENE s 3 r ~-OICHLOROI 8-N I TRO. B- ETHY L MALONAMIOE~3-FLUOROBENZAL 2-METHY LOU 1NOL INE 4-METHYLQUINOLINE 6- METHYL OU I NOL I N E 7-HETHYLOUINOL INE 8-METHYLOUINOL INE 8-METHYLOUINOLINE A- NAPHT HVL AM I N E A-NAPHTHYLAMINE 8-NAPHTHYLAMINE 0-NAPHTHYLAM INE 6-METHOXVPUINOLINE 8-METHOXYPUINOLINE 8-QUINOLINOL.2-METHYL 8- W INOLINOLt 4-M ETHYL 8-PJINOLINJL.2-HETHYL 8-QU INOL INOLt 4-METHYL 8-CUINCLINOL,2-HETHVL 8-UUINOLINOLv4-METHYL 8-W INOLINOLi 2-METHYL 8-PUINCLINOLv4-METHYL 8-WlNOLINOLr2-METHYL 8-WINOLINOLv4-METHYL 8-WINOLINOL~ 2-METHYL B-OUINOLINOLI~-HETHYL 8-PU INOL INOL t 2-METHYL 8-OUINOL INOLt 4-METHYL
partition Coefficients and Their Uses

EMPIRICAL FORMULA NAHE
NO. 3601 3602 3603 3604 36C5 36Cb 36C7 36C8 36C9 3610 3611 3612 3613 3614 3615 3616 3617 3618 36 19 3620 3621 3622 3623 3624 3625 3626 3627 3628 3629 3630 3631 3632 3633 3634 3635 3636 3637 3638 3639 3640 3641 3642 3643 3644 3645 3646 36 47 3648 3649 3 6 50 3651 3652 3653 3654 3655 3656 3657 3658 3659 3660 3661 3662 3663 36t4 3665 3666 3667 3668 3669 3610 3671 3672 3613 3674 3615 3676 3677 3678 3619 3680 3681 3682 3683 3684 3685 3686 3687 3688 3689 3690 3691 3692 3693 3654 3655 3696 3697 3698 3699 3700
SOLVENT 0-OICL. F!ENZENE OCTANOL OIETHYL ETI-ER HEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OILS CYCLOHEXANE OCTANOL OCTANOL HEXANE HEXANE 0 CT ANOL 0 1 ETHYL Ell-ER CHCL3 ETHYL ACETATE CLCHZCHZCL OILS OILS OILS CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL DIETHYL Ell-ER CHCL3 CHCL3 CHCL3 CHCL3 BENZENE I- EUTANOL I-PENT. ACETATE CCL4 N B UT ANOL CYCLOHEXANE CHCL3 CHCL3 BENZENE BENZENE CCL4 0 1 ETHYL E l f ER I-BUTANOL O C T ANOL OCTANOL OCTANOL 50%ETHER+500OHF OCTANOL OCTANOL OCTPNOL I-PENT. ACETATE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 OILS HEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OIETHYL ETHER 0 C T ANOL OCTANOL OCTANOL CYCLOHEXANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 HEXANE HEXANE N-HEPTANE N-HEPTANE DIETHYL ETI-ER CHCL3 EThYL ACETATE CLCH2CH2CL OLEYL ALCOHOL ETHYL ACETATE OCTANOL OCTANOL OCTANOL ETHYL ACETATE OCTANOL OCTANOL OCTANOL CYCLOHEXANE
REF FOOT NOTE 410 218 3 376 141 65 141 141 141 141
LOGP SOLV
LOGP OC T 1.41 1.26 -2.64
3.01
1.41
=
A
1.30
46 0.21 2.06 -2.64 2.92 3.19
3.23
4.40 -0.60 3.02 0.67 0.75 2.07 2.43 -0.48 1.18 -2.00 1.95 -1.30 4.50 2.10 2.18 -3.46 2.39 1.66 -0.13 0.67 0.61 0.75 -0.48 1.20 -0.58 2.04 5.28 3.10 3.17 1.66 -0.13 -0.08 -0.32 -0.18 -0.26 -0.45 0.20 -0.07 -0.34 0.02
A
383
141 346
302
391 391 227 306 306 306 306 382
= = =
A A A A A A
12 12 24 24 24
382
382 304 141 134 393 56 3 42 343 326 344 393 343 130 343 343 253 304 429 387 429 387 429
=
= =
A
8 8
63 2 44 63 2 13 2 2 36
-0.08
-0.48 0.06 -0.03 -0.40 0.22 -0.89
8
N
8
A A A A A A A
0.12
0.19 -2.22 0.79 1.50 3.60 3.44 3.15 3.14 2.82 1.18 1.48 0.87 0.98 1.25 0.16 -0.05 2.21 2.82 2.70 2.86 3.45 2.98
-0.00 0.61
4.50 4.32 4.50 4.41 4.27 1.15 1.57 0.87 0.98 1.25 1.20 -0.05 2.21 2.82 2.62 2.86
3
4
10 10
10 125 430 255 309 418 141 141 141 141 394 46
=
=
= = =
=
30 .0
2.00 -0.55 1.48 0.71 0.90
383 376
384 141 141 141 431 384 384
8 A
1.20
0.90 2.33 2.61 2.63
-1.00
1.42 1.50 0.48 1.27 0.88 1.79 1.93 2.04 0.77 0.88 0.55 0.52 -0.19 1.34 -1.49 0.99 1.46 0.84 1.23 0.90 -0.80 1.65 -0.39 2.85 1.41 1.13 -1.02 0.21 0.61 1.25 -1.77 2.67 1.94
10
302 141 141 141 141 141 393 343 393 343 343 343 391 391 416 138 306 306
-0.75 1.42 1.50 0.48
= =
=
63 2 63 2 2 2 14
0.88 1-10 1.08 1.22 1.21 0.60
=
N N A
306
306 406 432 341 430 218 432 276 430
0.95 0.48 1.70 3.42 1.46 1.13 -1.02 0.21 0.60 1.25
A
A
60
4t
= = = =
46
-1.17
2.67
=
=
141
141
C l O H 9 N l 01 ClOH9N102 ClOH9N102 C lO H 9 N l 0 2S 1 ClOH9N104 ClOHlOBRlNl ClOH108RlN103 C 1 OHlOC L 1N 1 0 2 ClOHlOCLlN102 ClOHlOCLlNlOZ ClCHlOCLlhlO3 ClOHlOCLlN103 C 1On1 O C L 1h 1 0 4 C 1OHlOC L 1N104 ClOHlOCL304Pl C 1 0 H1OC L 3 0 4 P 1 ClOHlOF3N205 ClOH1OI1N106S1 C1OH1OI1N106S1 ClOHlOIlNlO6Sl C1OH1011N106Sl ClOH101203 C10 H 1 0 I 2 0 4 ClOH101204 ClOHlONZO2 ClOHlON204 C lOHlON401S 1 ClOHlON402Sl ClOHlON402Sl ClOH1ON402Sl ClOHlON402Sl ClOHlON402Sl ClOH10N402Sl ClOHlON402Sl ClOHlON402Sl ClOHlON402Sl ClOHlON402S 1 ClOHlON402Sl ClOHlON6 ClOHlOOl C10H1002 ClOH1002 ClOHlOO2 ClOHlOO2 C10H1002 C10H1004 C10H1004 C10H1004 C10H1004 ClOH1004 ClOHllBRlN203 ClOHllCLlN2.H3PC7 ClOHllNl ClOHl I N 1 ClOHllN102 ClOHllNlOZ C10 H 1 1N 1 0 2 C l O H l l N 102 C l O H l l N 102 ClOHllN103 ClOHllNlO3 ClOHllN103 ClOHllN103 ClOHllN103 ClOHllN103 ClOHllN103 ClOHllN104 ClOHllNlO4 C10HllNlO4 ClOHllN104 ClOHl1N104 ClOHllN104 ClOHllN104 ClOHllN104 ClOHllN104 ClOHllNlO4 ClOHllN303Sl ClOHllN303S1 ClOHllN303S1 ClOHllN303Sl ClOHllN303Sl ClOHllN303Sl ClOHl2CLlNlO2 C10 H l 2 C L 1N 1 0 2 ClOH12CL1N103 ClOH12F3N1 ClOH1211N105Sl C10H1211N105Sl C10H1211h105Sl ClOHl21 lNlO5S 1 tlOHl2N102Sl C10H12N2 ClOHl2N2 ClOH12NZ.H3P04 ClOHl2N2Ol ClOHlZN2Ol C10H I 2 N2D 1 ClOH12N201.H3P04 ClOH12N202 ClOHlZN202
8-QU INOLINOLI~-METHYL I N W L E - 3 - A C E T I C ACID C I N DOL E 3- A C ET I A C I D N-METHYLCARBAM I C AC IOt4-BENZOTHI ENYL E S T E R STYRENEI~~~-OIOXYMETHYLENEIB-NITRO~~-METHYL N-METHYLPUINOLINIUM BROMIDE STYRENE~~-~ROHOI~-METHOXY~B-NITRO~~-METHYL STYRENE~~-CHLOROIB-NITRO~~-ETHYL STYRENEIZ-CHLOROIB-NITRO~~-ETHYL STYRENEI~-CHLORO~~-NITRO~~-ETHVL P-AMINOPHENYLACETIC ACI0.N-CHLOROACETYL STYRENE, 5-CHLOROs 2-METHOXYe8-NI TRO18-METHYL PHENOXYACETIC A C I O ~ 3 - A C E T A M I O O - 4 - C H L O R O PHENOXYACET I C AC I O , 3-ACETAMI 00-4-CHLORO 2-CL-1-(2,5-0ICLPHEYYL I-YINYLPHOSPHATE 10.0-01ME 2-CL-1-(2~4-OICLPhENYL~-VINYLPHOSPHATE~O~O-OIME 2~-OEOXY-5-TRIFLUOROMETHYLURIOINE~755201~PKA~7~95l N-(P-I0008ENZENESULFONYLlASPARTIC A C I O N- ( P - I OOOBENZENESULFONYL I ASPARTIC AC I O N- ( P - I 000 BEN ZENESULFONYL IA SPAR1 I C AC I O N- ( P - I OOOBENZENESULFONYL IA SPAR T I C A C I D BENZOIC A C 1 0 ~ 4 - O H ~ 3 ~ 5 - 0 1 - 1 0 0 0 I P R 0 P Y L ESTER ESTER BENZOIC ACID, 3 9 5 - O I - I O O O - C O H ~ 8 - O H - P R O P Y L 8ENZOIC A C 1 0 ~ 4 - 0 H ~ 3 r 5 - 0 1 - 1 0 0 0 1 G - O H - P R 0 P Y L ESTER MALONAMIDEvBENZAL S T YRENEt 4-N ITROI 8-N ITROt 8-ETHYL 3-METH10-4-AMINO-6-PHENYL-lr2r4-TRIAZINE-5-ONE SULFAOIAZ INE SULFAOIAZINE SULFAOI A Z INE SULFAOIAZINE SULFAOIAZ INE SULFAOI AZINE A SU LF A0 I Z INE SULFA0 I Z I N E A A SULF A0 I Z I NE SULFADIAZINE SULFAOIAZINE NE 4.6-01 AMINO-5-PHENYLAZOPYR I H I O I METHYL STYRYL KETONE 8ENZOYLACETONE BE NZOY L A ETONE C
BENZOYLACETONE
BENZOYLACETONE BENZOYLACETONE BENZYLMALONIC ACID BENZYLMALONIC A C I O PHENOXVACETIC ACIO.4-ACETYL PHENOXYACE1 I C A IO 9 3-AC ETYL C C PHENOXYACET I C A 10.2-ACETYL BAR81 TUR I C A C 101 5-ALLYL-5-( 2-BROHALLYL I 5-CHLOROTRYPTAMINE PHOSPHATE 8ENZENEt 3-CYANO-1-PROPYL INDOLEI 1,2-DIHETHVL P-AMINOBENZOIC ACIDvALLYL ESTER BENZENE, 2-NITRO-1-BUTENYL STYRENEvB-ETHYL, 8-NITRO STYRENEI~-METHYLI~-NITRO~~-METHYL STYRENEI~-METHYLI~-NITRO~~-HETHYL P-ACETOXYACETANILIOE P-AMINOPHENYLACETIC ACI0.N-ACETYL N-METHYL-N-ACETYLCAR8AMIC ACIOsPHENYL ESTER N-METHYL-3-ACETYLPHENYLCAR8AMATE ST YRENE14-METHOXYv 8-N I R O t 8-METHYL T STYRENE, 2-HETHOXY+ 8 - N I TROI 8-METHYL STYRENEI~-HETHOXYS ~-NITROIB-HETHYL BENZOYLS ER I N N-HETHYL-3-CAR8OMETHXYPHENYLCAR8AMATE N-METHYL-4-CAR8OHETHOXYPHENYLCAR8AMATE PHENOXYACETIC ACIOpM-ACETAHIOO PHENOXY ACE1 I C AC IO 9 M- AC ETAH I 00 STYRENE, 3r4-OIHETHOXY~B-NITRO STYRENEI~~~-OIHETHOXY~~-NITRO STYRENEIZI~-OIMETHOXYI 8-NITRO STYRENE, ZI~-DIMETHOXYIB-HITRO STYRENE, 4-HYDROXY. 3-METHOXY t 8-N1 TRO p 8-HE THYL SULFAM ETHOXAZOLE SULFAMETHOXAZOLE SULFAM ETHOXAZOLE SU LFAM ETHOXAZOLE SULFAHETHOXAZOLE SULFAMETHOXAZOLE N-HETHYL C A R B A M A T E I ~ ~ ~ - D I W E T H Y L I ~ C H L O R O P H E N Y L N-HETHVL CARSAHATE* 3 r 5-0 IMETHYLI~-CHLOROPHENVL P- AM 1NOS AL I CYL I C A C I O , 3-CHLDROPROPY L E STE R NORFENFLURAMINE N IP-IOOOEENZENESULFONYL )THREONINE N- (P-I OOOBENZ ENESULFON YL I THR EON I NE N-(P-IODO8ENZENESULFONVL )THREONINE N-(P-IOOOBENZENESULFONVL ITHREONINE N-TRICLMETHIO-4-METHYLHEXAHYOROPHTHAL[ MIOE 3-~2-AMlNOETHYL)INOOLE/TRYPTAMINE/ 0 1 HYORON ICOTYR I N E TRYPTAMINE PHOSPHATE 5-HYOROXV-3-( 2-AMINOETHYLI INDOLE 5-HYOROXY-3-~2-AMINOETHYL)INDOLE 2-(G-HYOROXVPROPYL 1-8&-4ZIMlOAZOLE 5-HYDROXYTRYPTAMINP PHOSPHATE ST YRENEp 4-0 IMETHYLAM I NO-8-N I TRO STYRENE~4-OlMETHVLAMINOp8~NITRD
NC. 3701 3702 3703 3704 37c5 3706 37C7 37C8 37C9 3710 3711 3712 3713 3714 3715 3716 3717 3718 3719 3720 3721 3722 3723 3 7 24 3725 3726 3727 3728 3729 3730 3731 3732 3733 3734 3735 3736 3737 3738 3739 3740 3741 3742 3743 3744 3745 3746 3747 3748 3749 3750 3751 3752 3753 3754 3755 3756 3757 3758 3759 3760 37tl 3762 37t3 3764 3765 3766 3767 3768 3769 3770 3771 3772 3773 3774 3775 3776 3777 3778 3779 3780 3781 3782 3783 3784 3785 3786 3787 3788 3789 3790 3791 3792 3793
3754
SOLVENT OCTANOL CHCL3 OILS OILS OILS BENZENE I-PENT. ACETATE CCL4 OLEYL ALCOHOL MIXED S O L V l l 50ZETHER+50ZOUF HEXANE CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 N-HEPTANE OCTANOL OCTANOL OCTANOL N-BUTANOL N-BUTANOL CVCLOH EX AN E CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OILS OILS PARAFFINS OILS OILS
REF FOOT NOTE 399 399 345 296 168 399 399 399 82 433 125 391
LOGP SOLV 1.19
LOGP OCT 1.19 0.89 1.13 1.08 1.13 1.07 1.10 1.05 0.94 1.35 1-10 0.69 0.77 0.76 0.78 -0.60 -0.57 -2.08 -1.79 -2.32 N N A
EMPI R l C AL FORMULA
NAME BARBITURIC ACIOIDIALLYL/OIAL/ BARBITURIC ACIOIOIALLVL/OIAL/ BARBITURIC A C I O V D I A L L Y L / O I A L / BARBITURIC ACIO,OIALLYL/OIAL/ BARBITURIC A C l O ~ O I A L L V L / O I A L / BARBITURIC A C l O ~ O I A L L Y L / O I A L / BARBITURIC A C I O ~ O I A L L V L / O l A L / BARBITURIC A C I O ~ O 1 A L L V L / O I A L / BARBITURIC ACIDSO I A L L Y L / O I A L / BARBITURIC A t 1 0 1 01 ALLYL/OI AL/ BARBITURIC ACID, O I A L L Y L / O I A L / METHVLAZINPHOS/GUiHION/ SULF AETHI DOL E SULFAETHIOOLE DOL E SU LF AET H I SULFAETHIOOL E SULFAETH I DOL E SULF AETHI DOL E 6-MERCAPTOPURINE RIBOSIDE I 4 9 1 1 I NOF URANG YL PKA= 787 9H-PUR I NE- 6 - 1 H IOL 9- 0- 0- ARAB I INOS I N INOSINE XANTHOS INE 4-INOANOLv 1-METHYL 4-INOANOL, 6-METHYL 4- INOANOLI 7-METHYL 4- INOANOL t 5-HETHYL 5-INOANOLv 7-METHYL TR-2-PHENYLCVCLOPKOPYLCARBINOL ACETlC ACIOIB-PHENYLETHYL ESTER P-ETHYLPHENYLACETIC ACID PHENOL t 2-METHOXY-4-ALL VL / E UGENOL/ PHENOL. 2-METHOXY-4-ALLYL/EUGENOL/ A- PHENYL 8UTYR I C A C I O A-PHENYLBUTVRIC ACID 0-PHENYLBUTVRIC ACID 4- PHENYL BUTY R I C AC I O 4-PHENYLBUTVRIC ACID 4-PHENYLBUTVRIC AC IO 0-PHENVLPROPIONIC ACIOIMETHVL E S T E R P-ETHOXVPHENVLACETIC ACID P-hYOROXVBENZOIC ACIO.PROPVL E S T E R PrlENOXYACETIC ACIOv3-ETHVL PHEVOXYACETIC ACID.2-ETHYL PHENOXVACETIC A C I D I ~ - E T ~ V L BARBITURIC ACIO~5-I2-BROHALLVLl-5-I-PROPVL NIN-OI-B-CHLOROETHYLANILINE N-METHYL-1-PHENYLPROPYLAMINE-2 BUTVRAMIOEe4-PHENYL ACETANILIOEI~-ETHOXYIPHENACETIN/ AC ET AN I I O E I 4- ETHO XV/P HENACE T I L N/ AC TAN I IO. 4-ETHOXY/PHENACETI N/ L P- A M I NOBENZOIC ACI 01 I-PROP VL ESTER P-AMINOBENZOIC ACIDIN-PROPYL ESTER P- AMINOBENZO I C I C 101PROPYL E S T E R M-METHOXY-NvN-OIMETHYLBENZAMIOE 0-METHOXY-NIN-OIMETHVL8ENZAMIOE P-METHOXV-NsN-OIMETHYLBENZAMIOE N-METHYL C A R B A M A T E e 3 e 5 - 0 I M E T H Y L P H E N Y L N- METHYL CARBAMATE I 3 9 4 - 0 IMETHYLPHE NYL N-METHYL CAR~AMATEI~-ETHVLPHENVL N-METHYL-2-ETHYLPHENYLCARBAMATE N-METHYL-213-OIMETHYLPHENYLCARBAMATE N-METHVL-~I 5-OIMETHVLPHENVLCARBAMATE N-METHYL-3-ETHVLPHENVLCARBAMATE N-METHVL-3e 4-DIMETHYLPHENYLCAR8AMATE N-METHYL-3.5-OIMETHVLPHENVLCARBAHATE N-METHYL-4-ETHYLPHENYLCARBAMATE N-METHYL CARBAMATEp ~ - M E T H Y L I ~ - M E T H V L T H I O P H E N V L N-METHVL-3-METHYL-4-METHVLTHIDPHENYLCARBAMATE P-AMINOSALICYLIC AClOvN-PROPYL E S T E R N-METHYL-2-ETHOXYPHENYLCARBAMATE N-METHYL-3-ETHOXVPHENVLCARBAMATE N-METHYL-4-ETHOXYPHENVLCAR8AMATE P-AMINOSALICYLIC ACIOI~-HVOROXVPROPYL E S T E R 8-2' - 0 E O X Y T HIOGUANOS I E I 7 1 2 6 1 1 N A-2'-OEOXYTHIOGUANOSINE I 7 1 8 5 1 I ADENOSINE AOENOS INE ADENOSINE W ANOS I N E BENZENE* 1-BUTYL BENZENEI 1-BUTYL CHLORPHENTERMINE CHLORPHENTERMINE PARATHION PARA-OXON AN ABAS I NE ANABAS [NE ANABAS I NE NE AN AB AS I ANABASINE ANABASINE AN A8AS I N E ANABASINE ANABASINE 4-lN-METHYL~-3-PRVIOVL8UTENE-l-VLAMINE NICOTINE N I COT I NE N IWTINE
=
N A A A A
0.33
-0.07 -0.12 -0.07
1 1
-0.35
1.23 0.38 0.38 0.23 1.87 0.49 0.09 -0.66 0.90 -1.27 -2.54 -0.60 -0.57
1 -0.96
ClOH12NZC3 ClOH12N203 ClOH12N203 ClOH12N203 ClOrl12hZC3 ClOH12N203 ClOMlZh203 C10Hl2N203 ClOH12N203
343
415 343 343
44
2 2 2 44
343
415 227 227 277 253 2 53 325 325 325 325 325 56 255 383 327 327 362 385 417 255 361 417 255 383 56 10 10 302 125 227 374 255 186 173 224 418 418 390 276 276 276 391 391 391 384 304 384 384 384 304 384 39 1 384 370 384 384 384 370 227 227 277 2 10 253 253 56 298 396 396 39 2 392 341 434 434 434 434 434 434 434 434 341 341 435 435
14 36
-2.00
-0.92 -1.30 0.97 1.00 1.06 1.21 0.87 1.95 2.30 1.56 1.99 1.34 0.74 1.16 1.06 2.42 0.92 1.17 2.32 0.92
= =
36
1.95 2.30 2.65 2.99 1.89 2.25 2.15 2.42 2.08 2.35 2.32 2.06 2.25 2.65 1.60 2.90 2.16 1.41 1.58 1.58 1.77 2.73 3.10 2.82 1.00 0.71 0.96
=
A A A A A
OILS
OCTANOL OILS OILS OCTANOL OILS OCTANOL OCTANOL OCTANOL CYCLOHEXANOL 50ZETHER+501OMF OCTANOL DIETHYL E T t E R OCTANOL OCTANOL OILS OILS I-PENT. ACETATE I-PENT. ACETATE OLEYL ALCOHOL OCTANOL OCTANOL OCTANOL HEXANE HEXANE HEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL HEXANE OCTANOL N-HEPTANE OCTANOL OCTANOL OCTANOL N-HEPTANE OCTANOL OCTANOL OCTANOL OCTANOL N-BUTANOL N-BUTANOL OCTANOL OCTANOL CHCL3 N-HEPTANE OCTANOL OCTANOL OCTANOL DIETHYL E T k E R CYCLOHEXANE CHCL3 BENZENE TOLUENE CCL4 CLCHZCHZCL PARAFFINS OCTANOL OCTANOL CYCLOHEXANE 'CHCL3
=
A A
=
A
3.04 2.25
2.65 2.55
3.04 =
= =
03 .2
2.90 1.46 1.41 1.58 0.43 0.60 2.81 3.17 2.28 1.00 0.71 0.96 0.56 0.60 0.61 1.93 1.95
=
8
= =
A A
3 3
44
= =
=
1.93 1.95
2.03
2.20 2.09
2.03
2.20 2.09 2.23 2.23 2.47 1.24 1.75 1.63 -0.56 -0.79 -1.10 -1.23 -0.76 -1.79 4.11 4.11 2.26 2.15 1.69 0.97 0.66 0.54 0.76 0.81
= = =
=
C 1 0 H12N402 S2 ClOH12N402SZ ClOH12N40451 C1 0 H I Z N4 04s 1 ClOH12N405 ClOH12N405 ClOH12N406 ClOHlZOl ClOHlZOl C10H1201 ClGHlZOl C 1 0 H120 1 ClOHlZOl C10H1202 C10H1202 ClOH1202 ClOHl202 C10H1202 ClOHlZO2 ClOHl202 ClOHlZO2 ClOH1202 ClOHlZOZ ClOHIZO2 ClOH1203 ClOH1203 C10H1203 C10H1203 ClOHl203 ClOH13BRlN203 ClOH13CLZNl ClOH13Nl ClOHlJNlCl ClOH13N102 ClOH13N102 ClOH13N102 ClOH13N102 ClOH13N102 C lOH13N 1 0 2 ClOH13N102 ClOH13N102 ClOH13N102 ClOHl3NlOZ ClOH13k102 ClOH13N102 ClOH13N102 ClOH13NlOZ ClOHl3NlO2 ClOH13N102
22 .3
2.23 0.62 2.47 1.02 1.24 1.75 1.63 -0.68 -0.56 -0.79 -1.10 -1.23 -0.18
= =
= =
14
= = = = = = = = =
0
14 14
36
36 31 31 60
-0.92
4.11 4.11 2.90 1.24 2.15 1.69 0.97
=
=
=
0 B 0 B
-0.23
-0.58
0.82 03 .0
0.20 -0.01 0.52 -0.60 1.13 1.17 0.25 1-89
3795 3796 3757 3798 3799 3800
60 60
1.13 1.17
1.38 8
C101i13N103 ClOH13N103 Cl O H l 3 N 1 0 4 ClOHl3N503S 1 ClOH13N503SI ClOHl3N504 ClOH13N504 ClOH13N504 ClOH13N505 C10H14 C10H14 ClOHl4CLlNl ClOH14CLlNl ClOH14N105PlSl ClOH14N106Pl C10H14N2 C10H14N2 C10 H l 4 N 2 C10H14N2 ClOH14N2 ClOH14N2 ClOHl4NZ ClOH14NZ C10H14NZ C10H14NZ C10H14N2 ClOH14N2 ClOH14N2
NO. 3801 3802 3803 3804 3805 3806 3807 3808 3809 3 8 lo 3811 3812 3813 3814 3815 3 8 16 3817 3818 3819 3820 3821 3822 3823 3824 3825 3826 3827 3828 3829 3830 3831 3832 3833 3834 3835 3836 3837 3838 3839 3840 3841 3842 3843 3844 3845 3846 3847 3848 3849 3850 3851 3852 3853 3854 3855 3856 3857 3858 3859 38 60 3801 3862 3863 3864 3865 3 8 66 3867 3868 3869 38 70 3871 3872 3873 3874 3875 3876 3877 3878 38 79 3880 3881 3882 3883 3884 3885
SOLVENI BENZENE XYLENE TOLUENE NITROBENZENE N-BUTYL ACETATE CCL4 CLCHZCHZCL N-HEPTANE N-HEPTANE 0-OICL. BENZENE PARAFFINS OCTbNOL OCTANOL OCTANOL N-HEPTANE N-HEPTANE N-hEPTANE N-I-EPTANE N-I-EPTANE OCTANOL N-HEPTANE N-HEPTANE OCTANOL OILS OILS OCTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL OCTANOL N-BUTANOL PRIM. PENTANDLS HEXANOL OCTANOL N-BUTANOL PRIM. PENTANOLS HEXANOL HEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE OC T ANOL CYCLOHEXANE OCTANOL OCTANOL OILS OILS OILS OLEYL ALCOHOL OCTANOL OILS PARAFFINS OCTANOL OCTANOL DIETHYL E T k E R XYLENE OCTANOL CHCL3 XYLENE N-HEPTANE N-HEPTANE DIETHYL TI-ER N-tEPTANE CHCL3 N-PEPTANE O C TANOL 01 ETHYL ETtER CYCLOHEXANE CHCL3 CHCL3 I -BUTANOL N-tEPTANE CHCL3 N-tEPTANE DIETHYL TI-17 CHCL3 OCT ANOL OCTANOL 0 C T ANOL N- @U T ANOL PRIM. PENTANOLS HEXANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL 50%ETHER+SO%DHF OCTANOL OILS OILS 50XETHER+SClDMF OCTANOL OCTANOL N-BUTANOL PRIM. PENTANOLS HE XANOL OCTANOL DIETHYL ETkER CHCL3
REF FOOT NOTE 435 435 435 435 435 435 435 435
LOGP SOLV 0.98 0.75 0.86
LOGP OCT 1.23 1.41 1.25 1.62 1.06 0.80 B B 8
EMPIRICAL FORMULA ClOH14NZ C10H14NZ ClOH14NZ ClOH14NZ ClOH14NZ C10H14NZ C10H14NZ C10H14NZ ClOH14NZ ClOHl4NZ C10H14N2 ClOH14N2 ClOH14N201 ClOH14N201 ClOH14N201 C1 0 H14N2 0 1 ClOH14N201 ClOH14N201 ClOH14N201 ClOH14N202 ClOH14N202 ClOH14NZOZ ClOH14N2OZSl ClOH14N203 ClOH14N403 ClOHl4N507Pl ClOH14N507Pl ClOH14N507Pl ClOH14N507P1 ClOH14N507Pl ClOH14N507Pl ClOH14N507Pl ClOH14N507Pl ClOHl4N508Pl ClOH14N508Pl ClOH14N508Pl ClOH14N508PI C10H1401 ClOHl4Ol C10H1401 ClOH1401 ClOH1401 ClOH1401 ClOH1401 C10H1401 ClOH1401 C10H1401 C10H1401 ClOH1401 ClOH1402 ClOH1402 ClOH1402 ClOH1403 C l OH15C L 1N2D1 CIOHlSN1 ClOH15N1 ClOHlSNl ClOHlSNl ClOHlSNl ClOH15Nl ClOH15N1 ClOH15N1 ClOH15Nl ClOHlSNl ClOHlSNl ClOHl5NlOl ClOHl5NlOl ClOHI5N101 ClOHl5N101 ClOH15N101 ClOHl5NlOl ClOHl5NlOl ClOHlSNlOl ClOH15N101 ClOHlSN102Sl ClOH15N102Sl C10 H15N5 ClOH15N501 ClOH15N5010PZ ClOH15N5010P2 C10 H15 N5010 P2 ClOH15N5010PZ ClOH1503PlSl ClOH1504Pl ClOH16N2 ClOHl6NZ ClOHlbNZ ClOH16N202Sl ClOHlbN203 ClOHlbN203 ClOH16N203 ClOHl6N203 ClOHlbN401Sl ClOH16N5013P3 ClOHl6N5013P3 ClOH16N5013P3 ClOH16N5013P3 C10H1601 C10H1604 C10Hl604
NAME NICOTINE N I COT I NE N I COT I NE NICOTINE NICOTINE N I COT I NE N I 0011 NE NICOTINE N I COT I N E N I COT I NE NICOTINE 3-PYRI DYLMETHYL-N-PYRROLIOI" NIKETHAMIDE 3-PYRI OVLMETHYL-N-HORPHOLINE UREA, ETHYL.H-TOLYLUREA, ETHYL t 0-TOL Y L UREA~ETHYLIP-TOLYLUREAlMETHYLrO-PHENETVLUREA, N-PROPYLPHENYLN-METHYL-3-OIMETHYLAM INOPHENYLCARBAMATE UREA. ETHYL.O-ANI svLUREAr ETHVLIP-ANISYLBARBITURIC A C I O ~ 5 ~ E T H Y L ~ 5 - M E T H Y L A L L Y L ~ 2 ~ T H I O BARBITURIC ACIOI 5-ALLVL-5-I-PROPYL CAFFEINEI ETHOXY 3-AOENYLIC ACID 3-ADENYLIC ACID 3-ADENYLIC A t 1 0 3-ADENYLIC ACID 5-ADENYLIC ACIO 5-ADENYLIC ACID 5-ADENYLIC ACID 5-ADENYLIC ACID GU4NYLIC ACID GUANYLIC ACID GUANYLIC ACID GUANYLIC ACID BUT AN0 L I +PHENYL P-1-BUTYLPHENOL P-T-BUTYLPHENOL P-1-BUTYLPHENOL 2-OECALDNE PHENOL, ~-HETHYLI 5- I-PROPYL PROPAN E, 1-M ETHO XY- 3-P HENY L THYMOL THYMOL THYMOL THYMOL THYMOL CAHPHORPUINONE PHENOL~Z-HETHOXY-4-PROPVL/P-PROPYLGUAIACOL/ PHENOL~Z-HETHOXY-4-PROPVL/P-PROPYLGUAIACOL ~ * ~ - P R O P A N E O I O L I 3-( 2-TOLYLOXY) N1-BUTYLNICOTINAMIDE CHLORIDE BENZYLPRDPYLAM INE 1-BENZYLPROPYLAH INE N-BUTYLANIL INE HETHAHPHETAHINE/DESOXVEPHEDRINE/ HETHAMPHETAMINE/DESOXVEPHEORINE/ METHAHPHETAMINE/DESOXVEPHEORINE/ HETHAHPHETAH INE/DESOXYEPHEDR I N E / N-METHYL-G-PHENYLPROPYLAMINE PHENETHYLOIHETHYLAHINE PHENTERMINE PHENTERHI N E EP HEOR I N E EPHEDRINE EP HE OR I NE EPHEDRINE EPHEDR I N E PI-EDR I N E EPHEDRINE PSEUDOEPHEDRINE PS EUOOEPHEDRINE Ns N-DIETHYLBENZENESULFONAHIOE Nv N- D I E THY L BEN LENE S rlL F 0 NAH I D E ADEN I N E, 9-PENTYL AOENINEI~-(~-HYOROXYMETHYL-BUTYLI ADP ADP ADP ADP 0.0-01 ETHYL-0-PHENYLPHOSPHOROTHIOATE 010-DIETHYL-0-PHENYLPHOSPHATE N-8UTYL-3-PYRIOYLMETHYLAHINE NeN-DIETHYL-3-PYRIOYLHETHYLAMINE 4- IN-METHYL )-3-PYR IDYLBUTYLAHINE 5-S-BUTYL-5-tT-2-THIO8AR8ITURIC ACIO/INAC I N / BARBITURIC A C I O , 5-BUTYL-5-ETHYL BARBITURIC ACI Dq 5- BUTYL- %ETHYL BARBITURIC ACID, 5-ETHYL-5- $-BUTYL BAR81TURIC A C I 0, 5- S-BUTYL-5-ETHYL ~-HETHIO-~-AMINO-~-CYCLOHEXVL-~~~V~-TR~AZ NE-5-ONE ATP AT P ATP AT P AOAHANTANEt 1-HYDROXY CAMPHORIC ACID CAMPHORIC ACID
0.91
0.78 0.94
11 .1
14 0.03 -0.80 1.03
400
435 435 341 2 18 341 419 419 419 419 419 384 419 419 218
60
60
0.05 1.10 0.33

0.04 -0.85 -1.18 -0.89 -1.80 -0.96 1.43 -1.66 -1.55 2.19 0.05 0.24 -0.22 -0.52 -0.10
1.10 = 0.33 =
0.04
1.43 2.19 1.24 0.64
= = =
A B
345
371 181 181 181
10 10 10
18
-0.22
181
181 181 181 181 181 181 181 181 372 56 32 5 325 65 325 255 186 173 82 436
10
10
-0.22 0.28
-0.70 -0.40
0.28
10
18 10 10
-0.30
0.68 -0.10 -0.40 -0.40 0.51 3.31 1.12 1.29 1.97 1.30 2.70 3.30 2.79 2.78 2.65 2.98 0.68
10
18
3.31 1.97 2.70 3.30 3.73 3.72 3.68
= = = =
A A A
82
186 327 327 218 373 374 422 312 396 422 138 396 374 42 1 396 396
3.52
1.52 3.15 1.41 -1.39 2.17 1.96 3.58 2.12 2.23 2.14 2.10 0.93 1.12 0.75 0.10 1.15 0.89
1.52
2.16 1.78 1.41 -1.39 1.49 1.32 3.58 2.75 1.58 1.24 0.71 1.46 1.63 2.71 1.80 0.93
=
P
= =
12 31 31 44 31 31
8 8
8 8
B
8
218
3 357 405 396 4 396 396 396 113 113 397 39 7 181 181 181 181 437 437 341 341 341 125 218 345 345 125 134 31 31 31 31 31
=
8
8
0.30
-0.39 1.05 0.38 1.18
8
8
-3.00
1.30 -1.54 2.22 3.65 1.79 0.66 0.89 -0.52
10 10 10 18 60 60 6C
2.05 4.08 1.79 0.66 0.89
A N
= =
0.85
0.71 3.46 1.64 1.34 1.01 0.91 0.71 1.89 0.41 0.13 0.29 2.14 1- 6 4 0.15 1.04 1.18 2.14 1.45 -1.30 3.46 1.64 1.34 1.01 0.91 2.57 1.89 1.56 1.31 1.52 2.14 1.64
=
=
=
=
3886
3887 3888 38139 3890 3891 38S2 3893 3894 3855 3856 3897 3898 3899 3900
= =
P
=
=
181
181 181 181 218 212 46
10 10 10 18
2.14 1.38 0.04
=
P A

LOGP OCT EMPIRICAL FORMULA NAME CAMPHORIC ACID N-PENTANOVLCYCLO8UTANECAR8OXAMIOE N-I-PENTANOYLCYCLOBUTANECAR8OXAMIOE N-1-PENTANOYLCYCLOBUTANECAR8OXAMIOE 3-MORPHOLINO-4-AMINO~6~I-PR-1~2~4-TRIAZINE~5-ONE (954411 1-~2-CLETJ-3(4-MECYCLOHEXYLl-l-NITROSOUREA QUINUCLIOINOL-+ACETATE METHIOOIOE 0, LI-LY S I N 9 D l AC ETYL 214-TRI AZINE-5-ONE 3-N-BUTYLTHIO-4-AM INO-6-I-PR-1 3-METHIO-4-AMINO-6-N-HEXYL-lrZI4-TRIAZINE-5-ONE SEBACIC ACIO SEBACIC A C I O T R IETHYL EN E GLYCOL 0 I AC ETA TE TRIETHVLENE GLYCOLtOIACETATE TRIETHYLEYE GLYCOLtOIACETATE ETHYLPROPYLACETURETHANE/EPRONAL/ 3-N-eUTYLAM INO-4-AMINO-6-I-PR-1 I 2.4-TRI A21 NE-5-ONE N-HEPTYL ETHYL ENETH IOUR EA N-ALLYLCARBAMIC ACIO~OIETAMINOETHYL ESTER MENTHOL ME NT HOL OECANOIC ACIO DECANOIC A C I O GLUCOPYRANOSIDEI~-T-BUTYL (BETA I GLUCOSEvZt 3149 6-TETRAMETHYL 2 8-METHYLGLUCOSIOE~ 1 3 9 4-TR IMETHYL PROPVLHEXEOR INE PROPYLHEXEORINE N-PROPYLCARBAMIC ACIOIOIETAMINOETHYL ESTER N-I-PROPYLCARBAMIC ACIO~OIETAMINOETHYL ESTER OE CAME T HY L ENE GL Y COL T E T R A E T H Y L E N E G L Y U ) L r O I M E T H Y L ETHER 01-AMYLPHOSPHATE SILANE, OCTYL-DIMETHYL 1.4-N APHTHOQU I NONE s 2 1 3-0 I C HLORO 5- M THYL E 1 ~-NAPHTHOQUINONEI 21 ~-OICHLOROI~-METHYL , 1~4-NAPHTHOQUINONE~2-METHYL~3-8ROMO lr4-NAPHTHOQUINONE~2-BROMO~3-METHOXY ~~~-NAPHTHOQUINONE~~-METHYLI~-CHLORO
NO. 3901 3902 3903 3904 3905 3906 3907 3908 3909 3 9 10 3911 3912 3 9 13 3914 3915 3916 39 17 3918 3 9 19 39 20 3921 3922 3923 3924 3925 3926 3927 3928 3929 3 9 30 3931
SOLVENT XYLENE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL CHCL3 CHCL3 OC TANOL OCTANOL 0 1 ETHYL ETtER CHCL3 DIETHYL Ell-ER OILS OILS OILS OCTANOL PARAFFINS DIETHYL ETVER OILS OILS OCTANOL N-FEPTANE OCTANOL CHCL3 CHCL3 CHCL3 N-HEPTANE 01 ETHYL ETHER DIETHYL ETHER DIETHYL Ell-ER OILS 01-BUTYL ETHER OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE ' CYCLOHEXANE CYCLOHEXANE CHCL3 BENZENE CHCL3 BENZENE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CHCL3 BENZENE OCTANOL OCTANOL PARAFFINS CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OILS OCTANOL OCTANOL DIETHYL ETVER 01 ETHYL Ell-ER CHCL3 CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 OC TANOL OCTANOL DIETHYL ETkER CHCL3 BENZENE ETHYL ACETATE PARAFFINS OLEYL A L c o r o L CHCL3 CCL4 ..CLCHZCHZCL DIETHYL ETkER
REF FOOT NOTE 46 348 348 348 134 227 424 67 134 134 2 12 194
LOGP SOLV -1.81 0.75 0.48 0.53 0.49
33 .0
46 -3.67 -2.90 3.21 2.68 1.76 0.04 -0.28 -1.48 -1.48 0.52 1.78 0.52 -1.20 2.27 2.40 4.09 1.87 1.18
-0.18 0.75 0.48 0.53 0.49 3.30

3.21 2.68 1.65 1.40 -0.13 -0.79 -0.11 1.66 1.78 -0.11 3.25 3.37 4.09 1.18 0.77 1.08 2.65 0.54 0.50 1.27 -1.42 4.02
= =
A A A 8 A A
= = = =
2
2 2 29 0 134 241 378 173 224 2 18 139 438 425 425 396 396 378 378 3 2
=
8 A A
44
31
=
N N
0.20
31 31 44 44 0.52 3.37 2.24 -0.46
8
B 8 A 8
-0.50
1.32 -2.25 0.79 4.02 2.49
3932
3933 3934 3935 3936 3937 3938
ClOH1604 ClOH17N102 ClOH17N102 ClOH17N102 ClOH17N502 ClOH18CLlN202 C10H181 l N l O 2 ClOH18N204 ClOH18N401Sl ClOHl8N4OlSl ClOH1804 Cl O H l 8 0 4 C10H1806 C10H1806 ClOH1806 ClOH19N103 ClOH19N501 ClOH20NZSl ClOH20N202 ClOH2OOl ClOHZOOl C10H2002 ClOHZOOZ C l OH2 006 C1 OH2 006 C l O H20 06 C l O H 2 lN l C lOH2 1N 1 ClOHZZN202 ClOH22N202 C l OH22 02 ClOH2205
2 36
298 141 141 141 141 141
3.06
2.85 2.17 2.61 1.45 1.56 1.85 2.04 2.11 1.46 1.68 1.94 0.30 2.10 2.20 1.82 1.84 1.88 1.87 3.17 2.75 3.17 3.16 0.66 1.35 0.48 1.20 0.79 3.10 2.68 2.45 1.58 -0.33 -0.73 -0.54 -1.10 -0.92 -0.91 2.02 2.65 2.30 2.28 0.83 CllH78R103 C11~7CL102 CllH8CLlN102 CllH8N2 C 1 1 HEN2 CllH8NZ CllH8NZ CllHBN201 C 1l H 8 N Z O l CllH8N201 C l l H8N202 CllH802 ~ 1 1 ~ 8 0 2 C l 1H E 0 2 C11 ti802 C11H802 C11 H802 S 1 C l l H 8 C2S 15 E 1 C1 l H 8 0 2 s l S E l CllH8OZSE2 CllH802SE2 CllH803 CllH803 C l l H803 CllH803 CllH803 CllH803SEl C 1 1 H8 03SE 1 CllH9Nl C l l H 9 N 1C 1 CllHlON2 CllHlON201 CllHlON201 CllHlON202 CllHlON202 CllHlON202 CllHllNl CllHllN104 CllHllN104 CLlHllN301 C 1 1 H 1 1N 3 0 1 CllHllN30251 CllHllN302Sl C l 1 H11N302S 1 CllHllN302S1 CllHllN302SI CllHllN302Sl CllHllN302Sl CllHllN302Sl CllHllN30ZSl CllHllN302Sl CllHl2BRlNl CllH12CL2N205 CllHlZCL2N205 CllH12CL2N205 CllnlZCL2h205 CllHl2CL2h205 CllHlZCL2N205 C11 H l 2 C L 3 N 1 0 2 5 1 CllHl2IlN104Sl C 11H12 I A 1 0 4 s 1 N C l l H l 2 I 1N104S1 CllH121AN105Sl
3939
3940 3941 3942 3943 3944 3945 3946 3947 3948 3949
407
141 304 304 304 304 304 304 141 141 141 141 141 141 141 388 388
5-CHLORO-8-ACETOXYQUINOLINE
MALONONITRILEI A-METHYLBENZAL MALONONITRILEt 2-METHYLBENZAL MALONONITRILES4-METHYLBENZAL MALONONITRILEI 3-METHYLBENZAL MALONONITRILE.4-METHOXYBENZAL MALONONITRILEI 3-HETHOXYBENZAL HALONONITRILEt 2-METHOXYBENZAL MALONON I T R I L E I 3-METHOXY-4-HYOROXYBENZAL ~ ~ ~ - N A P H T H O Q U I N O N E6-METHYL I 1.4-NAPHTHOQUINONEv .?-METHYL 1~4-NAPHTHOQUINONE~6-HETHYL 1.4-NAPHTHOQUINONEv5-METHYL ~~~-NAPHTHOQUINONEI~-METHYL 1.4-NAPHTHOQUINONEt 2-WETHYLTHIO 1-12-SELENOPHEN-YL 1-3( 2-THIENYL I-1.3-PROPANEOIONE 1- (2-SELENOPHEN-YL I - 3 ( 2-THIENYL 1-1 r3-PROPANEOIONE
3950
3951 39t2 3953 3954 3955 3956 3957 3958 3959 3960 396 1 3962 3963 3964 3965 3966 3967 3968 3969 3970 3971 3972 3913 3974 3975 3976 3977 3978 3979 3980 3981 39 82 3983 3984 39e5 3986
2.10 2.20
= =
388
388 304 141 141 141 141 388 388 65 216 439 304 304 304 304 304 2 80 141 141 235 284 393 56 342 113 343 113 393 343 343 343 65
9
4.10 4.07 4.10 4.46
A A A A
lr3-OI~2-SELENOPHEN-YLl-l~3-PROPANEOIONE
l t 3-01 (2-SELENOPHEN-YL ) - 1 9 3-PROPANEOIONE COUMARINI 3-ACETYL 194-NAPHTHOQUINONE, 2-METHOXY 1~4-NAPHTHOOUINONE~Z-METHOXY ~~~-NAPHTHO~UINONEI~-METHYL-~-HYOROXY lr4-NAPHTHOQUINONE~Z-METHYL~3-H'fOROXY 1- ( 2 - S ELENOPHEN-YL 1- 3( 2-FURYL I - 193-PROPANE01 ONE I- (2-5 EL ENOPHEN-YL 1-3( 2- FURYL I 1v 3-PROPANE01 ONE 4- PHENYL PY R IO I NE 6-ACETYLQUINOLINE 2- IP-AM INOPHENYL I-PYR I O I N E CYANOACETAMIOE~Z-METHYLBENZAL CYANOACETAMIOE,4-METHYLBENZAL CYANOACETAYIOE~4-METHOXY8ENZAL CYANOACETAMIOEI~-METHOXY~ENZAL CYANOACETAHIOEI~-METHOXY~ENZAL 2.6-OIMETHYLQUINOL I N STYRENE. 3.4-OIOXYMETHYLENE 18-NITROr8-ETHYL STYRENE~4-METHOXYCARBONYL~8-NITRO~B-METHYL l-PHENYL-3,5-OIHETHYL-4-NI TROSOPYRAZOLE l-PHtNYL-3~5-0IHETHYL-4-NITROSOPYRAZOLE SULF APYR I O INE SULFAPYR IO INE SULF APYR I O I N E SULFAPYR I D I N SULFAPYRIDINE SU LF APY R I DINE SULFAPYRIDINE SULFAPYRIDINE SU LFAPY R I O I NE SULFAPYRIDINE M E l HYLCU INOL I N I U 8ROH 1 DE CHLORAMPHEN ICOL CHLORAMPHENICOL CHLORAMPHENICOL CHLORAMPHENICOL CHLORAMPHEN ICOL CHLORAMPHENICOL N-TR I CL H E T H L 0- 4.5- 0 I W E THYL T E TR AHYORO PH TH AL I H IO E
26
1.35 =
1.20
4.03 4.00 2.45 1.58
=
A A
63
-0.02
0.00 -0.40 -0.26 0.02 0.06 0.04 -0.75 0.35 -2.22
-2.76
2 63 2 2 2 46 12 12 12
3987 35 8 8 39 89 39 90
3991 3992 3993 3554 3955 3996 3997 3998 3999 4000
440 440 440 440 440 406 306

306 306 306
1.14 0.62 -0.65 -1.45 1.52 -1.41 2.93 1.70 -0.18 1.70 0.67
2.28 1.94 -0.02 0.00 -0.23 -0.12 -0.21 -0.18 -0.20 0.03 0.19 0.00 -2.76 1.14 0.67 0.64 0.00 1.57 3.50 2.69 1.69 0.66
=
A
= =
A A 8
B n
8
A
= =
A A
A A
N- ( P - I OOOBENZEN ESUL FON YL IPROL I NE N- (P-IOOOBENZENESULFON YL I H Y O R O X Y PROLI NE
NO. 4001 4002 4003 4004 40C5 4006 40C7 4008 4009 40 10 4011 40 12 4013 40 1 4 40 15 40 16 40 17 4018 4019 40 20 4021 4022 4023 4024 4025 4026 4027 4028 4029 4030 4031 4032 4033 40 34 4035 4036 4037 4038 4039 4040 4041 4042 4043 4044 4045 4046 4047 4048 4049 40 50 4051 4052 4053 4054 4055 4056 4057 40 58 40 59 4060 40tl 4062 4063 4064 4065 4066 4067 4068 4069 4070 4071 4072 4073 4074 4075 4076 4077 4078 4079 40 80 4081 4082 4083. 40E4 4085 4086 4087 4088 40 8 9 4090 '40 9 1 4092 4093 4094 4055 4096 4097 4098 4099 4100
SOLVENT CHCL3 ETHYL A C E T A T E CCL4 CLCH2CH2CL DIETHYL ETkER CHCL3 CLCI'ZCHZCL 0,ILS OILS OILS N-k EPTAN E OC TANOL DIETHYL ETkER CHCL3 CHCL3 CHCL3 CHCL3 OILS OILS BENZENE I-BUTANOL N-HEPTANE N-HEPTANE N-kEPTANE OLEYL ALCOHOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL DIETHYL E T k E R CHCL3 BENZENE I-PENT. ACETATE CCL4 I-BUTANOL I-BUTANOL OCTANOL CHCL3 CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 OCTANOL CHCL3 CHCL3 BENZENE I-BUTANOL I-PENT. ACETATE CCL4 CYCLOHEXANE OC TANOL N-BUTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL 3 CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 ETHVL ACETATE DIETHYL E T F E R CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 BENZENE N-HEPTANE OCTANOL OCTANOL CHCL3 CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 N- I' EPT AN E N-HEPTANE N-HEPTANE CHCL3 CCL4 CLCHZCHZCL CHCL3 CCL4 CLCHZCHZCL OC TANOL OCTANOL
REF FOOT NOTE
LOGP SOLV -0.72 1.65 -2.00 -0.25 1.23 -2.00 -1.15 4.99 5.01 2.35 -4.52 0.23 -1.14 0.88 1.45 1.33 1.45 -1.49 -1.16 -1.05
LOGP OCT 0.55 1.78 0.15 1.25 -0.58 5.72 5.75

A A A
EMPIRICAL FORMULA C l l H l 2 I lN105S1 CllHlZIlNlO5Sl C l l H l Z I 1N105S1 CllH1211Nl05Sl C 11 H12 1 l h l C b S 1 CllHlZIlN106S1 CllhI2IlNlObSl C l l H l 2 I203 C l l H l 2 1203 C 1 1 H12 I 2 0 4 CllHl2N2 CllH12N201 CllHl2NZOl CllHl2NZOl CllHl2N2Ol CllHl2N201 CllHlZN2Ol CllHl2N2Ol CllHlLhZOl CllH12N201 CllHl2NZOl CllHlZh2Cl CllHlZNZOl CllHl2NZOl CllHlZNZOl CllH12N202 CllH12N202 CllH12N202 CllH12N202 CllHl2N202 CllH12N203 CllH12N203 CllH12N203 CllH12N40251 CllHl2N402S1 CllH12N402Sl CllH12N40251 C l l H12N402S1 CllH12N402Sl CllH12N402Sl CllH12N402Sl CllH12N402Sl CllH12N403S C11 H12N403S CllH12N40351 CllH12N403Sl CllH12N403Sl C I 1H12N403S 1 CllH12N403Sl CllH12N40351 CllHlEN403S 1 CllH12N403Sl CllH12N40351 CllH12N40351 CllH12N40351 CllH12N403Sl CllH12N40351 CllHlZN403Sl CllHl202 CllH1203 C 11H13C L l N 2 0 2 CllH13N102 CllHl3NlOZ CllH13h102 CllH13N103 CllH13N103 CllH13N103 C l I H13N103 C l l H13N103 CllH13N104 CllH13N104 CllH13N104 CllH13N104 C11 H13 N 1 0 4 CllH13N104 CllH13N104 CllH13N104 C 1 H13N 1 0 4 1 CllH13N301 CllH13N301 CllH13N301 CllHl3N303S1 C11 H13N303S 1 CllH13N303Sl CllHl3N30351 CllH13N303S 1 CllH13N303S 1 CllH13N303Sl CllH13N303Sl CllHl3N30351 C 11H l 4 C L 1N103 CllH14F3Nl C l l H 1 4 I 1N104S1 CllH1411N104Sl CllH1411N104Sl CllH1411N104S2 C l l H 1 4 I 1N104SZ C 1 1 H 1 4 I 1N104S2 CllHl4NZ.H3P04 CllH14NZOl.H3P04
NAME
h-IP-IOOOBEhZEhESJLFOhVLl~YORUXYPRflLl~E h - lP-iOOJ8ENZEhESULFONYL IHYORflXVPRO~lhE
h-lP-1OCO8EhZEhESULFOhVLlHYORUXYPROLI~E h-IP-IOOO8E~ZihESJ~FO~VL~nYOROXYPROLl~E h - I P - I O D O B E ~ Z E ~ E S L L F O N YIGLUTAMIC A C 13 L h-lP-100OdEhZEhESULFO~YLlGLUTAMIC ACIJ h - l P - I O C O 8 E N L E h E S ~ L F O h Y L l G L u T A M I C ACID BENZOIC A C 1 0 ~ 4 - O H ~ 3 r 5 - 0 I - 1 0 D O l B U T Y L E S T E R 8ENZOIC bCID14-flHv 3 r 5-01-IOD01 S-BUTYL E S T E R BENZOIC A C I O ~ 4 - O H ~ 3 r 5 - D I - I O O O 1 D - O H - B U T Y L ESTER
306
306 12
306 306
306 306 306
12 24 24 24 12
A A
A A A
382
382 382 441 186 3 394 344 254
3.33
0.23 -0.16 0.53 1.00
=
8
8
8 8
338 2
69 338 4 254 338 3 40 82 218 304 304 304
12 12 44 44 44
0.91
1.01 -0.12 0.15 0.21
8
A A
0.51
-2.30 -1.40
-2.30
-0.52
1.53
-2.86 -2.80 -2.68 -1.04 -4.00
0.05 1.53
56
304 304 304 393
-1.04
-3.52
63
15 2 15 63 2 2 2 13 13 -3.42 0.13 0.14 -0.18 0.38 0.45 0.48 -0.69 0.32 -1.66 0.32 0.85 0.40 0.62 0.90 0.13 0.14 -0.05 0.09 0.15 0.18 0.07 0.16 0.46
56
113 343 113 393 343
= =
A 8
0 0
8
A
343
343 130 130 393 343 344 393 343 343 343 393 343 393 343 130 343 343 304 10 295 141 141 141 67 141 141 141 141 -61 67 431 141 141 141 141 141 141 338 338
-0.06
0.69 0.40 1.17 1.38 0.34 0.82 -0.05 -0.25 0.85 1.18 1.26 1.31 0.34 1.03 1.25 2.33
63
=
N N 8 A
A
2
44
63
2 2 2
0.67
-0.57 0.12 -2.52 0.85
63
2
=
N N A
A
0.63
0.71 -0.10 0.60 1.17 -0.70 3.27
63
2 13 2 2 52
2.33
0.30 3.82 3.10 3.61 -0.70 3.07 2.49 2.88 2.88 -2.78 -0.15 -0.66 1.71 2.49 2.54 2.57 1.49 1.57 1.17 -0.92 -1.52 1.15 1.01 0.64 0.94 0.07 -0.07 1.35 -1.48 -3.57 0.98 1.78 1.38 -0.32 1.60 1.38 -0.58 1.30 -0.69 -1.57
-0.08
-0.21 -0.43
330
393 56 343 393 415 343 343 343 415 416 138
44 44 44
0.77
TETRAHYORO-8-CARBOLINE ANT 1PY R I N ANT IPY R INE ANTIPYRINE ANTIPYRINE ANTIPYRINE ANTIPYRINE ANTIPYRINE ANTIPYRINE ANT I PYR I N ANTIPYRINE ANT IPY R I N ANTI PY R INE ANTIPYRINE ANT IPY RlNE HYOANTDINI~-ETHYL-~-PHENYL MALONAMIDE~2-HETHYLBENZAL MALONAMIOE,4-METHYLBENZAL MALONAMIOE~3-METHYL8ENZAL TRYPTOPHANt OL MALONAMIOEI~-NETHOXYBENZAL MALONAMIOEI~-METHOXYBENZAL MALONAM I D E t 3-METHOXYBENZAL SULFAMEKAZINE SULFAMERAZINE SULF AM ERA2 I NE SULFAMERAZINE SULFAMERAZINE SULFAMERAZINE SU LF AMERAZ I N E SULF AM ERA Z I NE SULFAMERAZINE SULFAMETHOXYPYRIOAZINE SULFAMETHOXYPYRIOAZINE SULFAMETHOXYPYRIOAZINE SULFAMETHOXYPYRIOAZINE SU LF AM ETHOXYPYR I OA Z I N E SULFAMETHOXYPYRIOAZINE SULFAMETHOXYPYRIDAZINE SULFAMETHOXYPYRIOAZINE SULFAMETHOXYPYRIOAZIhE SULFAMONOMETHOXIhE SULFAMCNOMETnOXINE SULFAMONOMETflOXI hE SU LF AMONDM E T hOX IhE SULFAMONDMETdOXINE SULFAYONOMETHOXIhE SJLFAMOhOMETHOX I N ClNhAMIC AC10,ETHYL ESTER 5-INOAhOXYACETIC ACID TRYPT3PHANE HYDROCHLORIDE STVRENEI~-I-PROPYLIB-NITRO S T YREhEt 4-M ETHYL 90-N I TRO, 8-ETnYL ST YREhEv 2-METHYL v B-NI TROIB-ETHYL L-PHENYLALAh INEI ACETYL STYRENE, 2-EThOXYv 8-NITROvB-METrlVL STYRENE,4-METHOXYIB-NITR0,8-ETnYL S T Y R E N E I ~-METHOXYI 8-N1 TROIB-ETHYL STYRENEI 3-YElkl0XY18-N I TRO. 0-ETHYL N-ACETYLTYROSINE/L/ N-ACETYLTVROSINE/L/ 8thZOYLTHREON I N E STYRENE~3.4-OIMETHOXYt 8-NITROIB-METHYL STYRENES 21 5 - O I M E T H O ~ Y t B - N I TR0.B-METHYL STYRENES 21 ~ - D ~ M E T H O X Y I B - ~ I T R O I B - M E T H Y L STYRENE. 2 9 3-OIMETHOXY t 0-hl TROIB-METHYL STYREYEv4-rlYDROXYs ~ - E T H O X V , ~ - N I T R O I B - M E T H Y L STYRENEI 4-HYOROXYv 3-ME ThOXYs 8-N I TR0. 8-E THYL 4-AMINOANTIPYRINE 4- AM INOANT 1PY R I N E
63
2 63
44 2
2 2
44 14
1.15 = 1.01 = 1.19 N 1.35 N 0.67 N 1.34 A 1.22 0.61 A
4-AMIhOANl IPYRIhE
SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE SULFISOXAZOLE P-AMINOSALICYLIC ACIOI~-CHLOROBUTYL E S T E R N-METHYLNORFENFLURAMI" N-IP-1OOOBENZENESULFONYL)VALINE N-IP-1OOOBENZENESULFONYL)VALXNE N-IP-IODO0ENZENESULFONVL)VALINE N- IP-IOOOBENZENESULFONYL )METHIONINE N-IP-XOOOBENZENESULFONYL~METHIONINE N- lP-IODOBENZENESULEOff1L )METHIONINE 5-METHYLTRY PTAMINE PHOSPHATE 5-METHOXYTRYPTAM I N E PHOSPHATE
306 ~.
306
2.41 1.57 2.41 1.35
A A A A
306
306 12 46 46
306
306 430 430
-0.69 -1.57
= =

NO. 4101 4102 4103 4104 41C5 41C6 4107 4108 4109 4110 4111 4112 4113 4114 4 1 15 4116 4 117 4 1 18 4 1 19 4 1 20 4121 4122 4123 4124 4125 4126 4127 4128 4129 4130 4131 4132 4133 4134 4135 4136 4137 4138 4139 4140 4141 4142 4143 4144 4145 4146 4 1 47 4148 4149 4150 4151 4152 4153 4154 4155 4156 4157 4158 4159 4160 4161 41t2 4163 4164 4165 4166 4167 4168 4169 4170 4171 4172 4173 4174 4115 4176 4177 4178 4179' 4180 4181 4182 41e3. 4184 4185 4186 4187 4188 4189 4190 '4191 4192 4193 4194 4195 4196 4197 4198 4199 4200 SOLVENT CYCLOHEXANE CHCL3 ACETATE I-PENT. CCL4 MIXEO SOLVYl OCTANOL OCTANOL QCTANOL OCTANOL OCTANOL OILS OILS OILS OILS OCTANOL OCTANOL OCTANOL OCTANOL OILS OCTANOL TOLUENE CHCL3 N-bEPTANE OLEYL ALCOHOL I-PENT. ACETATE I-PENT. ACETATE I-PENT. ACETATE I-PENT. ACETATE HEXANE HEXANE HEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL HEXANE N-HEPTANE OCTANOL HEXANE N-HEPTANE CHCL3 N-PEPTANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL PARAFFINS OCTANOL N-PEPTANE N-HEPTANE N-HEPTANE N-HEPTANE N-PEPTANE N-HEPTANE N-HEPTANE HEXANE N-kEPTANE SOZETHER+50%OHF SOIETHER+5O~DHF 500ETHER+501OMF OILS HEXANE CHCL3 N-HEPTANE DIETHYL ETbER CHCL3 4-HEPTANE N-HEPTANE CHCL3 N-HEPTANE OCTANOL N-HEPTANE XYLENE OCTANOL CHCL3 N-PEPTANE OCTANOL OCTANOL OCTANOL OCTANOL DCTANOL OCTANOL OCTANOL N-HEPTANE OCTANOL CHCL3 I-PENT. ACETA7E CCL4 CHCL3 OILS OILS BENZENE N-HEPTANE N-HEPTANE N-HEPTANE OCTANOL OILS 0 C1ANOL REF FOOT NOTE 141 399 399 399 LOGP SOLV 2.56 2.15 1.93 0.84 LOGP OCT 1.62 1.82 EMPIRICAL FORMULA NAME
1 1
433
428 22 6 255 255 255 362 385 417 361 56 10 10
0.88
-0.03 0.09 2.42 2.77 2.77 0.84 1.41 1.46 1.03 3.57 2.59 2.69 2.71 0.63 3.46 3.28
31 31 44
-0.03
0.09 2.42 2.77 2.77 1.98 2.47 2.52 2.19 3.51 2.59 2.69 2.71 1.76 3.46 4.45 1.73 3.31
= = = =
A A A A
10
345 437 150 396 396 390 418 418 418 418 39 1 39 1 391 38 4 38 4 384 384 255
= = = =
A
=
A
22 .8 03 .2
2.77 3.76 3.78 3.58
3 3 3 3
3.72
3.74 3.52 3.01
3.08
1.09 0.89 0.93 2.31 2.40 2.63 2.80 -0.36 1.48 1.17 1.52 -0.14 0.18 -2.00 2.69 2.92
= = 2.63 = 28 .0 = -0.36 =
2.31 2.40 1.52 -1.25 2.92 2.20 2.01 1.68 0.96 1.34
39 1
370 384 3 76 370 14 14 44
=
N
322
42 1 437 349 437 341 341 316 341 419 419 419 419 419 419 419 391 400 125 125 125 345 372 396 396 37 4 396
2.20
60
60 2.01 1.68 0.96 0.55 1.34 -0.92 -1.20 -1.07 -0.25 -0.28 -0.49 -0.49 0.12 -3.25
= = = = = =
14
08 .2
0.52 0.61 0.39 1.02 3.46 2.03
2.84 2.10
2.32
1.55 2.74 2.44 2.56 2.29 2.73 2.47 2.29 1.41
31
31
8 8
1.80
31
31 31 31 44 31 31
138
396 396 396 255 421 422
3.25 1.88 1.59 2.94 2.04 2.73
8
B
=
8
20 .3
1.81 2.29
302
396 39 6 397 437 437 65 65 341 341 400 218 399 399 399
=
8
1.91
-0.04 1.16 2.24
1.16 2.24
0.00
46 53 60 60 14
0.00
-3.38
3 38
442 398 338 25 4
-2.03 1.23 1.49 -2.48 2.98 2.51 1 1 3.00 1 1.58 44 22 .2 1.95 1.80 44 0.51 44
-3.38 -2.03
1.23 1.49 2.98 2.95 2.94 3.21 2.69 2.96 2.83
= = = =
A N A A
05 .2
44 0.19 0.52 2.24 0.46 2.07
338
340 218 345 399
22 .1
1.61
=
=
A
20 .7
CllH14N202 CllH14N203 CllH14N203 CllHl4N203 CllH14N203 CllH14N205 CllH14N404Sl CllH1401 CllH1402 CllH1402 CllH1402 CllH14OZ 1 C 1 H14O2 CllH1402 CllH1403 CllH1403 CllH1403 C 11H1403 CllH158RlN203 CllH15CLZ06PlSl CllHl5NlOl CllHl5NlOl CllH15N101 CllHl5N102 C 11H15N 1 0 2 CllH15N102 CllHl5NlOZ CllH15N102 C l l H I 5N102 CllH15N102 CllH15N102 CllH15Nl02 CllH15N102 CllHl5N102 CllH15N102 CllH15N102 C11 H15NlO2S1 CllH15N103 CllHl5N103 C 11H l 5 N 1 0 3 CllH15N104 C11 H15N505 CllHl6CLlNl CllH16CL104PlSl CllHl6N105Pl CllH16Nl06PlS1 CllH16N2 CllH16N2 CllH16NZ CllHl6N2 CllHl6NZOl CllHl6hZOl CllH16N201 CllH16N201 CllH16N201 CllH16N201 CllHlbNZOl CllH16N202 C11 H l bN202 C l l HlbN202S 1 CllH16N203 C11 H16N203 CllH16N203 CllHlbOl CllH17N1 C11H17N1 CllH17N1 CllH17N1 CllH17N1 C l l H17N1 C11H17N1 CllH17N1 CllH17N1 C11H17N1 C11H17Nl CllH17N101 CllHl7NlOl CllH17N101 Cl1 H17N501 C11 H1704 P1S 1 CllH17DbPlSl CllHl88RlNl CllH188RlNl CllHl8NZ CllH18NZ CllH18NZOZ.HBR CllHl8N202S1 C11 H 1 8 N 2 0 2 S l CllH18NZD2S1 CllH18N202S1 CllH18N20251 CllH18N202S1 CllHl8N202S1 CllH18N202Sl C11 H18N202S 1 CllH18N202Sl C l 1 H18N202S 1 CllH18N203 C11 H18N203 CllH18N203
ALLOBARBITALvN-METHYL T AL LOBAR8 I A L v N-METHYL N-ACETYL-A-HYOROXYMETHYL-8-OH-4-NITROPHENETHYL AMINE 6-METHYLTHIO-9-8-O-RI8OFURANOSYL-9-H-PURINE 1407741 2-PENTANONE, 5-PHENYL ESTER ACETIC ACIDIC-PHENYLPROPYL 4-PHENYLBUTYRIC ACIDIMETHYL ESTER A-PHENYLVAL ER I C AC I O 2-PHENYLVAL ER I C AC IO 4-PHENYLVALER I C A C I O 5-PHENYLVALER I C AC IO P-HYOROXYBENZOIC ACIO*BUTVL E S T E R PHENOXYACETIC ACID.3- ISOPROPYL PHENOXYACETIC ACIOe4-ISOPROPYL PHENOXYACETIC ACI0.3-PROPYL BARBITURIC A C I O I S - ~ U T Y L ~ ~ - B R O M O A L L Y L 09 0-01 1-0-1 21 6-CL2-4-MESULFONYLPHENYL) PHOSPHATE N-BUTYL-SALICYLIOENEIMINE I S C H I F F BASE) PHENMETRAZINE PHENMETRAZINE P-AMINOBENZO I C ACI DIBUTYL ESTER ESTER P-AMINOBENZOIC ACI0.1-BUTYL P-AMINOBENZOIC ACIDIN-BUTYL ESTER P-AMINOBENZOIC ACID, sEc-euTYL E S T E R P-AMINOBENZOIC ACIDIT-BUTYL ESTER N-METHYL C A R B A M A T E I ~ - I - P R O P Y L P H E N Y L N-METHYL C A R B A M A T E I ~ ~ ~ , ~ - T R I M E T H Y L P H E N Y L N-METHYL C A R B A M A T E I ~ ~ ~ ~ ~ - T R I M E T H Y L P H E N Y L N-METHYL-2-I-PROPYLPHENYLCARBAMATE N-METHYL-2-PROPYLPHENYLCAR8AMATE N-HE THY L-3- I-PROPY LPHENY LCAR BAMA TE N-METHVL-4-I-PROPYLPHENYLCAR8AMATE VALERIC ACIDI~-AHINO-~-PHENYL N-METHYL C A R B A M A T E ~ 3 r 5 - O I M E T H Y L 1 4 - n E T H Y L T H I O P H E N V L P-AMINOSALICYLIC ACIDIN-BUTYL ESTtR N-METHYL-2-I-PROPOXYPHENVLCARBAHATE N-METHYLCARBAMIC ACIOIO-I-PROPOXYPHENYL ESTER P-AMINOSALICYLIC ACIO~4-HYDROXYBUTYL E S T E R 1-METHVLGUANOSINE
G-IP-CHLOROPHENYLI-PROPYLOIHETHYLAMINE
O~O-OIET-O-l3-CL-4-METHYLTHlOPHENYL)PHOSPHATE PHOSPHONATEvO-IP-N ITROPHENYL I-0-PROPYL *ETHYL O~0-DIET-O-12-NITRO-4-METHIOPHENYLIPHOSPHATE 4-lN~N-DIHETHYLl-3-PYRIOYL8UTENE-l-YLAMINE METHYLANA8AS INE 4- IN-P IPERIOYL I - A N I L I N E
3-PYRIOYLETHYL-2-IN-PYRROLIDINEI
UREA, ETHYL-M-PHENETYL/UNSYH/ UREAIETHYL-O-PHENETYL/UNSYM/ UREA, ETHYL-P-PHENETYL/UNSYM/ UREA,N-BUTYLPHENYLUREA, N-PROPYL IH-TOLYLUREAIN-PKOPYLvO-TOLYLUREA, N-PROPYL. P-TOLYLN-METHYL CARBAHATEI 3 - M E T H Y L ~ 4 - D I H E T H Y L A H I N O P H E N Y L PILOCARPINE 5-ALLYL-5-I-BUTYL-2-THIO8ARBITURIC ACIO/8UTHALITAL/ 5-ALLYL-5-8UTYL8ARBITURIC ACID 5-ALLYL-5-I-PR-l-METHYLBAR81TURIC ACID BAR8ITURIC ACIOIALLYLIS-BUTYL PENTANOL. 5-PHENYL DIMETHYLAMPHETAM INE OIHETHYLAMPHETAHINE N- THY L-G-PHENYL PROPYL AM INE ETHYL AMPHETAMINE ET HYLAHPHETAMINE ET HY L AHPHET AH I NE HEPHENTERHINE HEPtiENTERHINE G-PHEhYLPROPYLDIMETHYLAMINE G-PHENYLPROPYLOIMETHYLAM N IE PROPYL AMINE~N-ME,N-Il-BENZYLl P-DIETHYLAMINOBENZYL ALCOHOL METHYL EPHEDRINE METHYL EPHEOR I N E AOENINEs9-( 1-HYOROXYMETHYL-PENTYL) 0.0-DIETHYL-0-14-HETHYLTH1OPHENYL)PHOSPHATE O~O-OIETHYL-O-~4-HETHYLSULFONYLPHENYLlPHOSPHATE BENZYL 0 1 METHYL ETHYL ARHON I U H BROMIDE HEXVLPYRIDINIUH BROMIDE Ne N-01 ETHYL-3-PYRIOYLETHYLAMINE 4-IN~N-OIMETHYLl-3-PYRIDYL8UTYLAHINE SP IRO-(N'-METHYLP IPERIDYLz4' I-N-ETSUCCINIMIDE BARBITURIC AC 101 5-ETHYL-5- I-ARYL-2-THIO BARBITURIC AC 1015-ETHYL-5- I-AMYL-2-THI 0 BARBITURIC A C I D I ~ - E T H Y L - ~ - I - A M Y L - ~ - T H I O BARBITURIC AC 1015-E THYL-5- I-AMYL-2-TH IO BARBITURIC A C I O ~ E T ~ l - M E 8 U ~ Z - T H I O / T H I O P E N T A L / BAR8ITURIC ACIOt E T , l - M E B U ~ 2 - T r l I O / T H I O P E N T A L / BAR8ITURIC ACIOIETI ~ - H E ~ U I Z - T H I O / T H I O P E N T A L / BARBITURIC A C I D ~ E T ~ 1 - H E 8 U ~ 2 - T H I O / T H I O P E N T A L / 8ARBITURIC ACIOv ET-l-MEBU, 2-THIO/THIOPENTAL/ BARBITURIC A C I O ~ E T ~ l - M E 8 U ~ Z - T H I O / T H f O P E N T A L / BAR8 ITUR I C A C I O ~ E T ~ 1 - M E 8 U ~ 2 - T H I O / T H l O P E N T A L / BARB I TUR I C ACID, 5-AHYLC5-ETHYL BARBITURIC ACID, 5-AMVL-5-ETHYL BARBITURIC A t 1 Ot 5-ETHYL-5- I-AHYL/AHOBARB I TAL/

REF FOOT NOTE
399 345 399 399 399 399 399 345 398 399 399 399 340 125 218 LOGP SOLV 1.73 0.46 0.72 2.13 0.34 LOGP OCT 2.24 1.61 2.10 2.03 2.22 2.03 1.90 1.77 1.88 1.90 1.93 1-80 2.12 0.35 0.89 N A A EMPIRICAL FORMULA CllH18N203 C l l HlBN203 CllH18N203 CllH18N203 C l l H18N203 CllHlBN203 C l l H I 8N203 CllH18N203 CllH18N203 CllHl8N203 C11 H l BN203 CllHlBN203 C l 1H l 8 N 2 0 3 CllHlBk203 C 11H18k2D4 Cllh19N102 CllH2OIlNlO2 CllH2OIlNlO2 CllH20I lNlO2 CllH21N505 CllH2ZIlN102 CllH22IlNlO2 CllH22N203 CllH22N2Sl CllH24I lN1 C l l H 2 4 1I N 1 C11 H24N202 CllH24N202 CllH24N202 CllH24N202 C 11H2402 S N l CllH2611Nl CllH2611Nl C 11H26S I 1 C12HbF2N2 C12H7CL 1N2 C12H7CL2NlSl C12H7CL2NlSI C12H7F 1N2 C12H7N302 Cl2H8 B R lN l S 1 C12H8CLlNlS1 C12H8CL6 C12HBCL601 ClZHBFlNlSl C12HBIlNlSl Cl2H8N2 C12 H8N2 H20 C12H8N2 C12 H8 N2 0 2 Cl2HBN202 C12 H 8 O l C12H803 C 12 H8 0 4 C12H9CL2N102 C 12H 9 N l C1 2 H9 N 10 1s 1 C12 H9N103 C12H9N103 C12 H 9 N l S 1 C1 2 H 9 N l S 1 C12 H9NA 1 0 1 C12H9NA101 C12H10 C12HlO Cl2HlO C12HlOCLlN102 C 12 HlOC L 1N 1 0 2 C12HlOCLlN102 Cl2HlOCLlN102 C12HlOCL202 C12HlOFlN102 Cl2HlON2 C12H10N2 C12HlON201 C12HlON201 Cl2HlONZOl Cl2HlON202 C12HlON202 NAME
NO. 4201 4202 4203 4204 4205 4206 4207 4208 4209 42 1 0 4211 42 1 2 4213 4214 4215 4216 42 17 4218 42 19 4220 4221 4222 4223 4224 4225 4226 4227 4228 4229 4230 4231 4232 4233 4234 4235 4236 4237 4238 4239 4240 4241 4242 4243 4244 4245 4246 4247 4248 4249 4250 4251 4252 4253 4254 4255 4256 4251 4258 4255 4260 426 1 4262 4263 4264 4265 4266 4267 4268 4269 4 2 TO 4271 4272 4273 4274 4215 4276 4277 4278 4279 42 80 4281 4282 4283 4284 4285 4286 4287 4288 4289 4290 4291 4292 4293 4294 4295 4296 4297 4298 4299 4300
SOL V EN1 CHCL3 OILS BENZENE I-PENT. ACETATE CCL4 OCTANOL CHCL3 OILS OILS BEN 2 EN I-PENT. ACETATE CCL4 N-HEPTANE 500ETHERt50ZOMF OCTANOL OCTANOL CHCL3 CHCL3 CHCL3 SEC-BUTANOL CHCL3 CHCL3 DIETHYL TI-ER PARAFFINS CHCL3 C HCL 3 DIETHYL ETkER 0 1 ETHYL ETCER DIETHYL E T k E R 0 1 ETHYL ETkER OCTANOL OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE N-HEPTANE N-PEPTANE CYCLOHEXANE CYCLOHEXANE N-HEPTANE N-HEPTANE HEXANE HEXANE N-PEPTANE N-I-EPTANE CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OC TPNOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL N- P, T AN E EP OCTANOL CYCLOHEXANE OCTANOL N-PEPTANE OCTANOL OCTANOL OCTANOL OCTPNOL OCTANOL CYCLOHEXbNE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL OCTPNOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OC TANOL OC TPNOL CHCL3 CYCLOHEXANE CHCL3
1 1 1 1 1
44 1
20 .3
1.38 0.64 0.76 0.51
=
N A A A
1
1
2.03
-0.03 -1.30 0.53 0.35 0.89 -3.20 -3.71 -3.09 -1.31 -3.28 -3.09 -1.06 1.08 -2.70 -2.52 -0.12 -1.02 -0.73 -1.07 1.68 -1.07 -2.19 4.24 1.96 1.96 0.81 0.83 1.80 1-01 3.60 3.32 5.00 4.56 3.61 3.95 1.81 1.83 2.84 1.02 1.35 4.12 0.67 1.12 3.60 3.29 -1.09 1.29 0.13 4.15 3.88 0.41 0.22 4.09 3.16 4.04 2.91 3.54 3.55 1.24 2.18 2.75 3.82 2.55 2.23 2.55 2.10 1.05 2.02 1.08 -1.30 1.74 1.91 4.21 4.36 1.94 C.98 2.49 2.70 2.40 2.53 2.14 2.31 0.45 1.09 3.41 4.45 2.16 1.82 1.97
348
424 424 424 84 424 424 378 241 424 424 378 378 378 378 235 297 297 298 304 304 443 443 304 304 443 443 317 317 443 443 141 283 218 30 4 304 218 141 141 304 309 443 141 141 46 46 46 19 46 46 44 46 46 44 44 44 44 46 46
= =
-2.34 -0.01
0.83
0.04
0.30 00 .0
1.68 -1.07 -2.19 4.24
e e
= =
= =
1.83 2.84 4.12
= = =
BARBITURIC A t 1015-ETHYL- 5-I-AMYL /AMOBARB I TAL/ BARBITURIC ACID, 5 - E T H Y L - 5 - I - A M Y L / A M O 8 A R B I T A L / BARB ITUR IC AC 10s +ETHYL- 5- I-AMYL/AMOBARB I TAL/ I TAL/ BAR8 I T U R I C ACI 014 - E T H Y L - 5 - I - A M Y L / A M O B A R B BARBITURIC A C I D ~ 5 - E T H Y L - 5 - 1 - A M Y L / A M O B A R 8 I T A L / BARBITURIC ACIDS 5-ET-5-( l-MEBUI/PENTO8ARBI TAL BARBITURIC ACID, 5-ET-5-1 l-MEBU)/PENTOBARBI TAL/ BARBITURIC ACIOt 5-1-5-1 1-MEBU) /PENTOBARB1 TAL/ BARBITURIC ACID, 5-1-5-1 1-ME BUl/PENTOBARBITAL/ BARBITURIC A t IO. 5- 1-5-1 1-MEBU I /PE NTOBARBI TAL/ BARB I T U R I C ACI 01 5-ET-5-1 1-MEBU I /PENTOBARB1 TAL/ BARBITURIC ACID, 5-ET-5-( l-MEBUl/PENTOBARBI TAL/ BARBITURIC A C I 0 ~ 5 - E T - 5 - 1 1 - M E 8 U I / P E N T O B A R 8 I T A L / BARBITURIC ACID.5-ET-5-1 l-MEBUI/PENTOBARBI T A L I BARBITURIC ACIDv 5-ETHYL-5130H-l-METHYL8UTYLI N-HEXANOYLCYCLOBUTANECARBOXAMIOE N-METHYL-I-PUINUCLIDINOL-3-ACETATE METHIOOIOE TROPINYL A C E T A T E - M E T H I O D I O E / T R A N S / TROPINYL ACETATE-METHIOOIOE/CIS/ ARGINYLGLUTAMIC ACID ~ ~ Z I ~ - T R I M E T H Y L - ~ - A C E T Y LP I P E R I O I N E METHIODIOE 11315-TRIMETHYL-4-ACETYL P I P E R I O I N E METHIODIOE MORPHOLINOFORMIC ACID.DIETAMINOETHYL ESTER N-OCTYLETHYL ENETHIOUREA 112r2r6r6-PENTAMETHYLPIPERIOINE METHIODIOE 1 r 3 1 3 1 5 5-PENTAMETHYLPIPERIOINE METHIOOIDE ~ N-BUTYLCARBAMIC ACIOIOIETAMINOETHYL E S T E R N-T-BUTYLCARBAMIC ACIOIOIETAMINOETHYL ESTER NvN-OIETHYLCARBAMIC ACID~OIETAMINOETHYL ESTER N-SEC-BUTYLCARBAMlC ACIDIOIETAMINOETHYL ESTER TRIPROPYLTIN ACETATE TR IMETHYL-OCTYL-AMMON IUM IODIOE TRIPROPYL-ETHYL-AMMONIUM IODIOE SILANE, OCTYL-TRIMETHYL HALONON I TRILE. 2,6-0IFLUOROCINNAHAL MALONOhITRILE~2-CliLORUCIhkAMAL PnEkOTPlAZIiE,21 7-DICHLORO Prl E h O T P I A Z I N E I 3 1 7-OICHLORO MALOkUhI TRICE. 2-FL JJAJCIhhAMAL MALONONITRILEI 2-NITROC INNAMAL PHENOTHIA Z I N , +BROMO PH EN01 H I A2 I NE, 3-CHLORO ALDRIN DI EL DR I N PHENOT PI A Z INE 9 3-F LUORO PHENOT H I AL INEI 3- 1000 MALONONITRILE, CINNAMAL 0-PHENANTHROL I N HYDRATE PHENAZ I N E MALONONI 1 R I L E, 4-METHOXYCARBONYLBENZAL HALONONITRILEI~-METHOXYCAR~ONYLBENZAL OIEENZOFURAN 114-NAPHTHOPUINONEv 2-ACETYL
~~~-NAPHTHOUUINONEI~-METHOXYCARBONYL ETHYLCYANOACETATEIZ~~-DICHLOROBENZAL
3.29 1.29 4.15 0.41 0.22 4.09 3.16 4.04
= =
= = =
56
443 283 283 56 309 428 304 304 304 141 304 304 10 304 304 304 304 141 141 304 141 304 444 56 276 445 133 141 141 186 10 141 141 304 141 2 76 235 444 304 444 74
= =
3.82
CARBAZOLE PH EN07 H I A 2 1NE, 3-HY DROXY le4-NAPHTHOQUINONE, 2-ACETAMIDO 1 9 4-NA PHTHOPUINONE. 2- ACE T A M ID0 PHENOT H I A2 I N PHENOTkIALINE SODIUM P-PHENYLPHENOXIOE IPKA=9.511 SODIUM P-PHENYLPHENOXIOE IPKA=9.51;PH=12.71 81 PHENYL BIPHENYL D l PHENYL ET HYLCY ANOACETATE, 2-CHLOROBENZAL ET HYLCY ANOACETAT E, 3-CHLOROBENZAL ETHYLCYANOACETATEI 4-CHLOROBENZAL 1 ~-NAPHTHOPUINONEI 2-CHLOR0,3-0 I M THYLAMI NO , E ACETYLACETONE, 2r6-OICHLORO-BENZAL ETnYLCYANOACETAlE~ 3-FLJROBEhZAL AZOBiIvZENE MA,JhOhlTRILE. 2-ETnYLBEhZAL MALONON I T R I L E. 4-ETtiOXYBENZAL MA L O N 0 N I T R I L E t 3- ETHOXY8 EN2 AL MALOhDNlTRlLE* 2-ETHOXYBENZAL MAL)\:*. I T & I L E , 314-31ME TnOXYBEdZAL MALO\O%ITRILEI Z14-OlHETHOIYEE%LAL HALJhUN IT4 I L E I 3 , G - O I M i T H O X Y B E i L AL
~ ~ ~ - ~ A P H T ~ O P U ~ ~ O ~ E I ~ - A H I ~ O ~ ~ - A C E T A ~ I ~ O
30
2.38 4.21 4.36
=
=
Cl2HlODl Cl2HlOOl C12H1001 C12H1002 C12H1002 C12H1002S1 C12H1003 Cl2H1003 C12H1003 C12H1004 C12H1004 ClZHlOSl ClZHlOSl Cl2HllBRlN202Sl C12HllER102 C l 2 H l 1CLlN202S1
26
2.40 2.53
26
ET nYLCYAkOACETAT E, 3-h I TROBEhZAL h l - 1 3 9 5 - D l h I T R O P n E ~ I LI SLLFAhlLAHIOE OIPnElvYL E T n f R OIPHEhYLETnER C-PHEW I L DrlEluOL P-PtiElvYLPHEhOL 1, *-hAktilHOCJIk;kE. 6.7-OIMETtiYL l r 4-NAPHTHOQU1NONE~2~3-DIMElHYL SULFOYEIOIPHENYL A C E T I C ACIO.2-NAPHTHYLOXY 1I 4-NAPHTHOOU INONE t 2-METHYL-3-HETHOXY
lr4-NAPHTHOPUINDNE~2-METHYL~3-METHOXY
30
3.47 4.45 2.62 2.44
= =
N
COUMARIN-3-CARBOXYLIC AClOlETHYL ESTER 11 4-NAPHTHOOUINONE, 2 r 3-OIMETHOXY DIPHENYLSULF IOE DIPHENYCSULFIOE
N1-13-BROMOPHENYLlSULFANlLAMlOE
ACETYL A C ETONE 4-BROMO- EENZ AL N l - I 3-CHLOROPHENYL ISULFAN ILAHIOE
30

LOGP OCT EMPIRICAL FORMULA ClZHllCLlOZ C12HllCL102 C12HllCL102 ClZHllFlOZ C12HllIlNZOZS1 Cl2HllNl ClZHllNl ClZHllNl ClZHllNl ClZHllNl ClZHllNl C12rlllN102 C l ZHI 1h l O 2 C l Z H l l k 102 C12rlllh102 C l Z k l I N 102 C12HllN102Sl C12HllN102Sl C12HllN102Sl C12H11N3 C12HllN304Sl C12HllN304Sl C l Z H I 1N7 C12H128RlNl ClZH12N202Sl C12H12N203 ClZH12NZ03 C12H12N203 C12HlZN203 ClZHlZNZ03 C12H12NZ03 C12HlZN203 ClZH12N203 C 12 H12N203 C12H12N203 C12H12N203 NAME ACETYLACETONEv 4-CHLORO-BENZAL ACETYLACETONE. 3-CHLORO-BENZAL ACETYLACETONEt 2-CHLORO-BENZAL ACETYLACETONE. 4-FLUJRO-BENZAL
NO. 4301 4302 4303 4304 4305 4306 4307 4308 4309 4 3 10 4311 4 3 12 4 3 13 4314 4315 43 16 4317 4318 4 3 19 4320 4321 4322 4323 4324 4325 4326 4327 4328 4329 4330 4331 4332 4333 4 3 34 4335 4336 4337 4338 4339 4340 4341 4342 4343 4344 4345 4346 4347 4348 4349 4350 4351 4352 4353 43s4 4355 4356 4357 4358 4359 4360 4361 43t2 4363 4364 4305 4366 4367 4368 4369 4370 4371 4372 4313 4374 4315 4316 4317 4318 4379 4380 4381 4382 4383 4304 43e5 4386 4387 4388 4389 4390 4391 4392 4393 4394 4395 4396 4397 4398 4399 4400.
SOLVENT CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CHCL3 PARPFFINS PARAFFINS PARAFFINS OCTANOL OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE HEXANE OCTANOL OCTANOL 0 1 ETHYL ETHER CHCL3 HEXANE BENZENE CHCL3 CHCL3 OCTANOL OCTANOL CHCL3 OCTANOL CHCL3 OILS OILS OILS BENZENE I-PENT. ACETATE CCL4 OLEYL ALCOHOL SOXETHER+5OXOMF CYCLOHEXANE CYCLOHEXANE DIETHYL ETkER N-CEPTANE N-hEPTANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OILS OILS OILS N-HEPTANE 501ETHER+50XOMF CYCLOHEXANE MIXED S O L V I 1 OCTANOL D I ETHYL E T k E R CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 OCTANOL 0 1 ETHYL ETkER CHCL3 CHCL3 CHCL3 CHCL3 BENZENE I -BUTANOL I-PENT. ACETATE CCL4 N-kEPTANE OCTANOL CHCL3 CHCL3 BENZENE I-BUTANOL I-PENT. ACETATE CCL4 OCTANOL OCTANOL CHCL3 OC T ANOL OCTANOL OCTPNOL HEXANE CYCLOHEXANE HEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OC 1 ANOL MIXED S O L Y I 1 0 I LS
REF FOOT NOTE 304 304 304 304 444 316 316 316 276 309 235 141 30 4 391 3 84 3 a4 113 113 376 72 444 444 218 65 444
LOGP SOLV 1.67 1.69 1.99 0.95 2.47 2.10 1.67 1.74 3.34 3.22 3.50
30
2-71 N
Nl-l3-lOOOPHENYLISULFANILAMIDE
Z-AMINOBI PHENYL 3-AMINOBIPHENYL 4 - W INOB I PHENYL 01 PHENYL AM I N E 0 1 PHENYL AM I NE 0 1 PHENYL AM I NE BENZALCYANOACETIC ACIOIETHYL ESTER BENZALCYANOACETIC ACIOIETHYL ESTER N-METHYL CARBAMATETl-NAPHTHYL N-METHYL-A-NAPHTHYLCARBAMATE N-METHYL-8-NAPHTHYLCARBAMATE BENZENESULFANILAMIDE BENZENESULFANILAMIDE N-ME-N-ACETYLCARBAMIC ACID.4-BENZOTHIENYL ESTER P-AMINOAZOBENZENE N1-(3-NITROPHENYLlSULFANILAMIOE Nl-(4-NITROPHENYLISULFANILAMIOE PT ERIOINEt 2.49 7-TR I A M INO-6-PHENYL M DE BENZYL PY R I D I N I U BROM I N1-PHENYLSULFANILAMIOE BARBITURIC A C I D I ~ - E T H Y L - ~ - P H E N Y L / P H E N O B A R B I T A L / BARBITURIC A C I O I ~ - E T H Y L - ~ - P H E N Y L / P H E N O B A R B I T A L / 8ARBITURIC A C I D I ~ - E T H Y L - ~ - P H E N Y L / P H E N O B A R B I T A L / BARBITURIC A C I U ~ 5 - E T H Y L - 5 - P H E N Y L / P H E N O B A R B I T A L / BARBITURIC ACID95 ETHYL-5-PHENYL/PHENOBARBITAL/ BARBITURIC A C I O I ~ - E T H Y L - ~ - P H E N Y L / P H E N O B A R ~ I T A L / BARBITURIC A C I O I ~ - E T H Y L - ~ - P H E N Y L / P H E N O B A R B I T A L / BARBITURIC A C I O V ~ - E T H Y L - ~ - P H E N Y L / P H E N O B A R B I T A L / BARBITURIC A C I O I ~ E T H Y L - ~ - P H E N Y L / P H E N O B A R B I T A L / BARBITURIC A C I O + 5 - E T H Y L - 5 - P H E N Y L / P H E N O B A R B I T A L / CY ANOACETAMIOEI 3.4-OIMETHOXYBENZAL ACETYL ACETONEv BENZAL AOIPIC ACID-A-KETO-G-PHENYL 8-CHLORO-9-METHYLTETRAHYORO-B-CARBOLINE 6-FLUORO-9-HETHYLTETRAHYDRO-B-CAR8OLINE BENZIMIOAZOLE~5-BUTYL-2-lTRIFLUOROMETHYLl N-CYCLOPROPYLCINNAMAMIOE 1- CY CLOH EX EN E t 4-N 1TRO v 5-PHENYL VITAVAX ISOCARBOXAZIOE N-PROPYLPUINOLINIUM BROMIDE
3.34 3.22
= =
=
3.50
26 .3
2.59 0.42 2.36 2.56 2.62 2.87 1.96 3.50 2.44 1.52 0.98 -2.62 1.45 1.42 0.65 0.23 0.13 0.00 1.54 2.36 2.56 2.41 3.29 2.95
= =
A N
0 N N
30
30
46 30
2.88
2.02 0.98 -2.62 1.96 1.42 1.20 1.43 1.37 1.19 1.40 1.42 1.31 1.34 0.62
0.87 4.27 2.14 1.49 -2.52 1.22 6.20 3.70
= =
N
ao
=
N A A A A
A
399 82 345 398 399 399 399 82 125 304 304 414 441 441 206 446 141 235 283 65 447
1
44
1 -0.01
1
12
1 -0.63
0.78
-0.07 -1.63 0.96 0.87 -2.13
-2.30
4.27 -0.62
36 .0
65 46 24 24 2.14 1.49 -2.52 -0.03 5.51 2.76 -1.99 0.13 -2.81 -2.70 0.21 -0.06 0.73 0.66 -0.43 0.56 -1.35 -0.30 -1.06 -0.55 -0.69 -0.35
=
=
A A A
A-BROMO-I-VALERYL-SALICYLAMIDE
BENZOIC A C I D ~ 4 - O H ~ 3 ~ 5 - D I - I O O O ~ A M Y ESTER L BENZOIC AC 101 4-OH1 3 1 5-01- IOOOt E-OH-AMYL ESTER 9-METHYLTETRAHYURO-5-CARBOLINE 5-FURFURYL-5-I-PROPYLBAREITURIC ACIO/OORMOVIT/ MALONAMIOEIZI~-DIMETHOXY~ENZAL BARBITURIC ACIOI l-CARBOXYMETHYL-5r 5-OIALLYL SULFAMETHAZINE SULFAMETHAZINE SULFAMETHAZINE SULFAMETHAZINE SULFAMETHAZINE SULFAMETHAZINE SULF AMETHAZ INE SULF ISCMIOINE SULF I S O M I DINE SULF I S OM I O 1NE SULFISOMIOINE SULFISOMIOINE SU LF ISOM I DINE SULFISDMIOINE SU LF I S O M I I N E D SU LF ISOM 1 0 I N E SULF I O M I O I S NE SULF ISOMI DINE SULFAOIMETHOXINE SULFAOIMETHOXINE SULFAOIMETHOXINE SULFAOIMETHOXINE SULFAOIMETHOXINE SULFAOIMETHOXINE SULFADIMETHOXINE 3~PHENYLAMINO~4~AMINO~~~I~PR~llZ14~TRIAZINE-5-ONE 2 - I 5 ~ 6 i l r 8 - T E T R A H Y O R O N A P H T H Y L O X Y - ~ A C E T I C ACID AOIPIC ACIDIB-PHENYL GLUCOPYRANOSIOEI~-CHLOROPHENYL IBETA) G L U C O P Y R A N O S I O E ~ 2 - I O O O P H E N Y L (BETA) GLUCOPYRANOSIOEI~-1000PHENYL (BETA) N-MECARBAMIC ACID* 5 ~ 6 ~ 7 ~ 8 - T E T R I H Y D R O - l - N A P H T H Y L ESTER STYRENE.4-I-PROPYL.B-NITRO.B-METHYL N-METHYL C A R B A M A T E * N - A C E T Y L V ~ - U E - ~ ~ M E T H Y L T H I O P H E N Y L STYRENE13r4-DIMETHOXYIB-NITROIB-ETHYL STYRENE, ~ ~ ~ - O I M E T H O X Y I B - N I T R O I B - E T H V L STYRENE, 2 , 5-DIMETHOXY. 8-NI TRO.8-ETHYL STYRENEIZ~~-OIMETHOXYIB-NITROIB-ETHYL STYREN E l 4-HYDROXY v 3-ETHOXY r 8-NI TRO r B-E THYL G A L A C T O P Y R A N O S I O E I ~ - N I T R O P H E N Y L (BETA) G L U C O P Y R A N O S I O E I ~ - N I T R O P H E N Y L (ALPHA1 GLUCOPYRANOSI D E t 2-NITROPHENYL ( BETA) GLUCOPYRANOSIOEt 3-NITROPHENYL ( BETA) GLUCOPYRANOSIOE~4-NITROPHENYL (BETA) MANNOPYRANOSIOEI~-NITROPHENYLIALPHA) BARBITURIC A C I D ~ l - C A R B A M Y L M E T H Y L - 5 1 5 - D I A L L Y L A-BROMO-I-VALERYL-0-AN I S I O I N E
382
382
441 125 304 433 56 113 343 113 343 343 343 393 113 343
15 2 15
2 2
2 63 15
2
15
113 393 415 343 130 343 343 415 393 343 393 343 130 343 343 134 10 194 438 438 4 38 316 141 391 141 141 141 141 141
63
44 2 13 2
-0.52
-1.21 1.74 -0.40 -1.89 -3.85 1.56 1.49 1.31 0.70 2.48 1.89 -0.63 1.73 2.67 -0.60 0.26 0.27 0.75 0.92 3.52
2
44 63
2
63
2
13 2
2.20
2.17 2-66 2.68
3.22
2.24 -0.59 -0.39 -0.78 -0.51 -0.44 -0.18
438
438 438 438 438 438 433 447
-0.82
-0.02
C12H14 I 2 0 4 C12H14NZ 1.12 ClZH14N204 C12H14N204 C 12 H14N205 0.27 = C12H14N402Sl 0.08 A ClZH14NCOZSl 0.39 8 C12H14N4OZS1 0.33 B ClZH14N402S1 0 0 8 C12H14N402SI .3 C12H14N402Sl 0.40 0.72 A ' C12H14N402SI -0.30 = C12H14N402S1 0.71 8 C12H14N402S1 0.09 N C l Z H l 4 N 4 0 2 S l -0.04 N ClZHl4N4OZSl -0.33 N C 1 2 H l Q N 4 0 2 S I 0.12 N C12 H14N402S 1 0.18 A C12H14N402S1 1.94 C l Z H14N402S 1 -0.59 ClZH14N402Sl 0.25 A C 1 2 H14N402S 1 Cl2H14N402SI 1.56 = C l Z H 1 4 N 4 0 4 5 1 2.01 N C l Z H 1 4 N 4 0 4 S l 1.31 B C l Z H 1 4 N 4 0 4 S I 2.08 A C l Z H 1 4 N 4 0 4 5 1 2.93 C 12H14N404S 1 1.78 C12H14N404S 1 1.31 A C l Z H 1 4 N 4 0 4 S l 1.73 * C12H14N501 2.67 = C l Z H 1 4 0 3 0.67 A C12H1404 0.26 = ClZH15CL106 0.21 = C12H151106 0.75 = C l Z H 1 5 1 1 0 6 ClZH15N102 C12H15N102 ClZH15N102Sl ClZH15N104 ClZHEN104 C 1 2 H I 5 N1 0 4 C12H15N104 ClZH15N104 -0.59 = C12H15N108 4 - 3 9 C12H15N108 = C12H15N108 -0.78 -0.51 = ClZH15N108 -0.44 ClZH15N108 -0.18 = C12H15N108 C 12 H15N304 1.23 A C12H16BRlN102
NO. 4401 4402 4403 4404 4405 4406 4407 4408 4409 4410 4411 4 4 12 4413 44 14 4415 44 16 4417 4418 44 19 4420 4421 4422 4423 4424 4425 4426 4427 4428 4429 4430 4431 4432 4433 44 34 4435 4436 4 4 37 4 4 38 4439 4440 4441 4442 4443 4444 4445 4446 4447 4448 4449 4450 4451 4452 4453 4454 4455 4456 4457 4458 4459 4460 4461 44t2 4463 4464 4465 4466 4467 4468 4469 4470 4471 4472 447 3 4414 4475 4476 4477 4 4 78 4479 4480 448 I 4482 4483 4414 4485 4486 4487 4488 4489 4490 4491 4452 4493 4494 4495 4456 4457 4498 4499 .. 4500
SOLVENT N-HEPTANE CHCL3 N-HEPTANE N-HEPTANE CCL4 CCL4 OCTANOL CHCL3 CHCL3 OCTANOL 50LETHER+50XDMF OCTANOL CHCL3 I-PENT. ACETATE CCL4 5DZETHER+50XDMF SEC-BUTANOL OILS OCTANOL OCTANOL OCTANOL OCTANOL 01 ETHYL ETkER OCTANOL I-BUTANOL 501ETHER+50XOMF CHCL3 N-kEPTANE I-PENT. ACETATE OLEYL ALCOkOL HEXANE HEXANE HEXANE HEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTPNOL OCTANOL OCTANOL OLEYL ALCOHOL N-PEPTANE OCTANOL N-HEPTANE OCTANOL OCTANOL OCTANOL N-HEPTANE N-HEPTANE N-HEPTANE OCTANOL OILS XYLENE 01-BUTYL ETHER CHCL3 I-PENT. ACETATE CCL4 OCTANOL OLEYL ALCOHCL CHCL3 I-PENT. ACETATE CCL4 501ETHER+50%0MF PRIM. PENTANOLS CHCL3 N-HEPTANE DIETHYL ETkER CHCL3 N-HEPTANE N-I-EPTANE CHCL3 N-hEPTANE OCTANOL OCTANOL OCTANOL OC IANOL OCTANOL OC IANDL CHCL3 OILS CHCL3 I-PENT. ACETATE CCL4 DIETHYL Eli-ER OILS PRIM. PENTANOLS OCTANOL I -@UTAN O L I e U T ANOL OCTANOL DIETHYL ETkER 0 C T ANOL N-PEPTANE SEC-BUTANOL OCTANOL N-BUTANOL OCTANOL DIETHYL ETkER
REF FOOT NOTE 416 396 138 396 306 306 341 448 448 218 125 218 399 399 399 125 84 361 10 10 10 438
LffiP SOLV 1.12 3.22 2.74 2.83
L06P OCT. 2.53 2.02 1.92 1.49
EMPIRICAL FORMULA
NAME P-UIINOSALICYL I C ACID. 5-CHLOROAHVL E S T E R FENFLURAMINE FE NFLU RAM I NE FENFLURAMINE N-(P-IOOOBENZENESULFONYL )-[-LEUCINE N-1P-IODOBENZENESULFONYLILEUCINE
14 31
31 60 65 65
B
A A
0.20
0.09 1.49 -1.22 0.74 1.20 0.15 1.49 2.11 1 1.86 1 1 08 .8 12 0.46 1 9 -2.05 1.25 3.18 3.12 2.96 -0.71 -3.13 -1.35 -0.55 0.46 3.38 31 0.95 31 4.41 3 3.24 44 1.79 1.56 1.54 1.48 2.78 2.65 3.11 3.10 2.84 2.93 3.20 3.06 1.47 14 1.32 2.96 0.28 14 -2.67
1.20 1.17 1.49 1.58 1.75 1.95 -3.38 2.40 3.18 3.12 2.96 -0.71 -2.62 -1.35 -1.28 1.95 2.66 4.40 3.78
=
=
8
= = =
A
C12 H l 6 C L 1N 1 0 3 ClZH16F3Nl CIZH16F3Nl C12H16F3Nl t12H1611NlD4Sl ClZH1611N104Sl C12H16N2 ClZH16N202 C12H16N202 ClZH16N203 C12HlbN203 C12H16N203 C12H16N203 C12H16N203 C12Hl6N203 C12H16N203 C12H16N603 C12H1602 C12H16D3 ClZH1603 C12H1603
3-PYRIOYLMETHYL-N-PIPERIDINE
N t PI-OIMETHVLTRYPTAMINE t 5-HYDROXY N t WDIMETHYLTRYPTAMINE. 4-HYDROXY CYCLOBARBITAL CY CLOBARBITAL HEXOBARBITAL HEXOBARBITAL HEXOBARBITAL HEXOBARBITAL HEXOBARBITAL HISTIOYLHISTIOINE 6-PHENYLCAPROIC ACID PHENOXYACETIC ACIOI~-BUTYL PHENOXYACETIC ACIDI~-S-BUTYL PHENOXVACETIC ACIDv3-T-BUTYL GLUCOPVRANOSI OEi PHENYL 1 BETA) B-D-GLUCOPVRANOSIOE~P-HYOROXYPHENYL/AR8UTIN/ 81 O-GLUCOPYRANOSIOE~P-HYOROXYPHENYL/ARBUT1N/ B.0-GLUCOPYRANOSIOEIP-HYOROXVPHENYL/ARBUTIN/ 5-(2-8ROMALLYL )-5-(l-METHYLBUTYL I-BAR81 TURIC ACID PHENDIMETRAZINE PHENDIMETRAZINE P-AMINOBENZOIC ACI 01N-AMYL ESTER P-AMINOBENZOIC ACIOePENTYL E S T E R NIN-DIMETHVLCARBAMIC ACIOtM- I-PRDPYLPHENYL E S T E R N-METHYL C A R B A M A T E I ~ - I - P R O P Y L I ~ - ~ E T H Y L P H E N Y L N-METHYL C A R B A H A T E I ~ - S - ~ U T Y L P H E N Y L N-METHYL CARBAMATEI~-T-~UTYL PHENYL N-METHYL-2-S-BUTYLPHENYLCARBAMATE N-MElHYL-2-T-BUTYLPHENYLCAR8AMATE N-METHYL-3-METHYL-4-I-PROPYLPHENYLCARBAMATE N-METHYL-3-METHYL-5-I-PROPYLPHENYLCARBAHATE N-METHYL-3-METHYL-6-I-PROPYLPHENYLCARBAMATE N-METHYL-3-T-BUTYLPHENYLCAR8AMATE N-METHYL-4-S-BUTYLPHENYLCARBAMATE N-METHYL-4-T-8UTYL PHENYLCARBAMATE PHENOXY ACETAMI OEtN .N-0 IETHYL P-AMINOSALlCYLIC ACI0.N-AMYL ESTER N-METHYL-3-8UTOXYPHENYLCAR8AMATE P-AMINOSALICYLIC ACIOI~-HYOROXYAMYL ESTER GLUCOPYRANOSIOEI~-AMINOPHENYL (BETA) GLUCOPYRANOSIOEI~-AMINOPHENYL (BETA1 3-PYRIOYLETHYL-2-lN-PIPERIOINE~ OXO-TREMORINE UREA, N-BUTYL r O-TOLYLUREAvN-8UTYL.P-TOLYLBENZOIC A C 1 0 t P - M E - A M I N O I N I N - D I M E T H Y L A M I N O E T H Y L ESTER BENZOIC A C I O I P - M E - A M I N O I N I N - O I M E T H Y L A M I N O E T H Y L ESTER ESTER BENZOIC A C I 0 . P - M E - A M I N O I N I N - O I M E T H Y L A M I N O E T H Y L ESTER BENZOIC A C I O I P - M E - A M I N O I N I N - O I M E T H Y L A M I N O E T H Y L BARBITURIC ACID. 5 - A L L Y L - 5 - I - A H V L ~ 2 - T H I O BAR8ITURIC A C I O I ~ - A L L Y L - ~ - I - A M Y L I ~ - T H I O BARB I T U R I C AC 10*5-ALLYL-5-I-AMYL 92-THI 0 BARBITURIC ACID, +ALLYL-%( 1-HEBUTYL 12-THIO BARBITURIC A C I O I ~ - A L L Y L - ~ I ~ - M E B U T Y Lv2-THIO ~ BARBITURIC A t 1 Ot 5-( CYCLOHEX-l-YL I , 5-ET12-THI 0 I1 ) BARBITURIC A C l D t 5-(CYCLOHEX- 1YL I-5-E 1-2-THIO 8ARBITURIC ACID. 5-1 CYCLOHEX-1-YL ) r 5-ET92-THIO ( 1I BARBITURIC ACIOv 5-ALLYL-5-1 1-MEBUTYL I /SECOBARBITAL/ THIAMINE PYROPHOSPHATE /COCARBOXYLASE/ METHYL ETHYL AMPHETAM I N E METHYLETHYL AMPHETAMINE N-PROPYL-G-PHENYLPROPYLAHINE PROPYLAMPHETAMINE PROPYLAMPHETAMINE PROPYLAMPHETAM INE I PROP Y L AMP HE T AM 1N E I-PROPYLAMPHETAM I N E PKOCARBAZINE HYDKOCHLORIOE ( 7 7 2 1 3 1 (PKA= 6.661 O~O~OIETHYL~O-~3-ME-4-METHIOPHENYLlPHOSPHAlE OIO-DIETHYL-O-~~-ME-~-MESULFDNYLPHENYLJPHOSPHATE G-PHENYLPROPYL-TRIMETHYL-AMMONIUM IODIDE 0 Nv N-0 1 I -PROP Y L- 3- PRY I Y L M E 1HYLA M I NE NI N-01 PROPYL-3-PYR IOYLMETHYLAMINE BARBITURIC ACI DI 5- I 1-M E8U)-5-( 2-ME THIO1 -2-THI 0 BARBITURIC ACID, 5-1 1 - H E B U 1 - 5 - 1 2 - M E T H I O I - 2 - T H I O BAR8 I T UR IC A C I 0 ~ 5 E 1-5- I - A M Y L-N- ME THYL BARBITURIC A C I D v %ET- 5-I-AMYL-N-ME THYL 8ARBITUR I C A C I 5- ET- 5- I - A M Y L-N-ME THYL De C I T R I C A C I O ~ T R I E T H Y L ESTER C I K I C A C 101 TRIETHYL ESTER T T R I - ( 2 ~ 3 - 8 U T A N E D I O N E O X I M E l COBALT GLUCOPYRANDSIDEICYCLOHEXYL (BETAI MALTOSE SUCROSE 2-AZATRIOECANONE P I P E R I O I N Y L FORMIC ACIOiDIETAMINOETHYL ESTER DOOECANOIC AC 1 O/L AUR IC A C IO/ DOOECANOIC ACIDILAURIC A C I D / ARGI NYLLEUC INE DOOECYL SULFATEISDOIUM SALT NEAMINE/NEOMYCIN A / ( A S 2-ETHYL BUTYRATE) 1-WOECANDL TETRAETHYLENE GLYCOL DIETHYL ETHER
3
438 4 125 396 396 418 390 376 391 391 391 384 384 384 384 384 38 4 384 384 142 370 384 370 438 438 341 400 419 4 19 449 449 449 449 399 399 399 218 142 399 399 399 125 181 396 396 374 396 138 396 396 396 227 437 437 255 341 341
=
8
C12H17N102 C12H17N102 C12 H17N102 ClZHllNlOZ C12H17N102 C12H17N102 C12H17N102 C12H17N102 C12H17N102 C12H17N102 Cl2Hl7NlOZ C12H17N102 C12H17N102 ClZH17N102 C12H17N102 Cl2H17N103 C12H17N103 ClZH17N104 C12 H 1 7 N 1 0 6 C12H17N106 ClZH18N2 C12H18N201 .HCL C12H18N201 C 12 H18 N 2 O l ClZHl8NZO2 C12H18N202 CIZH18N202 C12H18N202 C12 H1 8NZOZS 1 ClZH18N202Sl C12H18N202S1 C12HlBN202Sl ClZH18N202Sl C12H18N202Sl C12H18N20251 C12H18N202Sl C12H18N203 ClZH19CLlN407P2Sl C12H19Nl C12H19N1 C12H19N1 Cl2H19N1 C12H19N1 C12H19N1 C12H19N1 Cl2H19Nl C12 H19N301. H l C L 1 C12 H 1 9 0 4 P l S 1 C12H1906PlSl ClZHZOIlNl ClZH2ON2 C 1 2 H2 0 NZ C12 H20 N 2 0 2 5 2 C12 H2ON2OZS2 C12 HZ ON2 03 C12 HZON203 C12H2ON203 C12H2007 C l Z HZ007 C12HZlN606C01 ClZH2206 ClZH2ZOll C12H22011 C12 H2 3N 1 0 1 C12H24N202 C 1 2 H2 4 0 2 C12H2402 C12H25N503 ClZH25NA104Sl C 1 2 H26 N4 06 C12H2601 C12H2605
2.78 2.65 3.11 3.10 2.84 2.93
= = = =
= =
3.20
3.06 2.02 2.96 -2.67 -1.23 1.66
= =
=
-1.23
1.66 -1.40 0.35 0.12 1.95 0. YO 1.38 1.01 2.84 1 3.23 1 1.84 1 3.23 2.50 2.27 1 2.75 1.17 0.62 1 0 -0.15 3.68 31 31 2.22 2.11 31 3.91 2.56 2.49 31 3.65 31 2.07 31 0 06 . 2.73 2.82 -2.02 60 2.27 60 1.46 2.00 2.04 2.74 1 2.61 1 1.95 1 0.65 60 14
1.95 2.01
=
A
3.30
3.17 3.43 3.23 3.04 2.75 2.67 2.80 2.34 2.92 2.71 3.12 2.90 0.06 2.73 2.82 2.27 1.46 2.38 3.04 2.15 2.52 0.67 0.97 0.13 -0.63 -3.88 -3.67 1.72 0.62 -1.56 1.60 -0.13 5.13 -0.95
N
A
=
N
A
8
8
8
=
= =
=
=
N A 8
A A
322
442 399 399 399
3
2 263 438 4 4 260 378 218 139 84 268 450 218 2
-0.30
0.41 -C.63 -2.40 -2.25 1.72 -0.36 4.20 3.03 -0.15 1.60 0.25 5.13 -1.21
= =
8
44 26 31 19 32
= =
A
NO. 4501 4502 4503 4504 45c5 4506 45c7 4508 4569 4 5 10 4511 45 12 4513 45 14 4515 4516 45 17 4518 4519 4520 4521 4522 4523 4524 4525 4526 4527 4528 4529 4530 4531 4532 4533 4534 4535 4536 45 37 4538 4539 4540 4541 4542 4543 4544 4545 4546 4547 4548 4549 45 SO 4551 4552 4553 4554 4555 4556 4557 4558 45 5 9 4560 4561 4562 4563
SOLVENT CHCL3 TOLUENE OCTANOL 5OIETHER+5OIOHF CYCLOHEXANE CYCLOHEXANE O C T ANOL OILS OCTANOL OCTANOL 0 C T ANOL OCTPNOL N-C E PT ANE OCTANOL OCTANOL OILS OCTANOL OILS OC TANOL OILS OCTANOL OILS OCTANOL PARAFFINS CYCLOHEXANE OCTANOL OCTANOL OCTANOL CHCL3 BENZENE TOLUENE TOLLENE TOLUENE PARAFFINS OCTANOL OCTANOL N-HEPTANE OCTANOL N-IEPTANE N-HEPTANE OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE TOLUENE CCL4 CHCL3 CCL4 OCTANOL OCTANOL HEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE HEXANE DIETHYL ETHER CHCL3 CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL DIETHYL ETHER CHCL3 CHCL3 I-PENT. ACETATE CCL4 CHCL3 CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL HEXANE CHCL3
REF FOOT NOTE 451 452 268 125 304 304 427 453
LOGP SOLV 2.05 0.58 1.85 0.34
LOGP OCT 1.52 1.04 1.85 1.65 3.40 3.29 -0.27 0.77 -0.38 -0.50 4.70 2.47 2.92 2.62
EMPIRICAL FORMULA
NAME
T R IBUTYLAMINE TRIBUTYL PHOSPHINE OXIDE OODECYLAHINE HYOROCHLORIOE BARBITURIC ACID, 5-ETHYL-5-PHENYL-N-METHYL MALONONITRILEI~-TRIFLUOROHETHYLC~NNAMAL 9-FLUOR ENON E AC RI 01 NE ACRIDINE P-BIPhENYLCARBOXYLIC ACID, SOOILM SALT BIPHEVYLCARBOXYLIC ACID. SOOIUH SALT BIPHENYLCARBOXYLIC ACID. SOOIUH SALT ACRIDINE HYOROCHLOR I O E PHENOTHIAZINEt 2-CHLORO v7-METHOXY UREA, 1-1 31 4-OICHLOROPHENYL)-3-PHENYL 1-AHINOACRIO INE 1-AHINOACRIOINE 2-AMINOACR I O I h E 2- A INC ACR I O l \ E H 3-AH INOACR I O 14E 3-AMINOACRIOINE 4- A INOACR I O l h E H 4-AHINOACRIOIVE 9-AH I h O A C R I O I \ E 9-AHlNOPHENAhTHR 10 INE ETHYLCYAhOACETATE,C-CVANOBENZAL PHTHAL IH I DEI N- 1 2 1 6-010 XO- 3-P [PER IDYL ) BENZOPdEhONE BEhZOPhE%ONE 1- 12-SELENOPHEN-YL I-3-PHEhYL-1 t 3-PROPAhEOI ONE 1-12-SELEhOPHEN-YL ) - ~ - P ~ E N Y L - ~ I ~ - P R O P A ~ E O I C ~ E CUPROUS-CAXBAZONE COMPLEX HERCcJRlC-CARBAZJhE COMPLEX MERCUROUS-CARBAZOhE COYPLEX 2-AMINOFLUORENE BE hZAN I L I O E SALICYLALDEHYDE-AhIL PH NOT H I A Z I NE, 3-HETdOXY SALICYLAhIL IO Pn EhOT H I A 2 I N E 1 3-HE THY L PtlENOThIAZIhE~ 10-METHYL 21 8-OIAMIhOACRIOINE OIPHENYLHETnANE ETHYLACETOACETATE. 2.6-OICHLOROBENZAL ET MLACETOACETATE. 2 1 4- 0 ICHLOROBENZAL ETHYLACETOACETATEt 3r4-0ICHLOROBENZAL
12
46
2.28
2.98 3.40 50 71 72 73 46
=
A
2.30
-0.27 0.77
283
283
= =
0
283
216 443 218 346 453 346 453 346 453 346 453 216 439 304
-0.38
-0.50 1.42 4.70 2.47 1.79 2.62 1.97 2.19 1.87 3.26 3.08 2.74 0.85 1.29
= =
=
A
=
A
3.08
2.19 3.00 3.26 4.00 2.74 0.33 3.18 3.18 4.76 4.94 2.50 1.21 2.10 2.62 3.09 3.27 1.10 4.14
=
A
12
=
A
12
=
* = =
A A B B
218
2 35 235 3 88
0.33
3.18 3.18 3.90 3.66
388
148 148 148 3 16 56 9 443
2.52
0.81
2.00
26
1.76 2.62 3.09 2.43 3.27 3.23 4.58 1.10 4.14 1.91 2.98 4.00
8
= = = =
238
443 443 346 235 304 304
3 04 304
454 454 455 203 276 428 456 304 12
3.33
1.59
0.88
5.90 1.61 2.03 2.67 0.56 2.03 2.67
C 12 H2 7N 1 C12 H270 1P 1 C12H28CLlNl C13N14N203 C13H7F3NZ C13H801 C13H9N1 C13H9N1 C13 H9N A 102 C13 H9NA 102 C13H9NA102 Cl3HlOCLlNl C13H1OCL1N101Sl C13H10CL2N201 Cl3H10N2 C13H10NZ C13H10N2 C13H10N2 C13HlONZ C13H10NZ C13H10N2 C13H10NZ C13H10N2 C13HlONZ C13HlON202 C13 H10N204 C13H1001 C13H1001 C13H1002SEl C13H1002SE1 C13H1 I C U 1N401 C13HllHG1N401 C13HllHGZN401 C13HllN1 Cl3HllNlOl ClBHllNlOl C13HllN101Sl C13HllN102 C13HllNlSl C13H1 l N l S l C13HllN3 C13HlZ C13H12CL203 C13H12CL203 C13H12C L 2 0 3 C13H12N201 C13H12N401 C 13H12 N 4 0 1 C13HlZN4Sl
HALONONITRILE.2-I-PROPOXYBENZAL
OIPHENYLCAROAZONE DIPHENYLCARBALONE OIPHENYLTHIOCARBAZONE/OITHIZONE/ OIPHENYLTHIOCAR8AZONE/OlTHIZONE/ OIPHENYLCAR8INOL OIPHENYLCARBINOL GR ISAN-3r4'-OIONE ETHYL ACETOACETAT E, 3-FLUOROBENZAL ETHYLCYANOACETATEt 2-HETHYLBENLAL ET WLCYANOACETATEI 4-HETHYLBENZAL N-ME-N-PROPIONYLCARBAMIC ACIOI~-BENZOTHIENYL ESTER N-P-TOLUENEBENZENESULFONAHIOE
=
=
304
304
2.23 3.26
3.62 2.45 0.67 0.43 2.47 2.68 0.70 1.77
376
113 113 304 304
A A
N-P-TOLUENEBENZENESULFONAHIOE
ET HY LCY ANOACET AT E. 4-ME THOXY8ENZ AL ET H LCY ANOACETATE. 2-METHOXYBENZAL Y ETHYLCYANOACETATE, 3-HE THOXYBENZAL 8-PHENYLETHYLPYRIOINIUM BROMIDE lr4-NAPHTHOPUINONE~2-I-PROPYLHYORAZINO N1-(4-HETHYLPHENYL JSULFANILAMIOE BARBITURIC A C I O I I - M E ~ ~ - E T . ~ - P H E N Y L BARBITURIC ACID, l-MEs 5-ET.5-PHENYL BARBITURIC ACIOI I-MEI~-ET.~-PHENYL N1-(3-HETHOXYPHENYL)SULFANlLAHIOE ACETYLACETONEvZ-METHYL BENZAL A ET Y L A C TON 9 4-MET HY1 8EN2 AL C ACETYLACETONEI 4-HETHOXY-BENZAL AC ET Y L A C ETONE1 2-ME THO X Y-8 EN2 AL ACETYLACETONEt 3-METHOXY-BENZAL ETHYLACETOACETATEI BENZAL GLUCOPYRANOSIOEI~-TRIFLUOROHETHYLPHENYL~~ETA~ GLUT A I H I DEI 2-ETHYL-2-PHENYL R N-HECARBWIC ACl010-CYCLOPENTENYLPHENYL ESTER OIL-TYROSINE.O~N-DIACETYL N- ACET Y L-4-AH I N 0 ANT I P Y R INE N-ACETYL-4-AHINOANTIPYRINE N-ACETYL-4-AHINOANTIPYRI" BENZOIC A C 1 0 1 4 - 0 H ~ 3 ~ 5 - 0 1 - 1 0 0 0 ~ H E X Y LESTER ESTER BENZOIC ACIOt 3 1 5-DI-1000-4-0H16-OH-HEXVL BARBITURIC ACID. l - A L L Y L - 5 * 5 - 0 I A L L Y L PHENOXYACETIC ACIO.4-CYCLOPENTYL N-HETHYLCARBAMIC ACIOeO-CYCLOPENTYLPHENYL ESTER ST YRENEI 4-I-PROPYL I8-N I TRO*B-ETHYL ~~~AIA~OIETHYLACETAHIOO~~I~~-~ENZOOIOXOLE N-METHYL-N-ACETYLCARBAMIC ACIOik+I-PROPYLPHENYL ESTER N-HE-N-ACETYLCARBAH I C AC IO r O- I- PROPOXYPHENYL ESTER STVRENE~3r4~OIETHOXY~B~HETHYL~B~NITRO AMINOPYRINE A INOPVR I N M AH INOPYRINE AM INOPYR I N AM INOPYR INE AHfNOPVRINE AMINOPYRINE AMINOPYRINE
304 65
451 444 399 399 399
28 .0
46 62 -2.35 0.39
4564
45.5 5 4566 4567 4568 4569 4570 4571 4572 4573 4514 4575 4576 4577 4578 4579 4580 4581 45a2
30 1 1 1
30
2.00
1.98 1.75
-2.35 0.46 2.47 1.37 1.64 2.13
=
A N B
N C13H14N203 C13H14N203 C13H14N203S 1 C13H1402 C13H1402 C13H 1 4 0 3 C13Hl403 C13H1403 C13H1403 C13Hl5F306 C13H15N102 C13Hl5N102 C13H15N105 C13H15N302 C13H15N302 Cl3H15N302 C13H16 I 2 0 3 C 1 3 H I 61 2 0 4 C13 H16N203 C13H1603 C13H17N102 C13H17N102 C13H17N103 C13H17N103 C1 3H l 7 N1 0 4 C13H17N104 C13Hl7N301 Cl3H17N301 C13H17N301 C13H17N301 C13Hl7N301 C13Hl7N301 C13Hl7N301 Cl3Hl7N301
0.80
1.64 1.52 1.57 0.91 1.04 1.06 2.03 0.49 1.90 1.15 -0.84
444 304
304 304
304
304
304 438
218 376 67 338 330
0.49 1.90
= =
B
A A
44
01 .8
-2.70 -2.40 6.02 3.30 1.18 3.41 1.38
-0.08
66 .6 4.19
3.41 1.59
44
44 24 24
45aa
4504 45e5 4586 4587 4588 45 89 4590 4591 4592 4593 4544 4595 4596 4547 4548 4599
338 382
382
433 10 376 141 458 376 376 141 218
= =
4600
CYCLOHEXANE OCTANOL HEXANE HEXANE CYCLOHEXANE OCTANOL 01 ETHYL ETHER CHCL3 CHCL3 OILS BENZENE BENZENE N-HEPTANE
28 .9
1.59 2.53 1.84 2.45 0.80 -0.20
0.80
0.67 1.36 1.03 0.71 1.12
3 330 405 2
338 405 254
44
44
18 .6
1.47 -0.59
0 A
-0.40
0.83
-0.68
Chemical Reviews, 1971,Vol. 71, No. 6 601
NO. 4601 4602 4603 4604 4685 4606 4607 46C8 4609 4 6 10 4611 4612 4613 4614 4 6 15 4616 4617 4 6 18 4 6 19 4620 4621 4622 4623 4624 4625 4626 4627 4628 4629 4630 4631 4632 4633 4 6 34 4635 4636 4637 4638 4639 4640 4641 4642 4643 4644 4645 46 46 4647 46 48 '4649 4650 4651 4652 4653 4654 4055 4656 4657 4658 4 6 59 4660 4661 4662 4663 4664 4665 4666 4667 4668 4669 4 6 70 4671 4672 4673 4674 4675 4676 4677 4678 4679 4680 4681 46@2 4683 4684 46t5 4686 4687 4688 4689 4690 4691 4692 4693 4694 4655 4656 4697 4698 4699 4700
SOLVENT N-HEPTANE N-HEPTANE OLEYL ALCOHOL N-HEPTANE N-HEPTANE C ~ C3 L CHCL3 CHCL3 CHCL3 5 0 I ET HER +50 XDM F CHCL3 I-PENT. ACETATE CCL4 OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL 0 CT ANOL OCTANOL I-BUTANOL OLEYL ALCOHOL 0 CT ANOL OCTANOL OCTANOL N-HEPTANE OLEYL ALCOHOL N-HEPTANE OCTANOL OLEYL ALCOHOL OLEYL ALCOHOL OCTANOL OILS XYLENE 01-BUTYL ETHER DIETHYL ETHER OCTANOL OCTANOL DIETHYL ETHER CHCL3
REF FOOT NOTE
LffiP SOLV -0.82 -0.68 0.11 1.17 3.45 0.36
L06P OCT
EMPIRICAL FORMULA C13Hl7N301 C13Hl7N301 C13H17N301 C 1 3 H l B C L 1N103 C13H18F3N1 C13Hl8NZOl C13H18NZ01 C13H18NZOl C13H18N201 C13H18 NZ03 C13H18N203 C13H18N203 C13H18N203 C33H1803 C13H1806 C1 3 H 1 8 0 6 C13H1806 C13H1806 C13H1807 C13H1807 C13H1807 C13H1807 C13H1807 C13H19N102 C13H19 N102 C13H19N102 C13H19N102 C13H19N103 C13H19N103 C13H19N 1 0 4 C13H20CLlN2 C13 HZO N2 0 1S 1 C13H20N202 C1 3 H20 N2 02 C 13HZO N202 C13H20N202 C13HZON202 C13H20N202 C13HZO N202 C13H20N202 C13H20N202 C13H20N202 C13HZON202 C13HZOhZOZ C13HZON202 C13HZON202 C 13H20N202 C13 HZ008 C13 HZ008 C13HZlCLlNZOI C13HZ 1N 1 C13 H2 1N 1 C 13 HZ 1N 1 C13HZlNl C 13HZ 1N 3 0 1 C 13HZ 1 N 3 0 1 C13HZZBRlN 1 C13H22BRlNl C13 H22 NZ 0 1 C13H22N201 C13H2ZN20251 C 13 HZZN2S1 C13 H2 3N 1 0 2 C 1 3 H 2 6 I LNLOZ C13H2611N102 C13H26N202
NAME
3 38
340 82 416 138 448 448 448 448
44
14
65 65 65 65
0.67
0.52
1.45 1.92
125
399 399 399 56 438 438 438 438 438 438 438 438 4 390 384 384 384 370 142 370 276 459 460 449 449 449 449 378
0.57 0.98 0.26 2.48 1 2.27 1 1.49 1 4.35 -0.70 -0.20 -0.16 -0.16
2.18
4.35 -0.70
-0.20
-0.16 -0.16
= = =
=
5
-1.22
-1.04 -0.73 -0.52 -0.40 3.71
-1.22
-1.04 -0.73 -0.52 -1.07 4.25 3.35 3.14 1.45 4.14 3.14 2.45 2.62
=
=
44
3.38
14 14 3.35 3.14 1.40 0.89 0.50 4.14 2.57 1.90 2.62 1.46
3.38 =
= = =
A
31
2.52
1.38 1.87 1.92 1.71 2.08 1.93
2.20
44 1.65 0.50 1.87 1.92
218 218
461 405 462 4 459 235 235
= =
A
18 .1
31 31
2.66 1.82 1.80 1.79 -2.24 0.16 0.97 0.97 -0.67 2.43 3.10 4.05 2.30 1.27 1.22 -1.85 -0.95 1.65 2.32 1.13 2.90 0.85 -2.85
8
B
2.03
2.35 -2.24 0.16 1.70 0.87 -0.67 3.02 3.24 1.84 1.77
= =
8 8 B
3
4 OCTANOL DIETHYL ETPER N-HEPTANE CHCL3 N-HEPTANE OLEYL ALCOHOL O L E Y L ALCOHOL OCTANOL OCTANOL OLEYL ALCOI-OL OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOhOL OCTANOL CHCL3 CHCL3 OIETHYL ETHER OCTANOL OCTPNOL OCTANOL CYCLOHEXANE CYCLOHEXANE 01 ETHYL EThER HEXANE OCTPNOL 0 CT ANOL OILS OCTANOL OCTANOL OCTANOL OCTANOL PARAFFINS CYCLOHEXANE CHCL3 CHCL3 PARAFFINS OCTANOL CYCLOHEXANE OCT ANOL OCTPNOL DIETHYL ETI-ER CHCL3
CHCL~
373
374 138 396 396 459 459 65 65 459 459 459 4 59 348 424 424 378 2 68 268 297 304 141 143 317 427 427 ,224 463 463 463 463 316 141 464 464 439 31 31 31
31
46 53
-1.85
-0.95
= =
31 .3 1 31
31 46 46 44 46 46 46 62
2.22
2.89 1.68 3.47 0.85 0.32 1.15 -0.16 3.93 4.45 4.46 4.24 2.69 2.46 0.89 2.12
A
=
8
-2.00
0.70
1.15 1.00
-0.16
= 1.00 =
3.01
1.39 4.35 4.96 4.45 4.46 4.60 2.69 2.46 0.89 2.12 1-06 4.40 4.96 5.86 1.36 2.99 -2.31 3.97 2.06 2.50
= = = = =
=
8
46 46
10
141 2 35 463 46 29 46 46 29 10 276 465 276 443 3 70
2.99 3.97 2.06 2.32 2.20 1.99 1.74 1.88 3.18 4.28 2.49 2.90
= = =
A
1.08
0.85 -0.04 0.34 3.18 4.28 2.70 2.90 2.83 1.52
XYLENE TOLUENE OCTANOL OCTANOL OIETHYL ETI-ER OCTbNOL N-I-EPTANE N-I-EPTANE
A A A A
=
A
62 14
AMINOPYRINE AMINOPYRINE AMINOPYRINE P-AM I NOS AL I CYL I C AC 101bCHLOROHE XYL ESTER N-PROPYLNORFENFLURAMINE NI N-OIMETHYLTRYPTAMINE s4-METHOXY N N-OIMETHYLTRYPTAMINE 15-METHOXY I N~N-OIHETHYLTRYPTAHINEI6-nETHOXY N.N-OIMETHYLTRYPTAMINEI~-METHOXY BARBITURIC ACIDI 5 - I l - C Y C L O H E P T E N - l - Y L l - 5 - E T H Y L CYCLOBARBITAL,N-METHYL CY CLO8 AR 8 I TAL N-METHYL CY CLOBARBI TAL, N-METHYL P-HYOROXY8ENZOIC ACIOIHEXYL E S T E R GLUCOPYRANOSIOEeBENZYL (BETA1 GLUCOPYRANOSIOE.3-METHYLPHENYL (BETA) GLUCOPYRANOSIOEIZ-HETHYLPHENYL (BETA1 GLUCOPYRPNOSIOE,4-METHYLPHENYL 18ETAl GLUCOPYRANOSIOE, 2-HYDROXYHETHYLPHENYLI BETA1 GLUCOPYRANOSIOEI~-METHOXYPHENYL (BETA1 GLUCOPYRANOSIOE.4-METHOXYPHENYL IBETAI GLUCOPYRANOSIOE~3-METHOXYPHENYL IBETAI GLUCOPYRANOSIOEISALICYL ALCOHOL P-AMINOBENZOIC ACIOt HE XYL ESTER N-METHYL-3-METHYL-4-1BUTYLPtiEkYLCAR8AHA TE N-METfiYL-3-METkYL-5-T-8UTYLPHENYLCARBAHATE N-METHYL-3-METHYL-b-T-BUTYLPHENYLCAR8AMATE P-AMINOSALICYL I C ACIDIN-HEXYL ESTER 2-METHOXY-PHENOXYACETAMIOE ,NIN-OIETHYL P-AMINOSALICYLIC ACIO.6-HYDROXYHEXYL ESTER N-01 ETHYLAH INOETHYLANILINEI 3-CL-4-METHYL /PKA= 9.6/ THIOCAINE P-AMINOBENZOIC ACIO~OIETHYLAMINO-ETHYL ESTER BENZOIC ACIOIP-ET.AHINOININ-OIHETHYLAMINOETHYL ESTER ESTER BENZOIC A C I 0 , P - E T - A M I N 0 , N . N - O I M E T H Y L A H I N O E T H Y L ESTER BENZOIC ACIOsP-ET-AHINOININ-OIMETHYLAMINOETHYL BENZOIC A C 1 D . P - E T - A M I N O I N ~ N - O I M E T H Y L A M I N O E T H Y L ESTER N-PHENYLCARBAMIC ACIOIOIETAMINOETHYL ESTER PR OC A I NE PR O A 1NE C PROCAINE /NOVOCAINE/ PROCAINE /NOVOCAINE/ PROCAINE PROCAINE PROCAINE /NOVOCAINE/ PROCAINE I P I 3 8 ;PKAI 1I= H . 8.96: PKAI 2 l = 2 . 0 1I PROCAINE lPH=7.30;PKA=8.961 PENT AER I THR ITOL TETRA-ACETA TE PENTAERITHRITOL TETRAACETATE Nl-HEPTYLNICOTINAHIOE CHLORIDE N-BUTYL-G-PHENYLPROPYL AMINE N-BUTYLAHPHETAHINE METHYL-I-PROPYLAMPHETAHINE METHYL-I-PROPYLAHPHETAMINE 8-0IETAHINOPROPIONAMIOE~N-~P-AHINOPHENYLl PROCAINEAHIOE BENZVLDIMETHYL8UTYLAMHONIUM BROMIDE OCTYLPYRIOINIUM BROMIDE P-AHINOBENZYL. 01 ETHYL AH I N 0 ETHYL ETHER P-AMINOPHENYL. 01 ETHYLAHINOPROPYL ETHER P - A H I N O P H E N Y L I O I E T H Y L A M I N O P R O P Y L SULFONE ANILINE.4-OIETHYLAHINOPROPYLHERCAPTO N-OCTANOYLCYCLOBUTANEC ARBOXAHIOE Ir2rZibtb-PENTAMETHYL-4-ACETYL PIPERIDINE ME1 l r 3 r 3 r 515-PENTAHETHYL-4-ACETYL P I P E R I D I N E ME1 N-CYCLOHEXYLCARBAHIC ACIO~OIETAHINOETHYL ESTER OOOECYLGUANIOIUH ACETATE OODECYLGUANI O I N E HVDROBROM I O E C13H301 I N 1 TRIMETHYL-OECYL-AMMONIUM IODIDE C14H802 ANTHROPU INONE C14H802 PHENANTHRENEPUINONE C 14H803S 1 2-HYOROXYNAPHTHOPUINONE~3-1 Y-A-THI ENYLPROPYL I C 14H9CL5 DOT ci4ni0 ANTHRACENE PHENANTHRENE C14H10 PHENANTHRENE C14H10 9-CARBOXYFL UOREN E C14H1002 C14H1002Sl 9-CARBOXYXTHIOXANTHENE C14H1003 9-CARBOXY-9-HYOROXYFLUORENE C14H1003 9-CARBOXYXANTHENE 9-AMI NOPHENANTHRENE C14H11N1 FLUORENE.9-NITROMETHYLENE C14H11N 1 0 2 C14H12Nl.ClOH2104S1 N-METHYL ACR I O I N IUH OECYL SULFATE C l 4 H l Z N l .ClZH2304S 1 N- MET HY L ACR I D I N 1U DO O E C YL SULFATE M C14H12N2 9-AMINO-3-HETHYLPHENANTHRIDINE C 14111 2 h 2 0 3 PHENOXYACETIC ACIOv4-PHENYLAZO C141i12h204 lr4-NAPHTHOOUINONE~2~3-OIACETAMIOO BENZYL BENZOATE C14H1202 Clcr~l202 AI A-01 PHENYLACET IC AC I O C14ti1203 BENLILIC A C I O C14ti1203 B E N Z I L I C ACIO C14ti1203 BENZILIC A C I O C14HlZ03 B E N Z I L I C ACIO Cl+H1203 B E N Z I L I C ACID C14fi1203 PHENOXY ACE1 IC AC 1 0 9 H-PHENYL C14H120351 2-OH-3-CARBOXYBENZTHIOPHENYL ETHER /PKA * 3.00/ Cl4H1205 2-HYOROXYNAPHTHOPUINON E t 3- I 2-CARBOME THOX Y THYL ) E Cl4H13N1 OIHYOROMORPHANTHRIOINE /PKA = 3.00/ C14H13N102S1 PH ENOT H I A2 I NE, 31 7-DIHETHOXY C14H13N103 P-AMINOSALICYLIC ACIDvBENZYL ESTER
602 Chemical Reviews, 1971, VOl. 71, No, .6

SOLVENl 4701 4702 4703 4704 47c5 47C6 47c7 47C8 4709 4710 4711 4712 4713 47 14 4715 4716 4 7 17 4718 4719 4720 4721 4722 4723 4724 4725 4726 4721 4728 4729 4730 4731 4732 4733 47 34 4735 4736 4737 4738 4739 4740 4741 4742 4743 4744 4745 4746 4747 4748 4749 47 50 4751 4752 4753 4754 4755 4756 4757 4758 47 59 4760 4761 4762 4763 4764 4765 4766 4767 4768 4769 47 70 4771 4772 4773 4714 4775 4776 4777 4778 4779 4780 4781 4782 4783 4784 4715 4786 4787 4718 4789 4190 4791 4792 4793 4794 4795 4796 4797 4798 4799 4800 HEXANE N-HEPTANE OCTANOL OCTPNOL OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CHCL3 OCTANOL CYCLOHEXANE DIETHYL ETCER DIETHYL ETkER DIETHYL E T k E R CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE DIETHYL ETCER CYCLOHEXANE CHCL3 HEIANE PARAFFINS PARAFFINS PARAFFINS 0 1 ETHYL ETCER CHCL3 HEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CHCL 3 BENZENE TOLUENE NITROBENZENE N-BUTYL ACETATE CCL4 ME-I-BUT.KETONE OCTANOL 01 ETHYL ETNER 0 1 ETHYL ETkER OCT PNOL CHCL3 MIXED S O L V I l OCTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL CHCL3 OILS OCTANOL OLEYL ALCOHOL OILS N-HEPTANE N-HEPTANE CHCL3 CHCL3 OCTANOL OCTANOL OCTANOL OLEYL ALCOHOL HEXANE N-HEPTANE N-HEPTANE OCTANOL OLEYL ALCOHOL OLEYL ALCOCOL OLEYL ALCOHOL OCTANOL OILS XYLENE 01-BUTYL ETHER DIETHYL ETkER DIETHYL ETHER DIETHYL ETkER DIETHYL ETtER DIETHYL ETHER DIETHYL ETKER 01-I-PR. KETONE OCTANOL OLEYL ALCDHDL OCTANOL N-HEPTANE REF FOOT NOTE 391 44 3 218 276 65 141 141 141 235 444 141 141 143 143 143 304 304 304 LOGP SOLV 2.19 4.08 4.79 4.82 -1.56 2.67 4.26 2.64 -1.78 1.43 3.29 3.43
LOGP oc T
EMPIRICAL FORMULA C 14H13N 1 0 3 C14H13NlS1 C14H14 C14H14 C14H148RlNl C14H148RlNlOZ C14H14CL 1N1 0 2 C14H14CLlN102 ClCH14CLlN3.HCL C14H14h203S 1 Cl4ii1402Sl C14H1402Sl C14H1403 C14H1403 C 1 4 H1404 C14H1405 C14H15C L 1 0 4 C14H15F104 C14H15F104 C14H15F104 C 14H15N 1 Cl4Hl5N1 Cl4H15N1 C14H15N1 C14H15N1 C14H15Nl C14H15N101 C14Hl5N101 C14H15N101 C14H15N101 C14H15N102 C14H15N 1 0 2 C14H15N 1 0 2 s 1 C14H15N 1 0 4 C 14H15N104 C14H15N104 C14H15N106 C14H15N106 C14H15N106 C14H15N3 C14H1504Pl C 14H1504P 1 C14H1504P1 C14H1504P1 C14H1504Pl C14H1504Pl C14H1504Pl C14H168RlNl C14H16NZO2 C14H16N202 C14HlbNZOZSl C14HlbN202Sl C14H16N205 C14H16N402S1 C14H1603 C14H1603 C14H1603 C14 H1604 C14H1604 C14H1604 Cl4H1604 C14H17F3N201 C14Hl7N101 C14H17N101 C14H17N309 C14H18N202 C14Hl8N203 C14H1803 C14H19N103 C14HZOBRlN101 C14HZOCLlNlO3 C 14HZOF3N1 C14H20NZ C14H2ON201 C14H2003 C14H2006 C14HZ006 C14H21N102 C 1 4 H Z l N 102 C14H2 1N 103 C 1 4 H2 1 1 0 4 N C14HZlN302 C14H22N201 C14H22N202 C14HZ2N202 Cl4H22N202 Cl4H22N202 C14H22N202 C14HZZN202 C14H22N202 C 14H22N202 C14H22N202 C14HZ2N203 C14H22N203 C14H22N203 Cl4HZ2N407 C14H23CLlN201 C14H24N2 C14H24N2 C14H2802
NAME N-METHYL CAR8AMATEvN-ACETYL.l-NAPHTHYL PHENOTHIAZIMEI 3.7-DIMETHYL 8 1 BENZYL 1.2-OIPHENYLETHANE C 1NN AMYL PY R IO I N I M BROM I DE U lr4-NAPHTHOQUINONE~Z-8ROMO~3-8UTYLAMINO 1v 4-NAPHTHOQU I NONE t 2-C HLORO- 3- B UTYLAH 1NO 1~4-NAPHTHOPUINONEt2-CHLORO~3-8UTYLAMINO ACRI FLAVINE HY OROCHLOR I DE N1-13-ACETYLPHENYL ISULFANILAMIOE ~~~-NAPHTHOQUINONEV 2-BUTYLTHIO l r 4-NAPHTHOQUINONE~Z-MUTYLTHIO 2- HY OR O X Y NA PHT HO P U I NON E 9 3- BUTYL 2-HYOROXYNAPHTHOPUINONE; 3-I-EUTYL 2-HYOROXYNAPHTHOPUINONE~3-~~-OIMETHYL-Y-CJH-ETHYLl ET HY L A C ET0 AC E T AT E t 3 t 4- ME THY 1 ENE0 I O XY B E NZ AL OIETHYLMALONATEt4-CHLOROBENZAL OIETHYLMALONATEI 2-FLUOROBENZAL 01 ETHYLMALONATE, 4-FLUOROBENZAL 0 1 ETHYLHALONATEI 3-FLUOROBENZAL 0 1 BENZYLAMINE 0 1 BENZYLAMINE 0 1 BENZYLAMINE 0 1 BENZYLAMINE 4-OIHETHYLAM INOBIPHENYL N-(4-OIPHENYLl-ETHYLAMINE N-l4-DIPHENYL)-AMINOETHANOL 2-HYOROXYIMINOOIBENZYL 2-HYOROXYlMlNODI8ENZYL 2-HYOROXYI!4INOOIBENZYL lr+NAPHTHOPUINONEr 2-BUTYLAMINO 1~4-NAPHTHOPUINONE~Z-EUTYLAMINO lr4-NAPHTHOQUINONE~2-AMINO~3-8UTYLTHIO ET HY LCY AN0 AC E T AT E. 214- 0 I THO XY 8 EN2 AL ETHYLCYANOACETATEt 3.4-OIMETHOXYEENZAL ETHYLCYANOACETATEI 3.5-DIMETHOXYEENZAL DIETHYLMALONATEI 2-NITKOBENZAL OIETHYLMALONATEI~-NITRCJ~ENZAL 01 ETHYLMALONATE.3-NITRO8ENZAL AZOBENLENEI 4-OIMETHYLAMINO DIBENZYLPHOSPHORIC ACID OIBENZYLPHOSPHORIC ACID 0 1 BENZYLPHOSPHORIC ACIO OI8ENZYLPHOSPHORIC ACIO 018ENZYLPHOSPHORIC ACID OIBENZYLPHOSPHORIC ACID OIBENZYLPHOSPHORIC ACID G-PHENYLPROPYLPYRIOIN I M BROMIDE U ~~~-NAPHTHOQUINONEI~-EUTYLHYORAZINO 1~4-NAPHTHOQUINONE~2-I-BUTYLHYORAZINO N-SULFANILYL-3v4-XYLAMIOE N- SULF AN I L Y L - 3 4-XYL AM I DE BARBITURIC ACIOi 1-CARBETHOXYMETHYL-5-5-CJIALLYL 3-8ENZOYLMETHIO-4-AMINO-6-I-PR-l~2~4-TRIAZINE-5-ONE ETHYLACETOACETATEI~-METHYL~ENZAL ET HY L I C E TO AC E T A T E, 3-M E THY LEENZ AL ETHYLACETOACETATE. 2-METHYLEENZAL ACETYLACETONE. 29 4-OIMETHOXYBENZYL BENZALMALONATEI DIETHYL ESTER ET HYLACETOACETAT E l 4-METHOXYEENZAL ETHYLACETOACETATEI~-METHOXYBENZAL 1-CYCLOEUTYL-1-ET-3-lM-TRIFLUOROMETHYLPHENYLl-UREA N-CYCLOPENTYLCINNAMAMIOE NI N-PENTAMETHYLENECINNAMAMIOE 6-AZAURIOINE TRIACETATE (PKA=6.35l(NCS 6 7 2 3 9 1 NIN-OIMETHYLTRYPTAMINE. 5-ACETYL METHOHEXITAL PHENOXYACETIC ACID.4-CYCLOHEXYL 2-METHOXY-4-ALLYLPHENOXYACETAMI DE, NIN-01 ME THYL
46
4.79 4.82 -1.56 4.26 -1.78 1.94 3.29 3.35 3.27 0.72
= = = = =
N
77 30
26 62 62
62
=
A A
3.68 3.60
0.68 1.79 3.52 3.28 3.32
304
304 466 141 466 466
3.82
2.77 0.66 0.40 4.69 1.96 3.19 0.42 3.19 3.29 1.51 3.11 2.39 2.43 3.20
316
316
316
466 466 466 141 141 141 304 304 304 304 304 304
2.84 2.59 3.11
B =
2.23
2.50 2.20 2.65
2.26
2.71 2.81 4.58 1.09 0.10 -0.29 1.07 1.97 -1.13 1.81 4.58 2.40 1.50 1.29 1.75 1.85 1.69 -1.86 0.95
302
467 467 467 467 467 467 467 65 457 457 393 393 433 134 304 304 304 304 141 304 304 65 446 446 22 7 448 442 7
=
A A A
7
46
-1.86
0.95 0.87 2.52 2.08
=
A A
62
62
63 63
08 .8
2.52 2.54 2.07
=
N
0.32
2.07
2.35
2.50 2.58 1.00 3.26 1.91 1.93 2.97
2.97
0.82
1.44 -0.20 65
=
A
-0.20
2.84 3.79
0.36
1.81 3.79 1.53
10
142 447 4 16 138 448 448 56 438 438 390 391 370 14 65
=
A
0.01
2.08 1.25
A-BROMO-I-VALERYL-PSEUOOCUMIOINE
P-AMINOSALICYLIC ACID. 7-CHLOROHEPTYL ESTER N-EUTYLNORFENFLURAMINE Nv N-DI ETHYLTRYPTAMINE N-METHYL-N-ETHYLTRYPTAMINE. 5-METHOXY P-HYDROXYBENZOIC ACIOIHEPTYL E S T E R G L U C O P Y R A N O S I O E ~ 3 r 5 - O I M E T H Y L P H E N Y L (BETA1 GLUCOPYRANOSIOE,3-ETHYLPHENYL (BETA1 P-AMINOBENZOIC ACIOIHEPTYL ESTER N-METHYL C A R B A M A T E ~ 3 r 5 - O I - I - P R O P Y L P H E N Y L P-AMINOSALICYLIC ACIOvN-HEPTYL ESTER P-AMINOSALICYLIC AC10.7-HYOROXYHEPTYL ESTER 1-l2-OIMEAHINOET~-3~M-MEOPHENYLl-2-IMIOAZOLIDINONE P - A M I N O P H E N Y L ~ O I E T H Y L A M I N O P R O P Y L KETONE P-AMINOBENZOIC ACIOi A-ME-8-1 OIETAMI-ETHYL ESTER 01 ETAMI ETHYL ESTER P-AMINOBENZOIC ACI 018-ME-8-1 BENZOIC A C I O I P - P R - A M I N O I N ~ N - O I M E T H Y L A M I N D E T H Y L ESTER ESTER BENZOIC ACI0.P-PR-AMINOsNvN-OIMETHYLAMINOETHYL BENZOIC ACIOvP-PR-AMINO~NIN-DI~ETHYLA~INOETHYLAMINOETHYL ESTER BENZOIC ACI0.P-PR-AMINOININ-DIMETHYLAMINOETHYL ESTER N-M-TOLYLCARBAMIC ACIO~DIETHYLAMINOETHYL ESTER N-O-TOLYLCARBAMIC ACIO.OIETHYLAM1NOETHYL ESTER N-P-TOLYLCARBAMIC ACIOIOIETHYLAMINOETHYL ESTER N-M-METHOXYPHENYLCAREAMIC ACIOIOIETAMINOET.ESTER N-0-METHOXYPHENYLCARBAMIC ACID.DIETAM1NOET.ESTER N-P-METHOXYPHENYLCAREAHIC ACIO;OIETAMINOET.ESTER TETRAETHYLAMMONIUM PICRATE L1-OCTYLNICOTINAMIOE CHLORIOE ANIL 1NE.P-I 4-OIETHYLAMINOBUTYLI NeN-DIBUTYL-3-PYRIOYLMETHYLAMINE TETRAOECANOIC ACIO/MYRlSTIC ACID/
1.30
3.95 0.27 0.76 4.83
65
4.83
= =
02 .6
44 14 14 0.31 4.26 2.48 1.42
02 .6 03 .1
4.80
370
468 459 460 460 449 449 449 449
08 .6
17 .6
31
2.44 2.24 2.32 3.15 1.95 2.81 2.25 0.78 0.46 0.75
17 .6
3.01 2.78
28 .6
3.15 2.96 1.62 1.34 1.26 1.42 1.24 -0.14 3-83 1.47
=
A
378
378 378
378
378 378 93 373 459 341
44 44 44 44 44 44 46 31
8 8 16 8 .0
B
03 .6
0.55 0.35 -0.58 -0.14 3.26 1.47 4.28
8 8
= =
60
31
139

EMP I R I AL C FORMULA
NO.
SOLVENT
REF FOOT NOTE 291 409 469 469 4 69 469 410 410 46
LOGP SOLV -1.30 2.90 2.36 2.38 1.87 1.79
LOGP ,OCT -1.30 2.90 2.36 2.38 1.87 1.19 2.91 2.41 1.12 2.61 4.69
NAME TRIBUTYLETHYLAMMONIUM I O D I D E 2- PHENYL- 1t 3- 1NOAN EO ION E
4801 4802 4803 4804 48C5 4806 48Cl 4808 4809 4 8 10 4811 4812 4813 4814 4 0 15 4816 4811 4818 4819 4820 4821 4822 48 23 4824 4825 4826 4827 4828 4829 4830 4831 4832 4833 4834 4835 4836 4837
OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL 0 C T ANOL
= = = =
1.96
0.96 2.47 1.12 3.94 2.61 4.69 1.13
A 2-06 A
218
OCTANOL OCTANOL 469 141 4 63 216 304 411 10 306
= =
=
A
C14H3211N1 C15H1002 C15HllCL1N201 N2 C 1 5 H11C L 1 01 t15HllFlN201 Ci5H12N202 C15H12N202 C15Hl2N202 C15H1201 C15H1202 C15H13CL103Sl C15H13N101 C15H13N102 C15H13N104 C 1 5 H 1 4 I 1N104S1 C15HIQIlN104S1 C15Hl4N2 C15Hl4N402Sl C15H14N402Sl C15H14N40251 C15H14N402Sl ClSHl4N4OZSl C15H14N402S1 Cis~icoz C15H1403 C15H1404 C15 H 1 4 0 4 C15H1405 Cl5H1405 C15H15N1 C15H15N103 C15H168RlN101 C15H16N202 C15H16N202 C15H16N4 C15 H1bN4 t15H16N451 C15H1602S1 C15H1603 C15H1604 C15H1604 C15H1604 C15HllN102 C15n17N102 C15H18BRlhl C15H18N202 C15H1801 C 15H1804 ci5~i804 C15H1804 C15H1804 C15H1805 C15H1805 C15H1805 C15H1806 C15H19N101 C15H19N101 C15H21AL106 C15HZlC0106 C15HZlC0106 C15H21C0106 C15H2 1CR106 C15H21N1 ClSHZlNl C15H21 N l O l . HCL C15HZlNlO2 C15H21N302 C15 H2 1RH 106 C 1 5 H2 2CL 1N103 C15HZZN201 C 15 H2 206 C15H23N102 C15 H2 3N 103 C15H2 3N103 C 15H2 3N 1 0 4 C 15 H23N 1 0 4 C15H23N302 C15H24N202 C15H24N202 C15H24N202 C15H24N202 C15H24N202 C15H24N202 C 1 5 H24N202 C15H24N202 C15H24N202 C15H24NZ02 C 15 H24N203 C15H24N203 C 15H24N203 C15H24N402S2 C 1 5 H24N4 02 S 2 C15H24N40252 C 15 H24 N4O2S 2 C15H25CLlN201 C15H268RlN1 C15H268RlNl Cl5H26N2
INALOL IN-2-ONEe l-ME-~PHENYL-l-CHLORO l-NE-4-PHENYL-6-FLUORO
W INAZOL IN-2-ONEt l-NE-4-PHENYL-b-CHLORO

Q) INAZOL IN-2-ONE.
& INAZOLIN-2-ONE
31 .8
1.99 1.10
3.61 1.99 2.69

1.51 1.93 1.96 1.95 1.83 1.15 2.58 3.46 1.44 1.29 2.84
4838
4839 4840 4841 4842 4843 4844 4845 4846 4847 4848 4849 4850 4851 4852 4853 4854 4855 4856 4857 4858 4859 4860 4861 4862 4863 4864 4865 48 66 4861 4868 4869 4870 4871 4872 4873 48 74 4875 4876 4877 4878 4879 4880 4881 4882 48 e3 48 84 48f5 4886 48 7 4888 4889 4890 4891 4892 4853 4894 4895 4896 4897 4858 4899 4900
CCL4 PARAFFINS OCTANOL CHCL3 CHCL3 BENZENE I-PENT. ACETATE CCL4 OCTANOL DIETHYL ETHER DIETHYL ETHER 01 ETHYL ETHER DIETHYL ETFER DIETHYL ETkER OCTANOL N-HEPI AN E OILS OIEIHYL ETCER CYCLOHEXANE DIETHYL Ell-ER I-BUTANOL CHCL3 CYCLOHEXANE 0 1 ETHYL ETHER DIETHYL ETI'ER DIETHYL E T C E R DIETHYL ETtER PARAFFINS CYCLOHEXANE OCTANOL DIETHYL E T k E R CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CCL4 CHCL3 BENZENE CCL4 CCL4 CHCL3 N-I-EPTANE OCIANOL OLEYL ALCOHOL OCTANOL CCL4 N-HEPTANE CHCL3 OCTANOL OLEYL ALCOHOL N-HtPTANE OLEYL ALCOHOL N-HEPTANE OCTANOL OCTANOL OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOHOL OCTANOL OIETHYL ETtER OILS OILS XYLENE DI-BUTYL ETHER DIETHYL E T t E R DIETHYL ETtER DIETHYL ETkER DIETHYL ETkER CYCLOHEXANE CHCL3 BENZENE EThYL ACETATE OCTANOL OCTANOL OCTANOL DIETHYL Ell-ER
306
439 393 343 393 343 343 343 4 63 143 143 143 465 465 276 370 441 451 141 3 4 455 141 143 143 143 143 63
-0.12
1.83 A
2
63
2 2
2
62
62 62
62 62
14
2.35 1.51 1.41 1.45 0.64 1.94 -0.83 2.58 3.81 1.50 1.33 3.10
=
N N A
=
A
A A
20 .0 2.82 20 .1
0.03 1.19 2.93 0.70 2.04' 1.30 4.70 4.27 1.58 1.65 1.24 -1.07 2.92 -1.87 1.44 2.69
1.87
h
A
2.82
12 .8
62
A 1.11 A 8
1.46
23 .6
3.81 1.51 1.51
A A A A
62 62
62
62
1.21
-1.87 1.39
316
141
283
457 304 304 304 304 304 304 304 304 304 446 446 472 412 472 472 472 396 396 2 83 142 9 472 416 448 438 390 370 473 370 218 276 460 460 4 60 449 461 449 4 62 449 449 378 378 378 378 474 474 474 474
=
A
62
40 .0
1.09
1.80
2.75 2.98 3.49 3.59 1.36 1.39 1.97
5.5-OIPHENYL-2-THIOHYDANTO IN 5.5-OIPHENYLHYOANTOIN HYOANTOIN. 59 5-OIPHENYL W INALOLIN-2-ONE. 6-HYDROXY BE NZ AL ACETOP HENONE 9-CARBOXY-9rlO-OIHYDROANTHRACENE 2-0H-3-CARBDXY-5-ME-BENZTHIO-2'-CL-PHENYL ETHER C I NNAMANILIOE PHENYL HYOROXYLAMI N E t N-C INNAMOYL PHENOXY ACETIC AC 1013-BENLA MIDO N- IP-IOOO8ENLENESULFONYL IPHENYLALANI NE N- (P-IOOOBENZENESULFONYL IPHENYLALANI NE 9-~INO-lt3-DIMETHYLPHENANTHRIDINE SULFAPHENAZOLE SULFAPHENAZOLE SULFAPHENAZOLE SULFAPHENAZOLE SULFAPHENAZOLE SULFAPHENAZOLE A, A-OIPHENYLPROP IONIC ACID 2-HYOROXYNAP~THOOUINONE13-W-DIYETHYLALLYl 2-HYOROXYkAPHTH3PUINO~Er3-lU-OIWEIHYLACETO~YLl ~-HYOROXYNAPHTHOOUINONE~~-~N-ME-M-HYDROXYME-ALLYLI 2-HYOROXYNAPHTHOOUINONEi 3- 13-CARBOWE TdOXYPROPVLI ~-HYORDXYNAPHTHOQUINONEI~-(~-CAR~OXY~UTYL~ 01 BEkZAZOCINE P-AMINOSALICYLIC ACIOvB-PHENYLEIHYL ESTER A-BRORO- I-VAL ERYL-A-h APHTHYLAHINE lr4-NAPHTHOQUINOhE~Z-CYCLOPENTYLHYDRAZINO 1-PHENYL-l-P-TOLUIDINO-2-NITROETkANE NEUTRAL RED BASE NEUTRAL R E O BASE THIOCARBAZONEI 2.2-OIMETHYOIPrlENYL 1.4-NAPHTrlOOU INOhE t 2-METHYL I 3-BUTY L T H I 0 2-HYOROXYNAPHThOOUINONE~3-I-PENTYL 2 - H Y O R O X Y N A P H T H J O U I N O N E ~ 3-1 3-HYDROXYMETHVLBUIYLI ~-HYOROXYNAPHTH)QJINO~EI~-(~-HYDROXY-~-METHYLBU~YLI 2-HYOROXYNAPHTHOQUI~ONE~ 3-1 W-DIMETHYL-C-CH-PROPYL) 3- (N-4-OIPHENYL AM I N 0 I - PROPAhE- 1t 2-01 OL ~~~-NAPHTHOJUINONE~~-MEIHYL~~-BLIYLAM~NO P - 8 l P n E N Y L T R I M E T H Y L A ~ M O N I U M BROMIDE lr4-~APdTdOPUINONE~Z-PEhTYLHYDRAZlhO ACEIYLACETOqE. 2, 49 6-IRIMETHVLBEhZAL DI THY LMALONATE. 3-METHYLBENZAL ETHYLACETOACET ATE, 3.4-OIMETHOXYBENZAL ETHYLACETOACETATEt 2,4-OlMETnOXYBENLAL ETHYLACETOACETATEI 21 3-DIME TtiOXYBENZAL 01 ETHYLMALONATEI 4-YETHOXYBENZAL
01 E T n Y L M A L O N A T E . Z - ~ E T H a X Y B E h L h L
01 ETHYLMALONATtr 3-METHOXYBENZAL OIETHYLMALONATE. 3-METHOXY r4-HYOROXYBENZAL N-CYCLOHEXYLClNNAMAMIOE NI N-HEXAMETHYLENECINNAMAMIOE
17 .6
3.64 2.04 1.54 2.00 3.62 2.04 -1.54 1.99 0.11 2.04 1.42 0.90 0.65 4.78 1.48 3.54 1.01 2.18 2.87 -1.54 2.54 0.17
ALUMINUM-TRI-ACETYLACETONATE
COBALT TKI-ACETYLACETONATE COBALT TRI-ACETYLACETONATE COBALT -TR I - ACETYL ACETONA TE CrlROMIUH-TAL-ACETYLACEIONATE FEhCAYFAMlNE FE hCAHF AM I N E 2-METHYL-5-ET-2'-OH-6~7-8ENZOMORPHAN/NIH#7910/ 4-ALLYLPHENOXY9CETAMIDEININ-DIETHYL PHYSOST I G M I NE RHENIUM-TR-ACETYLACETONATE P-AMINOSALICYL I C ACIOI 8-CHLOROOCTYL E S T E R NIN-01 ETHYLTRVPTAMINEI 5-METHOXY IBETA I GLUCOPYRANOSIOEI 3- ISOPROPYLPHENYL P-AMINOBENZOIC ACIOIOCTYL ESTER ESTER P-AMINOSALICYL I C ACIDIN-OCTYL 4-ET HO X Y BEN20 I C AC I O I 0 I E THY LAM 1NOE TH YL E STE R P-AMINOSALICYLIC ACI0.8-HYOROXYOCTYL ESTER CYCLOHEXIMIDE
8 8
31 31
=
=
14 65 44 14 14
0.65 5.32 4.11 0.55 4.19 3.32
0.55
4.19 2.78 2.66 2.57
= =
3.20
3.11
2 - I O I E T A M I N O M E I - 6 - M E - 7 - N I T R O I E T R A H Y O R O ~ U I N O L I N E /9.6/ P-AM INOBENZOlC ACI O V A t A-DIME-I)- i 01 T A M I -ETHYL ESTEK

ESTER P-AMINOBENZOIC A C I O I A I ~ - O I M E - B - ( O I T A M I - E T H Y L P-AMINOBENZOIC A C I O ~ B ~ B - O I H E ~ 8 - I O I E T A M I E T H E S T E R YL BENZUI C ACID, P-BU- AM I N 0 9 N P N-0 I M E THYLAMI NOE THY L ESTER BENZOIC A C I O ~ P - 8 U - A M I N O ~ N ~ N - O I M E T H Y L A M I N O E T H Y L ESTER B E N Z O I C ACIDv P-8U-AM 1NO.N vN-DIME THYLAMI NOE THYL ESTER BENZOIC A C I 01P - B U - A M l N O , N , N - O I M E T H Y L A H I NOETHYL ESTER BENZOIC A C I D v P - B U - A M I N O e N v N - O I M E T H Y L A M I N O E T H Y L ESTER BEN20 I AC I 01P-BU- AM I NO t N t N- D I ME THY LAM I NOE THY L E S T ER C
3.73
3.04 2.43 2.95
3.73
2.79 3.40 2.44
=
A
A
3.30
44 44 44 44 14 14 14 14 46 53 2.76 0.63 0.78 0.85 0.78 1.49 B 1-62 8
1.68
8
8
B
1.62
1.10 0.89 0.46 -1.53
-0.07
1.56
-1.85 0.88
0.46 -1.53 -0.72 2.55
373 65 65
3
17
-0.72 3.05
= =
8
N-P-ETHOXYPHENYLCARBAMIC ACIOIDIETAMINOET.ESTER THIAMINE PROPYL DISULFIDE TH IAMINE PROPYL 01 SUL F IOE THIAMINE PROPYL DISULFIDE T H l AMINE PROPYL 01SULFIDE N1-NONVLNICOTINAHIOE CHLORIDE B E N Z V L O I M E T H Y L H E X Y L A M M O N I U M BROMIDE DECYLPYRIOINIUM BROMIDE SPARTEINE
604 Chemical Review s, 1971, Vol. 71, No. 6

NO. 4901 49C2 4903 4904 4905 4966 49c7 49C8 4909 4910 4911 49 1 2 4913 49 1 4 4915 49 16 4917 4918 4919 4920 4921 4922 4923 4924 4925 4926 4927 4928 4929 4930 4951 4932 4933 49 34 4935 4936 49 37 4938 4939 4940 4941 4942 4943 4944 4945 4946 4947 4948 4949 4950 4951 4952 4953 4954 4955 4956 4957 4956 4959 4960 4961 4962 4963 4964 4965 4966 4967 49 68 4969 4910 4911 4912 4913 4914 4915 4976 4977 4978 4979 4980 4981 4982 4983 4984 4985 4986 4907 4900 49 89 4990 4991 4992 4993 4994 4995 4996 4997 4998 4999 SOLVENT I-BUTANOL OCTANOL OCTPNOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE OCTANOL OCTANOL CYCLOHEXANE CYCLOHEXANE N-HEPTANE N-HEPTANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTANOL OCTANOL OCTANOL OCTANOL OCTANOL HEXANE OCTANOL DIETHYL ETtER DIETHYL ETCER OCTANOL N-HtPTANE 01 ETHYL ETtER DIETHYL ETHER DIETHYL ETtER OOOECANE N-HEPTANE OCTANOL CYCLOHEXANE CYCLOHEXANE OCTPNOL DIETHYL ETtER I-BUTANOL ETHYL ACETATE N- @UTYL PC ETATE OLEYL ALCOHOL OCTANOL OCTANOL I-E(;T&NOL OCTANOL DIETHYL ETHER OCTANOL HEXANE HEXANE CHCL3 N-HEPTAN E PARAFFINS CYCLOHEXANE I-BUTANOL CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE OCTANOL CYCLOHEXANE CYCLOHEXANE CHCL3 N-CEPTANE OLEYL ALCOHOL B E N 2 NE BENZENE DIETHYL ETHER BENZENE OCTANOL O TANOL C CYCLOHEXANE OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOHOL HIXEO SOLVX1 N-HEPTANE OLEYL ALCOHOL OCTANOL OCTANOL N-H E PTAN E OLEYL ALCOHOL N-HEPTANE OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOHOL OCTANOL OILS XYLENE 01-BUTYL ETHER OCTANOL BENZENE REF FOOT NOlE 4 56 268 304 304 141 141 141 141 141 304 141 141 141 141 141 4 69 141 141 304 443 443 227 304 304
9

EflPIRICAL FORMULA Cl5HZbNZ Cl5H2606 C15H32CLlNl C16H9CL102 C16H9F102 C16 H l O 8 R 1N 1 0 2 C16HlOCLlN102 C16HlOCLlN102 Cl6H1OKlN105Sl C16H10N2 Cl6H1002 C16H1002 C16H1002 C16H1003 ClbH1004Sl C l6 H 1 0 0 4 S 1 ClbHllF3NZOl C16HllN102 C16HllN102 ClbHllN103 C16HllNlSl C 1 6 H 1 1N 1S 1 C16H12N2 ClbHlZN2Ol C16H1201 ClbH13CLlN201 C16H14CLlN301 C16H14N202 ClbH14N203S1 C16Hl401 ClbH15CL 1 0 5 C16H16 ClbHl6N202 C16HlbN202 ClbHlbN205Sl ClbH16N206 C16H1603 C16H1605 C16H1605 ClbHl7CLlNZSl Clbrl17N103 C16H17k10351 Clbrl17N103Sl C16ti18N203 C16H18N204SI ClbH18N204Sl ClbHl8N204Sl C16H18N204S1 C16 H18 N204S1 C16Hl8NZ05 C16H18N205Sl ClbHldN205Sl C16H18N20551 C16H18N402 C16H1803 C16H1806 C16H19CL104 ClbHl9CL105 C16H19N1 C16H19N1 C 16H 19N102 C16Hl9N103 C 16H19N3 0 4 5 1 Cl6H2005 C16 H2006 Cl6H2006 C16H2 1F3N2 C16H21N101 C16H21N101 C I 6 H2 1N 1 0 3 ClbH21N103 C16H2 1N104 ClbH22N102 C16H22N102 C16H22Oll Cl6H23CLlN202 C16H23NlOl.HCL C16H23NlOl.HCL C16 H2 3N 101 C16H23N102 C16H23N103 C16H23N103 C16H23N304 C16H24CLIN103 C16H24N105 C16H2406 C16H2406 C16H25N103 C16H25N103 C16 H25N 104 C16H25N104 C16H25N 105 Cl6H26N202 C1 6 H2 6N202 C16HZbN202 C16H26NZ02 ClbHZbNZOZ ClbH26NZ02 ClbH27CLlN201 C16H32N201 NAME SPARTEINE GLYCEROL, TR I-EUTYR A T E N-OECYLPIPERIOINE HYOROCHLORIOE INOANEt l r J-OIONEI 2 ( 2-CHLORO8ENZALI INOANEI l r 3-OIONE. 21 2-FLUROBENZAL I lr4-NAPHTHOQUINONE~Z-BROHOI3-ANILI" lr4-NAPHTHOPUINONE~ 3-ANILINO-2-CHLORO 11 4-NAPHTHOPUINONEI 2-CHLORO v 3-ANIL I N 0 lr4-NAPHTHOPUINONE~2-ANILINO-3-SULFONATE~K-SALT ~ENZALHALONONITRILEIA-PHENYL INOANE, I ~ ~ - O ~ O N E I Z - ~ E N Z A C l r 4-NAPHTHOPUINONEq 2-PHENYL l r 4-NAPHTHOPUINONE~ 2-PHENYL lr4-NAPHTHOQUINONE~2-PHENYL~3-HYOROXY l r ~-NAPHTHOPUINONEI 2-PHENYLSULFONYL lr4-NAPHTHOPUINONE~2-PHENYLSULFONYL WINAZOLIN-~-ONEI~-HE-~-PHENYL-~-TRIFLUOROHETHYL 1I 4-NAPHTHOPU INON E 1 2- AN I L I NO ~~~-NAPHTHOPUINONEI~-ANILINO COUMARINI~-CARBOXYANILIDE PHENOTHI A2 I N , 39 4-BEN20 PHENOT H I A2 INEI l r 2-BEN LO 5-HETHYL-6H-PYRIO0~4~3-8lCAR8AZOLE (87206I(PKA= 7 - 0 2 ) CYANOACETANILIOEIBENZAL 1-INOANEONEp 2-BENZYL I O I N E DIAZEPAM L I BR IUM W INAZOLIN-2-ONEv 6-HETHOXY W I NA Z OL I N- 2 -0 NE t 1-HE- 4- PHENYL 6- HET H Y L S UL F ONY L OIBENZOCYCLOOCTANE-5-ONE 7-CL-4rb-DIMEO-ba-flEGRIS-2'-EN-3r4'-DIONE CY CLOP H ANE I~~-NAPHTHOPUINONEI 2-CYCLOHEXYLHYORAZINO ~~~-NAPHTHOPUINONEI~-CYCLOPENTYLHETHYLHYORAZINO CEPHALOSPORANIC A C I O ~ 7 - ~ P H A N O E L A H I O O I - O E S P C E T O X Y BISIP-AMINOSALICYLIC A C I D ) ETHYL ESTER 2-HYOROXYNAPHTWQUINONE13-CYCLOHEXYL 2-~OROXYNAPHTHOPUINONE~3-~2-HE-3-CAR8OflETHYOXYPROP 2-HYOROXYNAPHTHOQUINONE~3~~-CAR8OflETHOXY8UTYL~ ETHYL "CHLORPROHAZINE" P- AM INOS AL I CYL I C AC I O v G- PHENYL PROP Y L E STER 2-ACETAflfDO-3-8UTYLTHIO 1.4-NAPHTHOQUINONEv 1~4-NAPHTHOQUINONErZ-ACETAHIO0~3-8UTYLTHIO lr4-NAPHTHOQUINONE~2-ACETAMIOO~3-8UTYLAHINO BENZYLPENICILLIN BENZYLPENIC I L L I N BENZYLPENICILLIN BENZYLPENICILLIN BENZYLPENICILLIN MALONYL UREArETHYL-(2-HEO-4-ALLYLPHENOXYl P E N I C I L L I N I A-HYOROXYEENZYL PHENOXYPENICILLIN/PENlCILLIN V/ PHENOXYPENICILLIN/PENICILLIN V / NIALAflIOE 2-HY OROXYNAPHTHOOUINON E, 3-HE X Y L GLUCOPYRANOSIOEI~-NAPHTHYL (BETA1 ~-CL-~'-OH-~I~-DIHETHOXY-~'~HEGRISAN-~-ONE
LOGP SOLV 2.85 2.54 1.77 3.92
LOGP OCT
3.50
2.54 1.77
07
= =
3.82
2.00 4.22 1.56 -0.99
4.22 -0.99 4.40 2.14 2.69 2.84
= = = = =
3.52 26 26
3.40 4.40
3.62
0.49 2.14
1.50
2.69 2.84
26 .3
0.97 3.23 3.84 4.06 2.11 3.69 2.82 2.44 1.91 0.59 2.58 0.62
4.06 = 2.82
2.44 1.91 0.59 2.58
218
469 469 276 456 276 457 457 56 416 143 465 143 415 370 141 141 141 127 106 130 476 476 142 127 127 130
A A
= = = = = =
A A A
23 .3
62
23 .3
1.57 1.56 -0.28 4.30
62
14 62 62 62
14
12
1.65 1.64 -0.28 1.49 4.76 2.40 2.53 4.45 2.19 2.07 1.28 0.49 1.83 1.93 0.20 1.59 1.60 1.38 1.40 2.09 0.12
2.23
2.34 2.07 1.63 1.82
= =
A
-0.22
1-66 1-60 1.93 1.40 = 2.09 = -0.34 0.87 * 4.41 A 0.76 = 2.64
263
143 438 456 456 396 396 316 304 130 304 304 304 206 446 4 46 405 471 142 137 137
65 62
0.87
4.90 0.76 -0.41
-2.82
31 31 3.35 2.04 -0.58 3.79 -0.23 3.35 2.33
7-CL-4'rb'-OI-OH-4~6-OIHEO-21~HETHYLGRISAN-3-ONE
BENZYLAHPHETAMINE BENZVLAHPHETAHINE NI N-01-8-HY DROXYETHYL-4-AH I N 0 8 I PHE NYL ETHYLCYANOACETATEI~-BUTOXYBENZAL AH P I C I L L I N OIETHYLMALONATE~3-ETHOXY8ENZAL 0 I HY LHALONAT Et 3s 4-0 I ME THOXYB E NZA L ET DIETHYLMALONATEI 3.5-DIHETHOXYEENZAL BENZIH IOAZOLEr 5-OCTYL-2-( TRIFLUOROHE THYL I N-CYCLOHEPTYLCINNANAMIOE N.N-HEPTAt4ETHYLENECINNAHAMIOE HOHATROP I N E HOflATROPINE 2-HETHOXY-4-ALLYLPHENOXYACETYLMORPHOLl" 2-ME-5-PH-5-CARBETHOXY-2-AZAEICYC( 2 I 21 1lHEPTANE/EXO/ 2-HE-5-PH-5-CAR8ETHOXY-2-AZAEICYC~2~2~llHEPTANE/ENOO/ GLUCOSE PENTA- A t E TA TE 2-ALLYLOXYL-4-CL-N~Z-O1ETAHINOET)-BENZAMIOE 2r 9-01 METHYL-5-ET-2'-OH-6~ 7-8ENZOHORPHAN/hIH17938 2~5~OIHETHYL~9~ET-2'~O~~6~7~8ENZOHORP~AN/hIH#795l N-HEPTYLCINNAHAM IOE 2 - H E T H O X Y - 4 - A L L Y L P H E N O X Y A C E T A H I O E ~ N-HE-N-PROPYL 2-HETHOXY-4-ALLYLPrlEkOXYACETAHIOE~N~N-OIETHYL 2-HETrlOXV-b-ALLYLPHENOXYACETAHIOE~~~N-OIETrlYL 8ARBITURIC A C I O ~ 1 - ~ N ~ N - O I E T - C A R 8 A M V L f l E l - 5 ~ S - O I A L L Y L P-AMINOSALICYLIC ACIO*9-CHLORONOhYL ESTER 2 - H E T r l O X Y - 4 - E T H O X Y C A R B O h Y L P H E N O X Y A C E T A H I O E 1N.N-01 E T GLUCOPYRANOS 1 DE. 2- I SOPROP YL- 5-MEPHEkYL I 8 E T A I GLUCOPYRANOSIOE.3T-EUTVLPHENYL (BETA) P-AMINOSALICYLIC ACIDIN-NONYL ESTER 2-METHOXY-4-PROPYLPHENOXYACETAHIOE~N~N-OIETHVL P-AHIFtOSALICYLIC ACIOI~-HYOROXYNONYL ESTER 3-HEO-4-ETO-8ENZOIC ACIO~OIETHYLAflINOETHYLESTER 3 ~ 4 . 5 - T R I H E T ~ X Y 8 E N Z O I C ACIOiOIETHYLAHINOETHYL ESTER P-AHINO8ENZOIC A C I O ~ A ~ A ~ 8 - T R I M E - 8 - ~ O I E T A M I - E T H Y L EST. EST. P-AMINOBENZOIC A C I D . A . B . B - T R l M E - B - I O I E T A H I - E T H Y L BENZOIC AC IO, P-AMYL AH IhO r N r N-01MEAHl NOEThYL ESTER BENZOIC A C I 0 . P - A H Y L A M I N O I N ~ N - O I H E A H I N O E T H V L ESTER BENZOIC ACID.P-AMYLANINO~k.N-DIMEAMINOE1HVL ESTER BENZOIC ACIO; P-AWL AMINO 9N.N-01 MEPMINOETHYL ESTER N1-OECYLNICOTINAHIOE CHLORIOE PdPERIDINE~l-DECYL~3CAR8AMVL
-0.83
3.22
4.38 2.04 2.46 2.86 -3.00 4.36 2.21 1.75 2.81 2.81 1.17 2.07 -1.31 -1.52 2.01 3.05 2.37 1.01 1.07 3.24
=
8
31
1.20
1.46 1.46 1.21 2.19 -1.31 -1.52 2.72 1.46 2.51 1.82 2.28 1.48
3
405 283 2 83 446 142 142 142
31
= =
433
416 142 436 438 37 0 142 3 70 473 473 460 460 449 449 449 449 373 476 14
0.55
14 1.07 1.01 1.76 2.70
1.01 =
14
1.15
2.81 2.39 3.43 3.48 4.14 2.79 3.92 3.33 1.12 -1.52
3.38
2.96 3.96 4.04 4.14 3.72 1.12 -0.51
=
A
5000
=
8
NO. 5001 5002 5003 5004 5005 5006 50C7 5008 5009 5010 5011 5012 5013 5014 5015 5016 5017 5018 5019 5020 5021 5022 5023 5024 5025 5026 5027 5028 5029 5030 5031 5032 5033 5034 5035 5036 5037 5038 5039 5040 5041 5042 5043 5044 5045 5046 5047 5048 5049 5050 5051 5052 5053 5054 5055 5056 5057 5058 5059 5060 5061 5002 50C3 50t4 5065 5066 5067 5068 5069 5070 5071 5072 5073 5074 5075 5076 5077 5078 5079 5080 5C81 5082 5013 5084 50 1 5 5086 5087 5088 5089 5090 5091 5052 5093 5094 5055 5096 5097 5098 5099 5100
SOLVENI N-HEPTANE OIETHVL ETHER ME-1-BUT.KETONE BENZENE CCL4 NITROBENZENE OCTANOL CYCLOHEXANE CVCLOHEXANE CYCLOHEXANE OIETHVL ETliER CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE PRIM. PENTANOLS DIETHYL ETHER HEXANE HEXANE OCTANOL HEXANE N-HEPTANE DIETHYL ETHER O I E T H K Ell-ER HEXANE CHCL3 OOOECANE OCTANOL OCTANOL OCTANOL OCTANOL CVCLOHEXANE CHCL3 CHCL3 N-HEPTANE OOOECANE OCTANOL CHCL3 OCTANOL OCTANOL OOOECANE OOCECANE OCTANOL OCTANOL DIETHYL E T k E R I-BUTANOL CHCL3 HEXANE DIETHYL ETkER DIETHYL E T k E R N-HEPTANE OCTANOL I-BUTANOL OCTANOL OCTANOL CHCL3 CHCL3 N-I-EPTANE DOCECANE CYCLOHEXANE CHCL3 CHCL3 DIETHYL ETkER N-BUTANOL I-BUTANOL PRIM. PENTANOLS HEXPNOL CYCLOHEXANOL PARAFFINS DIETHYL ETkER DIETHYL ETCER OCTANOL CHCL3 CHCL3 N-I'EPTANE OCTANOL OCTANOL OCTPNOL N-kEPTANE DIETHYL E T k E R OILS I-BUTANOL N-tEPTANE DIETHYL ETkER CYCLOHEXANE CYCLOHEXANE CYCLOHEXINE OCTANOL DCTPNOL DIETHYL ETkER I-BUTANOL 01-I-PR. ETkER N-I'EPTANE OLEYL ALCOHOL OCTANOL OLEYL ALCOHOL N-FEPTANE CHCL3 CHCL3 CYCLOHEXANE OLEYL ALCOHOL
REF FOOT NOTE 479 236 236 480 480 92 268 141 31 17 17 46
LOGP SOLV 5.31 2.88
LOGP OCT
EWPIRXCAL FORMULA C16H3202 ClbH3404P1 C16H3 5 0 4 P 1 A C 16H35 0 4 P 1 Cl6H3504Pl C16H36IlNl = Cl6H3BBR2NZ Cl7H12CLlN102 C17H1202 Cl7H1202 A Cl7H1203 C17H1203 C17H13N102 CllHl3N102 C17H14N202 A Cl7H1403SI C17Hl7CL106 Cl7Hl7CL106 C17Hl7CL106 ClTH17CL106 C17HlBN206 A C17H1803 A C17H1805 Cl7H1806 N C17H19CLlN201Sl C17H19CLlN20lSl = C 1 7 H 1 9 C L l N 2 0 1 S I .HCL = CITHI9CLlNZSl = ClIH19CLlN2Sl = C17H19CLlN2SI C17Hl9CLlN2Sl N C17H19CLlNZSl N Cl7Hl9CLlN2Sl ClIH19CLlNZSl C17H19CLlN251 = C17H19CLlNZSl.HCL N C17H19CLlN2Sl.HCL = tl7H19CLlNZSl.HCL = C17H19CLlN2Sl.HCL CIIH19CLlNZSl C17H19CLlN251 C17H19N103 = C17H19N103 8 C17H19N103 C17H19N103 8 C17HZON2 Cl7H2ONZ A C17H20N202 A C17H20N202 C17HZON202 = C17HZON205Sl C17H20NZ05Sl = C17H20N20651 = CllHZONZSl N C17H2ONZSl N C17H20N2S1 C17H20 N2S 1 ClTHZONZSi Cl7H2ON2Sl N C17HZONZS1 N C17HZON2Sl C17HZON406 C17H2ON406 C17H20N406 Cl7HZON406 C17HZON406 C17HZON406 C17 HZON406 A C17H2003 A C17H2004 = C17H21CLlNZSl N C17H21CLlNZSl 8 C17HZlNl C17 HZ 1N 1 = C17H21N101 = C17HZlN101 = C17HZlN101 C17HZlN101 8 C17H21N104 8 C17H21N104 C17H21N104 C17HZlN104 A C17HZZhZ02 C17H2205 C 17HZ 3N101 C17H23h101 = C 17 rl2 3N I C 3 = C17HZ 3 N l C 3 B C17H23N103 C 1 7 H23N 1C3 Cl7H23N103 C17 h 2 3 h 1 0 3 C17H23N103 = C17H23N301 C 17h23N302 C17h24NZ02 B C17 r(2 5C L 1h Z O l . HER 8 C 1 7 H 2 5 C L l N 2 0 1 .HBR C17H25NlCl C17H25N103
N&ME HEXAOECANOIC A C I O I P A L M I T I C ACXDI DIOCTVLPHOSPHATE DIOCTVLPHOSPHATE PHOSPI~ORIC ACIDvDIlZ-ETHVLHEXVLI PriOSPHDRIC A C I D ~ O I l 2 - E T H V L H E X V L l TETRA-IN-BUTVLI AMMONIUM IODIDE OECAMETHONIUM BROM I DE 1 ~-NAPHTHOPUINONEI~-CL s 3 - A N I L I N O s 6-METHYL , XNOANEs l r 3-0IONEs212-METHVLBENZAL) 1.4-NAPHTHOQUXNONEs 2-METHVLv 3-PHENVL
20 .3
0.11 0.09
0.07 -1.00 4.22
1.81 1.51 -1.00
304
141 143 304 141 141 481 143 4 56 4 56 62
38 .3
3.52 3.16 3.44 3.05 4.22 2.34 4.35 0.14 -0.10 2.18 2.89
2-HYMIOXVNAPHTt#JOPUINONEs3-PHENVLMETHVL INOANE~ls3~OIONEs2l2~METHOXVBENZALl 1~4-NAPHTHOQUINONEs2-ANILINO~6-NETHVL

1.4-NAPHTHOOU INONE * 2-METHVL 3-ANIL I N 0 S~PVRAZDLONE~ 1-PHENYL, 3-METHVLsCBENZOVL 2-HVOROXVNAPHTHOQUINONE, 3-1 W-A-THI ENVLPROPVL I 7-U-4~6~4'-TRIMEO-6'-MEGRIS-3~-EN-3rZ'-OIONE
2.62
62
3.93
2.18 4.44
2 38
4 56 416 14 1 4 3 62 465 62 4 56 482 68 475 475 46 483 4 4 218 56 484 68 482 482 * 6 9 485 14 475 475 46
02 .6
1.62 4.93
OO-7~CL~4s6~2'~TRIMEO~6'-MEGRIS-2'~EN-3~4~~OIONE
G ISEOFULVXN R LO-7~CL~4ibr2'~TRIMEO~6'-MEGRIS~2'~EN~3s4'~OIONE BISIP-AMINOSALICYLIC A C I D ) PROPYL E S T E R 2-HVOROXVNAPHTl+3PUINONEs 3-CVCLOHEXVLMETHVL 2-HYOROXVNAPHTl+34UINONE~3- LCCAR8OMETHOXVPENTVL) 4~6~2'-TRIMEO-6'-MEGRIS-2'-EN-3r4'D10NE CHLORPROMAZINE SULFOXIDE
37 .0
-0.44 -1.05 -0.12 -0.66 5.16 5.35 5.32 0.95 1.09 2.10 1.86 4.86 1.51 1.22 1.23 1.79 4.79 4.67 0.76 0.70 -0.68 0.87 4.04 2.38 2.03 2.13 -1.70
33 .6
-0.37 -0.66 5.16 5.35 5.32 1.62 2.55 1.51 1.73 1.23 1.79 0.76 0.70 0.25 0.72
CHLORPROMAZINE-SULFOXIOE
CHLORPROMAZINE-SULFOXI0E.HCL CHLORPROMAZINE CHLORPROMAZ I N E CHLORPROMAZINE CrlLORPROMAZIkE CHLORPROMAZINE CHLORPROMAZINE CHLORPROMAZINE CHLORPROMAZINE CHLORPROMAZINE HYOROCHLORIOE CHLORPROMAZINE HVOROCnLORIOE 1-CHLORPROMAZIhE IiYOROCHLORIOE 3-CHLORPROMAZINE HVDROChLORIOE 1-CHLORPROMAZINE 3-CHLORPROMAZ INE MORPHINE MORPHIhE MORPH1NE WO RPhI NE OESOIHETHYLlHIPRAMIYE OESOIMETHVL IHIPRAM I N l~4-NAPHThOPUIhONE~2-CYCLOHEXVLMETHVLHVORAZI~O 1 9 ~-NAPHTHOPUINONEI 2 - U - C V C L O P E h T V L E T H V L H V D R A Z I N O TROPIC ACIDvk-ET-h-G-PICOLYLAMIOE P E N I C I L L I N . A-PliENOXYEThVL PEhICILLIN.A-PHENOXYETnVL
486
475 475 475 475 186 2 18 3
46
46
46
17
4
466 466 457 457
677 ...
3.22
1.89 1.99 2.28 0.14 1.22 4.55 1-16 1.94
62
62
127 130 127 483 482 482 485 475 484 482 482 487 487 487 487 487 487 487 143 465 475 486 396
2.28
44 68 69 14
,
0.46 1.22 4.55 0.59 1.43 1.71 4.02 1.50
PEhlCILLIN~2~6-OlMETHOXVPHENVL
PROMAZINE PRCMALINE PROMAZINE PROMAZINE PROMAZINE PROMETHAZINE PROMETHAZINE PROMETHAZINE RIBOFLAVIN RIBOFLAVIN R 1 BOFLAVIN R I BOFL A V I N RI BOFL A V I N R I ~ O F LA V IN RIBOFLAVIN 2-HVOROXVNAPHTHOQUINON E. 3- I-HEPTYL 2-HVOROXYNAPHTHOPUINONE~3-( 5-OH-5-METHYLHEXYLI PROMAZINE HYDROCHLORIOE PROMAZINE HYOROCHLORIOE BENZPHETAMINE BEN2 PHET AM I NE BENAORVL /PKA= 8.98/ OIPHENHVORAMINE 01 PHENHVDRAHINE 01 PHENHYORAHINE COCAINE COCAINE COCA I N E SCOPOLAMINE 1~4-NAPHTHOPUINONE~2-HEPTYLHVORAZINO DI ETHY LM ALON AT E I 3- PROPOXY6ENZAL N-CVCLOOCTYLCINNAMAMIOE NIN-OCTAMETHYLENECINNAMAMIOE AT ROP I NE ATROPINE AT ROP 1NE ATROPINE AT ROP I N E ATROPINE 2-HETHOXY-4-ALLYLPHENO XVACETVLP I PERIOINE MEPYRAMINE I PKA = 8.85/ CINCHONINAMIOE~N~~Z-OIETHYL~AMINOETHVLI-2-METHOXY ATURBAN l-lM-CLBENZVLl-3-N-OIETCARBAMOVLlPIPER1OIN 1- IP-CL BENZYL I-3-N-0 I E TCARBAMOVL I P I PER1 0 I N N-OCTY LC INNAH AM I D E
68
-1.22
1.76 -3.80 -0.17 -0.33 -0.77
69
-0.53 2.25 -0.75 -0.97 -1.28 -1.25 -1.46 5.06 2.09 0.91 1.25 2.47
-0.92 62
62 46 -0.27 -4.70 5.65
2.24
0.91 0.73 3.15
46
31
3.30
3.27 3.40 3 462
4
17
477 457 304
62
2.14 2.33 2.03 -2.36 2.86
2.73 1.92 2.34
2.63
4.00
2.48 3.11 1.79 1.83 0.61 1.94 -0.03 -3.25 2.20 2.85 2.15 -2.89 0.33 1.79 1.83 1.39
446
446 218 218 3 4 488 477 142 276 489 477
17
I2
2.22
2.74 2.85 2.70
27 17 17
490
490
0.40
3.21 2.97
0.05 0.11
3.51
446
142

LOGP OCT 3.29 EMPIRICAL FORMULA C17H25N103 C17H25N107S 1 C17H25N303.HBR C17H25N303.HBR C17H26CLlN103 Cl7H26N201.H8R C1 7 H2 6 N4 035 2 ClfH26N403! C17H2bN403S2 C17H27N104 C17H27N104 C17H27N104 C17H28N202 C17H28N203 C17H28N203 C17H28N203 C17H29N106Sl C17H308RlNl C17H30BRlNl C17H31N102 C17H34N201 Cl7H3811Nl Cl B H l 2 C U l N 2 0 2 C18H12CUlN203 C18H14N203 C18H14N203 C18H1403 C18H15BR103Sl C18H15BRlSl Cl8H15CLlSl C18H15I 1 0 3 5 1 C18H1511S1 C18H15N102Sl C 18 H I 5 N 1035 1 C18Hl501Pl C18H17CR104Sl Cl8HllCR104Sl Cl8H1704PlSl Cl8H18N207Sl Cl8H19CL106 C18H19CL106 C18H19F3NZSl C18H19F3NZSl ClBH19F3N251 ClBH19F3N2Sl C18H19F3NZSl C18H19N304 C18H2OCLlF3N2Sl C18H2OCLlF3N2Sl Cl8H20N203 ClbH2ON206 ClBH2ON2Sl C18H2ON2S1 Cl8H2ON2Sl ClBH2ON2S1 C18H2002 Cl8H2003 C18H200351 C18H2004 ClBH2005 Cl8H2005 C 1 8 H2 1C L l N 2 S 1 Cl8H2lN103 C18H2lN103 C18H2lN103 ClBH21NlO3 C18H21N103 ClBH21N103 C18H21N103 C l 8 H2 I N 1 0 3 Cl8H2lNlO3 C18H2IN104 C 18H2 1N3 C18H22CLlN2Sl C18H22N2 Cl8H22N2 C18H22N2 C18 H22N2 C18H22N201 C18H22N201 ClBH22N201 ClBH22N201 C18H22N201S1 C18H2LN2OlS 1 C18H22N201Sl Cl8H22NZOlSl ClBH22N202S2 C18H22N205Sl C18H22N205Sl C18H22N205Sl C18H22N2S1 C18H22N2S2 ClBH22NZS2 C18H2202S2 C18H2204 Cl8H2204 NAME
NO. 5101 5102 5103 5104 5105 5106 51C7 5108 5 109 5110 5111 5112 5113 5 114 5115 5116 5117 5 1 18 5119 5120 5121 5122 5123 5124 5125 5126 5127 5128 5129 5130 5131 5132 5133 5134 5135 5136 5137 5138 5139 5140 5141 5142 5143 5144 S145 5146 5147 5148 5149 5150 5151 5152 5153 5154 5155 5156 5157 5158 5159 5160 5161 5102 51C 3 51t4 5165 5166 5167 5168 5169 5110 5111 5112 5173 5114 5175 5176 5177 5178 5179 5180 5181 5182 5ie3 5184 5185 5186 5187 5188 5189 5190 5191 5192 5193 5154 5155 5196 5197 5198 5199 5200
SOLVENT OLEYL ALCOHOL CHCL3 CHCL3 CHCL 3 N-PEPTANE CHCL3 MIXEO S O L V I l CYCLOHEXANE CHCL3 BENZENE ETHYL ACETATE N-HEPTANE OLEYL ALCOHOL N-HEPTANE OLEYL ALCOHOL OLEYL ALCOHOL OLEYL ALCOHOL 01 ETHYL ETFER OIETHYL ETPER DIETHYL ETPER CHCL3 OCTANOL OCTPNOL OCTANOL BENZENE DCTANOL CCL4 CHCL3 OCTANOL CYCLOHEXANE O I E T H Y L ETtER CHCL3 CHCL3 CHCL3 CHCLJ CHCL3 CHCL3 CHCL3 OCTANOL CHCL3 CHCL3 CHCL3 OCTANOL HEXANE HEXANE OCTANOL CHCL3 CHCL3 N-HEPTANE OOOECANE MIXED S O L V I 1 OCTANOL CHCL3 MIXED S O L V l l N-FEPTANE CHCL3 CHCL3 CHCL3 CHCL3 OCTANOL DIETHYL TI-ER OCTANOL OCTANOL DIETHYL ETPER OIETHYL ETtER OOOECANE DIETHYL ETkER D I ETHYL ETHER DIETHYL ETI-ER CHCL3 CHCL3 I-BUTANOL CCL4 CL CP2CH2CL ETHYL OLEATE EThYL OLEATE CYCLOHEXANE OCTANOL OCTANOL OIETHYL ETI-ER CHCL3 HEXANE CHCL3 DIETHYL TI-ER CHCL3 HEXANE OCTANOL N-bEPTANE CHCL3 CHCL3 OCTANOL OCTANOL OCTANOL I-BUTANOL CHCL3 CHCL3 CHCL3 CYCLOHEXANE DIETHYL ETtER ETPYL ACETATE
REF FOOT NOTE 142 49 1 490 490 416 490 433 474 474 474 474 370 473 370 473 473 4 60 378 378 378 464 65 65 348 478 297 412 412 141 141 143 96 96 96 96 96 96 96 56 96 96 96 56 456 456 483 482 482 485 475 433 4 15 486 433 416 482 482 482 4 82 2 18 143 276 276 465 143 475 492 3 3 59 493 3 59 4 492 492 494 494 495 56 483 466 466 466 466 466 466 466 483 485 482 482 56 127 127 130 482 482 4 82 141 496 496 46 17 17 14 17 14 14 14 14 14 14
LOGP SOLV 2.75 -1.62 -0.12
0.00
1.68 -0.02 2.23 -0.77 1.17 -2.52 0.07
-0.12 -0.23 -0.25
8
B
2.08
4.27 1.24 3.52 3.37 3.29 1.10 1.09 1.07 2.70 -0.29 4.09 3.90 3.82 1.90 1.89 2.00 -0.29 0.44 1.28 -0.25 -0.22 1.73 3.68
44 44 44 46 46 46 46
8
B
0.44
1.28 -1.15 -0.22
= =
B
= =
A
2-UETHOXY-4-ALLVLPHENOXYPROPIONAHIOE~N~N-DIETHYL ATROPINE SULFATE l-lM-NO2BENZYL I - 3 - I N - D I E T C A R B A M O Y L I P I P E R I O I N E 1- IP-NOLBENZYL 1-3- I N - 0 1 ETCARBAMOVL I P I P E R I O I NE P-AH INDSAL ICVL I C ACID, 10-CHLOROOECYL E S T E R 1-BENZYL-3-( NIN-DI ETCARBAMOYLI PIPER101 NE-HBR BARBITURIC ACID. l-N-HEPTYL-5r5-OIALLYL THIAMINE TETRAHVDROFURFURYL DISULFIDE THIAMINE TETRAHYOROFURFURYL DISULFIOE THIAMINE TETRAHYOROFURFURYL DISULFIDE T H I AM I NE T ETRAHYDRDFUR F URY L 01 SULF IO P-AMINOSALICYLIC ACIDS OECYL ESTER 4-BUTOXY BENZOI C AC 101D IETHYLAM I NDE THYL E STER P-AMINDSAL ICYL I C AC 101 10-HYDROXYOECYL ESTER 2.4-OIETHOXYBENZOIC ACIOIOIETHVLAMINOETHYL ESTER 3 9 4-OIETHOXYBENZOIC AC IO, D I E THYLAMINOETHYL E S T E R P-AMINOBENZOIC A C I O I T E T R A M E - ~ - I O I E T A M I - E T H Y L ESTER N-M-BUTOXYPHENYLCARBAMIC ACIDIUIETAMINOET.ESTER N-0-BUTDXYPHENYLCARBAMIC ACIOIOIETAMINOET.ESTER N-P-BUTOXYPHENYLCARBAMIC ACIOIOIETAMINOET.ESTER N-ME-3-METHOXYCAREONYLPYRIOlNIUM NONYLSULFATE BENZYLOIMETHYLOCTYLAMMONIUM B R O M I D E OODECYLPYRlOINIUM B R O M I D E N-WOECANOYLCYCLOBUTANECAR8OXAMIOE P I PER1 OINEt 1-DECYL t 3-1 N-METHYLCARBAMYLI TRIPENTVL-ETHYL-AMMONIUM IOOIOE
20 .5
3.48 1.73 -0.11 4.04 -0.42 -0.25 -0.63 -2.52 1.12 -1.00 -0.29 2.87
8-PUINOLINOLOIEISI-CUI111 8-PUINOLINOLOlBIS)-CUl1 I I
~ ~ ~ - N A P H T H O P U I N O N E2-ACETAMIOD-3-ANILINO I lr4-NAPHTHOPUINONE~2-ACETAM100~3-ANILINO 2-HYDROXYNAPHTHOPUINONEI3-(W-PHENYLETHYLl TRIPHENYLSULFONIUM BROMATE TRIPHENYLSULFONIUM B R O M I D E TRIPHENYLSULFONIUM CHLORIDE TRIPHENYLSULFONIUM IODATE T R I PHENYL SUL FON IUM I O 0 1DE TRIPHENYLSULFON IUM N I T R I T E TRIPHENYLSULFONIUM NITRATE PHOSPHINE OXIOEv TRIPHENYL TRIPHENYLSULFONIUM CHROMATE TRIPHENYLSULFONIUM CHROMATE T R IPHENYLSUL FON IUH PHOSPHATE CEPHALOSPORANIC ACIO~7(O-MANDELAMIOOl 7-CL-2'-ETO-4~6-01MEO-b'-MEGRIS-2"-3r4'-01ONE 7-CL-4'-ETO-4~6-OIMEO-b'-MEGRIS-3'-EN-3~2'-OIONE TRIFLUPROMAZINE TRIFLUPROMAZINE TRIFLUPROMAZINE TR IFLUPROHAZINE T R IFLUPROMAZINE BARBITURIC A C I O ~ 1 - ~ N - P H E N Y L C A R B A M Y L H E l - 5 ~ 5 - 0 1 A L L Y L TR IFLJPROHAZ I ' . dYOaOCI1LOR I OE TR IFLJPR3YAZIhE nYJ2OCnLOtl I O 6ARt)lTL)RIC A C I O ~ l - B - P d E V Y L E T d Y L - 5 1 5 - D I P L L Y L E I S ( P - A Y I h J S A L I C V L I C A C I O l EJTYL ESTEZ CETriOILILI%E METHOILAZINE PYRAT H I A Z I NE PYRATHlAZINE 4r 4' -STILBENEOIOLI A, A'-DIETHYL 2-HYOROXYNAPHTPOPUINONE.3-(W-tYCLOHEXYLETHYLl 2-OH-3-CARBOXY-5-ME-8ENZTHIO-21-I-PROPYLPHENYLETHER 2-OH-3-CAREOXY-5-ME-8ENZYL-2'-I-PROPYLPHENYLETHER 2-HYDROXYNAPHTHOPUINONE13-(2-ME-5-CAR8OHETHOXYPENTl 2-HYOROXYNAPHTHOQUINONEI3-~W-HE-W-tAR8OMETHOXYPENTl BUTYL "CHLORPROMAZINE" CODEINE CODEINE CDUE INE COOEINE COOE INE CODEINE COOEINE CODEINE OICOOIDE /OIHYOROCOOIENONE/ EUCOOAL /OXVCOOONE/ BEN2 IH I CAZOL E. 1-OIMETHYLAM INOETHVLI 2-BENZYL N-METHYLCHLORPROMAZINE CHLORIDE DESIPRAMINE O E S I PRAM INE OESIPKAMINE DES I PRAM INE LO-HYOROXYOES I M I PRAM INE 2-HVOROXYDESIPRAMINE 2-HYOROXYOESIPRAMINE 2-HYOROXYOES IPRAHINE METHOPROHAZINE METHOPROMAZINE HETHOXYPROHAZINE HETHOXYPROMAZINE PHENOT H I A2 I N . 2-ME SULF ONYL- 10- I 3-01 HE A M I NOPROPYL I PENICILLINgl-PHENOXYPROPYL/PROPICILLIN/ PENICILLIN,2-PHENOXY-2-PROPYL PENICILLIN~l-PHENOXYPROPYL/PROPICILLlN/ TRIMEPRAZINE TH IOHETHYLPROHAZINE THIOHETHYLPROMAZ I N
1~4-NAPHTHOPUINONE~2,3-DIBUTYLTHIO
62
2.87
32 33
1.01
-0.15 -1.00 -0.89 0.36 0.57 5.19 1-30 1.76 1.15 5.14 0.30 1.78 1.46 2.36 1.74 -0.89 5.19 1.82 2.25
44 68 69 14 46 46 14 68 69
68
=
N N
1.78 1.92 1.43 2.40 1.67 2.36 5.07 5.06 4.36 4.91 3.10 3.47
=
N N N N N
0.88
1.92 1.14
69 62 62 62 17 17
1.w
5.07 5.64 4.36 4.91 3.40 3.82 5.07 0.19 -0.10 0.03 1.94 2.17 1.21 -0.62 -1.32 1.29 1.37 0.78 -0.15 4.28 2.88 3.82 2.27 2.43 2.00 1.99 0.72 4.90 1.51 0.71 1.38 3.50 2.65 2.76 0.66 1-06 1.14 1.88 3.45
=
A
=
=
A A B B B E B
1.01
0.78
0.88
1.42 1.63 1.19
44
-0.15 4.28 2.65 3.05 1.84 1.87 1.48 4.90 1.27 1.90 3.50 2.65 2.76 0.42 1.60 1.67 2.36 -0.04 0.75
=
A
8
B A 8
44 14 68 69
=
N N
=
=
=
N N N
A
12 68 68 69
-0.18
0.75
6-OXOESTRIOL 6- OXOEST R I OL
NO. 5201 5202 5203 52C4 5205 52C6 52C7 5208 5209 52 10 5211 52 12 52 13 52 1 4 5215 5216 52 1 7 5218 52 19 5220 5221 5222 5223 5224 5225 5226 5227 5228 5229 5230 522 1 5232 5233 5234 5235 5236 5237 5238 5239 5240 5241 5242 5243 5244 5245 5246 5247 5248 5249 5250 5251 5252 5253 5254 5255 5256 5257 5258 5259 5260 526 1 5262 526 3 5264 5265 5266 5267 5268 5269 5270 5271 5272 5273 5274 5 2 15 5276 5217 5278 5279 5280 5281 5282 5283 5284 525 5286 5287 5288 52 8 9 5290 5291 5292 5293 5294 5295 5296 5297 5298 5299 5300
SOLVENT CHCL3 N-HEPTANE CYCLOHEXANE OLEYL ALCOHOL DIETHYL ETIER E T I Y L ACETATE DIETHYL ETIER EdhYL ACETAIE CYCLOHEXANE CHCL3 OLEYL ALCOHOL CHCL3 CHCL3 CHCL3 N-FEPTANE CYCLOHEXANE N-IEPTANE OLEYL ALCOI-OL OLEYL ALCOHOL OLEYL ALCOHCL CHCL3 CHCL3 CHCL3 CHCL3 I -0CTANOL I-OCTANOL OCTANE CHCL3 CHCL3 N-tEPTANE N-FEPTANE BENZENE BENZENE N - t EPTANE CHCL3 PARAFFINS PARAFFINS DIETHYL ETHER I-BUTANOL I -BUTANOL I-BUTANOL OCTANOL DIETHYL ETtER HEXANE HEXANE HEXANE CHCL3 CHCL3
REF FOOT NOTE 486 4 77 141 142 496 496 4 96 496 304 497 489 497 497 497 498 446 477 142 142 142 490 490 490 490 353 46
LOGP SOLV 0.97 1.49 3.44 2.57 0.89 1.38 -0. Y2 -0.05 3.62 3.67 2.56 2.55 1.77 3.11 -0.07 3.17
LOGP OC T 1.46 3.14 C.90 1.43 -0.69 -0.09 2.91 3.10 N
EMPIRICAL FORMULA C18H23CLlN20lSl C18H23N101 C18H23N10251 C18H23N103 C18H2403 C18H2403 C 18 H2404 C 1 8H 2 4 0 4 C18H2405 C18H25N101 C18H25N302 C18H268RlNlDl Cl8H26CLlN101 C18H2611N101 C18H2602 C18H27N101 C18H27N102 C18H27N103 Cl8H27N104 C18H27N105 C 1 8 H28N201. H8 R Cl8H28N201.HBR C18H28N202.HBR C18H28N202.HBR Cl8H29KlC3S1 C18H29NA103Sl Cl8H30D3 C18H3 l N l O 6 S 1 ClBH31N106Sl C18H3.202 C18H3402 C18H36N201 C18H36N201 C18H3602 C19H15NlSZ C19H16N2 C19Hl6N2 C19H1603 C19H17CLZN305Sl C 19H18 C L 1N3 0 5 s 1 Cl9H19N305Sl C19H2ON203 C1'
NAME METHOXYPROMAZINE HYOROCHLORIOE ORPHENAOR INE 1~4-NhPHTHOOUINDNE~2-8UTYLAMINOI3-BVTYLTHIO 2-METHOXY-4-ALLYLPHENOXYACETAMIOE~N~N-OIALLYL ESTRIOL ESTRIOL 6- A-HY UROXY ESTR IDL 6-A-HYOROXYESTRIOL 01 ETHYLHALONATE, 3-BUTOXYBENZAL OEXTROMETHORPHAN C I NCHDNlNAM 1OE.N-I 2 - 0 1 ETHYL-AMI NOE THYL I-2-ETHOXY OEXTROMETHORPHAN HYUROBROMIOE OEXTROMETHORPHAN HYOROCHLORIOE OEXTROMETHORPHAN HYDRO IODIDE TESTDSTERONEt 19-NOR/NANDROLONE/ N-NONYLCINNAMAHIOE CARAHIPHEN 2-METHOXY-4-ALLYLPHENOXYACETAHIOE~N~N-OlPRCPYL 2-METHOXY-4-ALLYLPHENOXYETHOXYACETAHIOE~N~N-OIETHYL 8-l2-HEO-4-ALLYLPHENOXY~-ETHANOLOXYACETAMIOE~N~N-OiET 1- lM-HE8ENZYL 1-3-IN-01 ETCAR8AMOYLl PIPER101 OiE
A A
8
27 46 46 46 26
2.33
3.07 1.42 1.26 0.15 0.51 0.33 0.30 -0.35 -0.45 3.74 2.97 3.06 5.08 5.36 -0.42 -0.70 5.43 0.00 1.98 2.16 4.43 1.06 0.75 0.59 3.28 5.45 0.99 1.38 0.98 1.51 2.02 2.02 1.21 3.96 0.64 3.61 1.97 1.81 0.41 0.20 0.05 0.03
17 17 17 17
8
8
l-lP-HE8ENZYL~-3-IN-OIETCAR8AMOYLIPIPERIOINE
1- I M - M EOBENZYL I- 1N-0 I E TCARBAMOYL IP I PER10 I NE 31-lP-MEOBENZYLI-3-IN-OIETCARBAMOYL~PIPERIDINE POTASS lUM DODECYL BENZENESULFONATE SODIUM OOOECYL BENZENESULFONATE P-T-OCTYLPHENOXYMONOETHOXYETHANOL/OPE-1/ N-HE-3-ETHOXYCAR8ONYLPYRlOINIUM NONYLSULFATE N - M E - 3 - M E T H O X Y C A R B O N Y L P Y R I O I N I U M OECYLSULFATE L I N O L E I C ACID OLEIC ACID P I P f R I D I N E v 1-OECYL I 3-1 N-ETHYLCARBAMYL) PIPERIOINEI 1-OtCYLt 3-1 NtN-OIMETHYLCAKBAMYL I OCTADECANOIC ACIO/STEARIC A C I O l TRIPHENYLSULFONIUM THIOCYANTE
353
57 464 464 479 479 478 478 479 96 499 499 143 130 130 130 56 143 4 56 456 456 482 482 4 46 46 31 31 31
0.26
8
8
0.06
N-PHENYL-P-PHENYLBENZAMIOINE N-PHENYL-P-PHENYLBENZAMIOINE
2 - H Y O R O X Y N A P H T H O Q U I N O N E t 3-(W-PHENYLPROPYLI DICLOXACILLIN CL OX A C I L L I N O X AC I L L I N OXYPHENBUTAZONE 2-nY DROXYYAPol hOQU IVOO'YEI 3- I n-CYCLOhE XE h-3YL-PRCPYL 1
62
4.00 0.98 0.55 0.32
3.28
4.90
=
A
62
7-CL-4~6-0IYEO-6'-ME-2'-PROPOXYGR1S-2'-Eh-3~4'-D10hE
7-CL-4~6-0IYEO-6'-ME-4'-PROPOXYGR1S-3'-E~-3~2'D~0hE
7-CL-6~2'-01ETO-4-YEO-6'-~EGRIS-2'-Eh-3t4'-01ChE
2.02 2.49 2.34 1.91 3.96 1.21 1.64 3.92 1.16 2.74 1.40 2.10 5.31 3.56 2.93 3.72 3.88 0.07 1.21 1.37 4.62 2.54 2.60 1.22 N N
RHOOIAU~~~~/~RIFLJ~TRIMEPRAZINE/ RrfOOIA~7746/TR1FL~OTRIHEPRAZI~E/
68
69 17 44 68 69 68 69 14 14 68 69 14 14 62 62 62 62 44 17 17 14 44
3
CHCL3 OCTPNOL CHCL3 CHCL3 N-I-EPTANE N-HEPTANE CHCL3 CHCL3 CHCL3 CHCL3 DIETHYL ETI-ER DIETHYL ETtER DIETHYL ETHER 0 1 ETHYL ETFER OCTANOL DIETHYL ETFER DIETHYL ETFER CHCL3 50XETHER+500DMF OCTANOL DIETHYL ETFER CHCL3 HEXANE CHCL3 OIETHYL ETHER CHCL3 HEXANE OIETHYL E T H E R CHCL3 HEXANE cHcL3CHCL3 01 ETHYL ETFER DIETHYL ETHER CHCL3 CHCL3 CYCLOHEXANE CHCL3 BENZENE ETHYL ACETATE N-HEPTANE N- P EPT AN E OIETHYL ETFER DIETHYL ETHER CHCL3 CYCLOHEXANE OCTANOL N-HEPTANE 483 482 482 276 4 82 482 485 416 482 482 500 500 143 465 465 465 483 501 501 500 125 483 466 466 4 66 466 466 466 4 66 4 66 466 466 482 482 378 457 482 482 474 474 474 474 498 498 143 465 486 446 235 421
8
I
1.11
3.92 0.59 2.29
N N
=
N N N N
0.88
1.95 0.85 1-60 1.57 0.45 5.93 3.92 3.20 4.10 3.88
A A A A
=
B 8
-0.88
0.41 -2.40
0.23
4.62 2.75 3.30 2. e2 1.69
=
A B
e
A 8
A 8
1.33
2.17 0.13 -1.12 1.54 -0.95 1.02 1.93 0.99
1.30
1.63 -0.86 1.10 1.57 2.41 1.80 2.82 1-81 2.15
68 69 44 62 68 69 14 14 14 14 62 62 46 44
N N
3.08
1.29 1.66 0.63 1.42 -1.52 1-66 0.34 0.89 6-70
A N N
0
10 .0
1.77 5.98 3.09 1.54
3.38
1.04 3.50
A A N
3. e3
3.64
3.83
C19HZlN103 C19H2 1N l S l C19HZlN3Sl C19H2 1N3S 1 C19H22N2 C19H22N201Sl C19H22NZOlS1 C19H22N201S1 C 1 9 H22N206 C19H2ZNZS1 C19H22N2Sl C19HZZN403Sl C19H22N403S2 C19H2203 C 19H2 2 0 4 C19H2205 C19 ti2 2 0 5 C19H23CL 1N2 C19H23N302 C19H2 3N302 C19H23N406PlSl C19H24CL l N l 01 C19H24N2 C19H24N2 C19H24N2 C19H24N2 C19H24N201 C19H24N201 C19 HZ 4N2 0 1 C19H24N201 C19H24N201 C 19H24N2 0 1 C19H24N201 C19H24N201Sl C19H24N201Sl C19H24N202 C19H24N202 C19H24N252 C19H24NZSZ C19 H24N402S 2 Cl9H24N402S2 C19H24N402S2 C19HZ4N402SZ C19H2402 C19H2402 C1 9 H 2 4 0 3 C19H2404 C 19HZ 5C L 1 01S 1 N2 C19H25N101 C19H25N101 C 19H25 N 101
TrfE8AIhE THEBAINE (PARAMORPHINEI 00 SUL E P I NE C Y AMEPROMAZ I NE CYAMEPRCMAZINE TRIPROLIOINE /PKA = 9.50/ A EPROMA2 I NE C AC EPRDMAZ I N E ACEPROMAZ INE BIS(P-AMINOSALICYLIC ACIO) AMYL ESTER M PAL1NE E MEPAZINE TH IAMINEIS-BENZOYL THIAMlNE*O-BENZOYL 2-HY OROXYNAPHTHOQUINON ET 3- I W-CYCLOHE XYLPROPYL) 2-HYOROXYNAPHTHOQUINONEt3-12-METHYLOCTYL-7-ONE) 2 - H Y 0 R O X Y N A P H T m ) P U I N O N E ~ 3-1 8-CARBOXYOCTYL) 2-HYOROXYNAPHTHOPU INONEt 3- 12-ME-bCARBOMETHOXYHEX) CHLORIM I PRAM I N ERGOMETRINE/ERGONIVINE/ ERGOMETRIN INE THIAMINE MONOPHOSPHATEIS-BENZOYL ZIA-ME-A-P-CLPHENYLBENZYL~OXYI-NIN-DIMEPROPYLAMINE IMIPRAMINE IMIPRAMINE IMIPRAMINE IMIPRAM INE 10-HYOROXYIMIPRAMINE 2-HY OROXY I M I PRAM I N 2-HY OROXY I M I PRAM I N E 2-HYDROXY I M IPRAMINE IMIPRAMINE-N-OXIDE I M IPRAMINE-N-OXIDE IM IPRAM INE-N-OX1 D E METHOTRIMEPRAZINE METHOT R I M EP R A2 I N E NvN-OIPHENVLCARBAMIC ACID~OIETAMINOETHYL ESTER lr4-NAPHTHOPUINONE~Z-W~CYCLOHEXYLPROPYLHYORAZINO METHIOMEPRAZINE METHIOMEPRAZINE THIAMINE BENZYL OISULFIOE THIAMINE BENZYL DISULFIOE THIAMINE BENZYL OISULFIOE THIAMINE BENZYL OISULFIOE l r 4-ANOROSTAOIENE-3r 17-OIONE 4 16-ANOROSTAOIENE-3~17-DIONE 2-HYOROXYNAPHTHOPUINONE13-NONYL 2-HY OROXYNAPHTHOPUINONE, 3-( 7-OH-7-ME THVLOC TYL I METHOTRIMEPRAZINE HY0RRS;HLORIOE NtN-OICYCLOPENTYLCIHNAHAMIOE PROPOXY PHENE CARBINOL PROPOXYPHENE CARBINOL

SIILVEVT
f-OilT NOTF

LOGP LlLT FIPIR ICbL FOAMULA
N N 4
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SEC
LWP SilLV
-1.15 1.95 3.53 c. 3 7 -ZSs)Z 3.24 2.73 2.86 3.2'3
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NAYE AMINOPROYAZINE AMINDPRCYAZIYE 11 4-YAPHTHllQUIUONF~2-YUNYLHYDRAZINO 4-ANDROSTEYE- 3t17-3 [ONE I9 ATR~lPINE-ETIiYL0R~lM E C I NCHON I N A Y I D E T N- ( 2 - 0 1 ETHYL-AY I NOE THYL 1 -2-PROPOXV N-METHYL-6-SROMOOU INOL I N IUM NONYLSULFPTE N - Y E T H Y L - 6 - C H L O R O O U I N O L I N I U Y YONYLSULFATE N - Y E T H Y L - 2 - I O ~ O Q U I Y 7 L I N I U M NONYLSULFATE EPITESTOSTERONE TESTOSTEROYE T FST O S 7 R O N E TESTIIST kRflYE TESTOSTEROUE C Y CR I M I N E PROCY CL I O I N E T E5TOST ERflYE OX1 ME N - Y E T H Y L - I - Q U I ~ O L I N I U M NONYLSULFATE N-METHYLQU I NOL I N IUM NONYLSULFA TE N-ME-8-OH-QUIYOLINIUY NONYLSULFATE 1-METHYL-3-AMINOQUIYOLlNlUM NONYLSULFATF 3-ETO-4-BUTOXYBENZOIC ACID+DIETHVLAMINflETHYL ESTER 3~4~5-TRIETtIOXYHENZ31C ACIO~OIFTHYLAMINOETHYLESTER N - M E - 3 - E T H ~ X Y C A R B ~ U Y L P Y R l O l N l U M OECYLSULFATE N-MC-3-YFTHOXYCARHflUYLPYRlOlNlUM UNOECYLSULFATE
5 3 0 1 CPCL? 5392 CtICL 3 7IETHYL ETCER 53-3 5 3 ~ 4 '< CF PT 4 h F 5 3 c 5 CHCL? 1LEYL ALCilHOL 5306 5 1 C 7 'HCl 1 5 3 r f l CHCL 3 53c7 c ~ r ~ 3 5 3 11 N - C F P T L Y F 5 3 1 1 lCTPNrJL 5312 I C T D N O L 3IETHYL FTIFR 5113 5l14 Y-CEPTAYE c 3 1 5 Y-VFPTANF 5 ? 1 6 Y-tEPTANE 5 7 1 7 Y-CEPTANC 531R CHCL 1 53 1 4 c HCL 537') CFCL3 5 3 7 1 CHCL 3 5372 OLFYL ALCOHOL 11 FYL ALCOCOL 5323 53 7 4 CHCL 3 5 3 7 5 CHCl 3 5 3 2 6 7CTAN17L 5 3 7 7 IlCTPNnL 532R Y-PKPTAYE 5 3 7 9 Y - C f PTPN E 53 79 CHCL 3 5 3 ? 1 CHCL 3 5 3 2 2 CCL4 5313 C C L ~ 5334 1C TPNnL 5 1 3 5 9)IETHYL ET+E9 5 3 3 6 CYCLOHFXAYF 5327 ICTANOL 53'8 I-PLTANCIL 5 3 3 9 OrTANflL 'JCTINOL 534" 5 3 4 1 CHCL 3 HEXANE 534) 5 1 4 3 HEXANE 5 3 4 4 7CTPNDL 5 3 4 5 CYCL PHFXAYE 5346 IILS 5 3 4 7 CHCL? 5 7 4 8 CHCL 3 5 3 4 9 CHTL3 5350 ilr T CN1L 5 7 < 1 lCTPYOL 5-35? IIETHYL E T C C R 5 3 5 3 STNIEYE CTCEP 5354 31-I-PR. 5 1 5 5 Y-CFPTANF 5350 CHCL 3 5 7 5 7 c Y t L nt i F x AN E 5 3 5 8 CYCLPHEXANE 5 3 5 9 CllTTHYL ETkER 7IFTHYL ETkER 536" 5 3 t l OIFTHYL ETCFR 5 3 6 2 CHCL 3 5 3 c 7 111 5 5 3 6 4 CtJCLS 5365 7 I F T P Y L ETkFU 5 3 6 h > I FTHYL FTFFR 5 3 6 7 3IETHYL ET+FR 5 3 6 8 N-+EPTANE 5369 5770 5371 5372 5373 5374 I I L S )I FYL ALCntCL 5375 5376 OCTANCIL 5 ? 7 7 nCTPNOL 5 3 7 8 CHCL3 5379 CHCL7 5 3 8 1 CHCL? 5 3 P l Y-P'FPTANE 5 3 8 7 U-+rPTAhE 5 3 8 3 1LEYL ALC3HflL 5 3 8 4 CHCL3 5385 CHCL3 5 3 8 6 CHCL7 5 7 8 7 CHCL 3 538R C P C L l 5989 CHCL 3 5390 1 C T CNqL 5 3 9 1 CllCL3 5397 CHCL 3 5393 CHCLS
4H2
462
457 4 )E
491 489 464
68 69 62 46
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7.43 3.57 3.77
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464 464
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3.32 1.31
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477 498
0.32 2.51 1.75

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464 464
2.71
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523 473 473 464 464 65

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443 443 412 412

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504 277 4H2 456

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3.67 -1.15 1.16
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2.17 1.27 1.72 4.92 4.22 3.40 -C.73
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3.67 -7.12 1.16 -1.R5 2.63 4.92 -0.~5 7.2R 1.95 1.73 1.83 1.h5 1.39 2.17
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483 141 5115 4R2 486 482 186 218 3 405

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N N N
23 h8 6R 17
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1.44 1.73 1.93

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1.23
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416 432 495 495 143

143
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405 486 505 482 143 143

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4.27
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3.87 C.23
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4.40 4.19
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23 68 62 67 62
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491
142 142 218 216 462

489
2.61 -1.22 7.29 7.13 2.67 -3.49 -1.32 1.45 1.80 4.41
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216 216 464 464 464 4'3R 477 142

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2.64
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C19H25 N3S1 ClYH25N3Sl C19H26N7C2 C 19 H2 6132 C19H27HKIN103 C19 H2 7N302 C 19 ti28 3 9 1N 1345 1 C19H2 8C L 1 N104 S 1 r19H2111U10451 r19HZH02 C19H2812 C 19 H2 RO2 C19H2902 C 1 1 H Z RO2 c 1 9I i 2 9 Y 1C l C19 H29N 1C1 ClYH29NlCZ C 19 H7 )N1@4S1 C 19 H29Y 1 0 4 5 1 C19H2Y N l C 5 S 1 C19H30N204Sl C l Y H3 1h 1 @ 4 C19H3 1N l C 5 C 19H3 3N 1 0 6 5 1 C 19H3 3Yll-6 5 1 C19H343RlNl ClYH34RKlNl c 2 c iii 3 N 1s I C2CH13NlSl C20HlbCUlN232 CZCH16CUlN2O2 CZCHlbCUlN202 C2C H l 6 C U I N 2 0 2 C20 H l b N Z C 4 C20 H16 04 CZCH19NlO2Sl C20H19N103 C2OH19N105 C2@H19N108 C2C H2 2 N8 1'5 C?CH23CLlN2Sl C2nHZ 3 CL 1 0 6 C20H23CLlflb C2OH23N 1 CLOH23Y104 CZOH24CLlN301 C20 h24C L 1N3S 1 C2DH24CL2N2Sl CZtH24N2nlSl c2rti24~20~ C2OHZ4N2C2 C2CH24NZO2 C2PH24N2C2 CLPH24YZ07 CZ"H24N2Ch C23H24N2Sl CZCH24N402 LZP H24 N402 c 2 c ti2 4 03 C L r H2401 C2C H74U4 C 2nH25C L2N3S 1 C 2 IHZ 5 N3 C Z C HZ 5 N 3 S 1 C2CH2603 1 C2 f H? 6 1 7 C2'?H2605 C2OH28N2C3 CZCH29RRlN103 C2C H29NlIJ2 C20H29N102 C2nH29N302 C2PH29N3C2 C 2 1 H29N3C2 C2CH29N302 C2DH29N302 .C2H402 CZnH29N302. C8 H604 C 2 C H3CHR 1N 1 0 4 s 1 C2C H3" CL 1N104S 1 C ~ P H i ~~ ~ 0I 4 s i i r7c H3 '02 CZnH31YlCl C Z " H3 1Y 1r7 c2r H3 1N11145 1 C2C 1 3 1N 1@4S 1 1 r 2 c n 3 ~ ~ 1I~ 4 s C2C H3 1'41 0 4 5 1 u r1 1 3 i ~ i r 4 s 1 r~rt13i~tr4si C2[ I i 3 1 ~ 1 c 4 s l CP'H~lY1C5S1 C 7 1 1 1 3 1 N 11'55 1 C?'H31Vlr551 c2r t i 3 ~ u z ~ 4 s i C 2 t l x 2 N6 C 12 S 2
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PH NOT H I A 2 I Y E t 1 t 2789 9 - 0 IBENZO R-PUINOLINOLOI 2-METIiYL I { B I S I - C U ( 11 I 8-OUINnLINOLO(4-METHYL I ( E I S l - C U l I 1 I 8-QUINCL IUOLO, 4-METHYL(BISl-CUI 1 I I 8-QUIYOL INOLOI 2-METHYL ( E I S I - C U I I 1 I CAMPTOTHECIN (NCS 9 4 6 0 0 ) 2-HYDROXYNAPHTtiOPUIUONE~3-~3-P-TOLYLPROPVL-3-ONEl 1~4-N4PHTHOQUINONE~2-ANlLINO~3-BUTYLTHIO ACRONYCINE (NCS 4 0 3 1 6 9 I l P K A I N 40% MEOH- 3.401 BERBER I N E 4-OEOIMETHYLAM INOTETRPCYCLINE METHOTREXATF IPKA I N 30% YEOH = 4.701 SANOOZ#6524 2'-BUTOXY-7-CL-4~6-Ol~E~-6'-MEGRlS-2'-EN-1~4'-0IONE 4 ' -BUT O X Y - 7 - C L - 4 , 6 - 3 1 M E O - 6 ' - M E G R I S-3'-EN-3 92 '0 I ONE AMITRIPTYLINE A-CARRETH3XY-8-ANILINO-B-PHENYLPROPIONIC ACID,ET.EST. P C R I DINE. 2-CL-7-MEO-512-01 ETAMINO-2-E T A M 1 NO1 PROCHLORPERAZ I N E 2 - C L - l O - I 2 ( 2-Y-MFP IPER IDYL IETHYLIPHENOTHIPZI NE HCL PROP 10 VAL I NE OUININE (311 I N I Y E OU I N INE QUININE UUINIYE R I S I P - P Y I Y I S A L I C Y L I C P C I D l HEXYL ESTER SAUOflZ#5457 H E N 2 I Y I CPZOLFI 1-01 ETHYLAY INOETHYL. 5-NI TRO.2-RENZYL BENZIY I OPZOL E. 1 - 0 IETHYLAMINOETHYLt 6-NI TRO.2-BFNZYL 2 - ~ Y O ~ O X Y N A P H T t J f l Q U I Y 0 N E ~ W-CPREOMETliOXYOCTYL) 3-( 2 - r Y D R O X Y N A P t i T H O Q U I Y D N E I 3-1 W-CYCLOHEXYLBUTYL I
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2-METHOYY-4-ALLYLPHENOXYACETAMlUE~N-DI-l-RUTVL
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SOLVENT CHCL3 RFN I EN F 9EN 2 FU F RENZEhiE BFNZENE CHCL3 D I FTHYL ETFER PARAFFINS PARAFFINS PARAFFINS IICTANOL 7CTbNOL I-PUTANOL OCTPNDL DIETHYL F T F E R CHCL 7 DI-I-PR. ETI-FR OCTANflL CHCL3 CHCL? 'ICTAN3L ETPYL OLEATE CHCL3 CHCL3 CHCL3 DO O E C AN E OCTPNOL 3CTbNOL CHCL3 N-HEPTANE OILS CHCL3 CHCL 3 CHCL 3 CHCL3 Y-P'EPTANE ChCL3 3IETHYL ETFER I-BUTANOL OCTANOL CHCL 3 D 1 ETHYL ETFER DIETHYL ETPCR ETPVL OLEATE CY CLOHFXANF CHCL 3 CHCL 3
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NAME
N - M F - ~ - Y ~ T H ~ X Y C A h H 3 ' 4 Y L P Y R l ~ l N l UOOECYLSULFATL UM P I PER I 0 I N F 1 1-1)EC YL t 3- I N- PY K O L 1 0 I NO-F O R M Y L I ~ PIPE?.lCINEI 2 1-DECYL? ~-IY-YO9PH?LlND-FORYYL)
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Y-HFPTANE Y-bEPTANE PRIM. PENTAYflLS HEXANOL n I F T H Y L ETbEQ DIFTHYL E T b F R HFXANF DIETPYL ETkFP n l E T P Y L ETFER 'ICTPNQL CJCTAYQL D l FTHYL E T k E R SENZEYE I-BUTANOL > I T H Y L ETkFR OIFTPYL E T k E R hi-PEPTANE OCTPNOL 3IETHYL ETkER I -BUTANOL D l ETHYL ETIER OCTANOL N-PEPTANE HEXANE Y-tFPTANE "II-EPTAYE Y-I-EPTINE OCTPNOL 3 l E T H Y L ETHFR RENZEYE DIETHYL ETFER DIETHYL E T F E R BENZENE I-eCTANflL CHCL 3 CYCLOHEXANE OCTANOL OCTANOL OLFYL ALCOI-OL CHCL3 CUCL3 CHCL7 CYCLOHEXANE CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 ICTANOL CHCL3 CHCL3
499 776 5 0 4 40 1 3 0 I? 2 18 3 17 556 4 ~ e 504 40 482 68 4 8 7 69 218 494 482 68 h9 482 402 68 475 469 475 46 4R6 4 6 477 505 27 68 482 482 68 482 6 8 482 69 416 14 482 68 143 62 130 227 486 46 502 502 494 495 68 452 482 69 322 1 3 6 44 136 44 1 8 1 1" I 8 1 18 1 4 3 b2 143 62 5c7 502 50H 227 7 19 5nz 5c 7 130 12 502 5C8 477
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502 130 502 261 498 507 498 49R 498 261 502 507 5Ci2 508 507
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PKOPOXYPHENt RHODOYYC I N THIFTHYLPESAZINF THItTHYLPERAZINE PU R C Y Y C I Y

2 - H Y O R O X Y Y A P H T H O Q U I U O N E I 3-DOOECYL 6-A-YETHYL-DREPNISOLONE Y F THY L PR E 9 Y I SOLfl \I E 9 A FL 11 B -0I i 6 A 4 F 4- P P EGUF N F 3 2 C- 0 I ON E 6 - d - Y E T H Y L - 9 - A - F L U ~ 9 O - D E S O X Y H Y O R U t O R T I SONE A T R r J P I Y F - U - AYYLSROY I D C I NCHIN I N A Y I DEt N-I 7 - D I ETHYL-AM INOE THYLI-2-HEXOYY N-f~ETHYL-6-RR-QIlINJL I N IUM OODEYLSULFATE Y-YETHYL-6-CL-PUINIL I N I U M OOOEYLSULF ATE N - M E - 2 - I O 7 ~ O U I N O L I V I U Y OIIDECYLSULFPTE 1 9 2-OIYETHYLQUINOLIYIUY UNOFCYLSULFATE 1 . 4 - 0 1 HETHYLQU INOL I V I U Y UNOF CYLSULFATE 1t 6-01 METUYLQIJ INOL I V I UY UNOECVL SULFATE 1, 8 - D I YETHYLQU INnL IUI UY UNDECYLSULFATE N-MFTHYL-I-OUINOLINIUY DOOECYLSULFATE N-YETIiYLOUINOLINIUU DODECYLSULFATE 1 ~ 2 r 6 - T S I M E T H Y L O U I N O L I N I U M OECYLSULFATE 1 1 2 1 6 - T R I Y E T H Y L O U I N J L I N I U M OECYLSULFATE N-ME-6-YETHOXYOUINOLINIUM UNDECYLSULFATE N-ME-8-METHOXYOUINOLINIUM UNDECYLSULFATE N-ME-8-OH-OUNIN~LIYIUM OOOECYLSULFATE 1-METHYL-3-4MINOOUIYOLINlUM OOOECYLSULFATE P- T - I C T Y P n E % J X V T P I E T h3 X Y E T n A h '3 L /O PE 3 I . (,- 3 8 J' I X V t AL 0'3\ Y - 0 Y R I 7 I h I M O @ EC f L 5 UL F A T E UF h I - M E - 3 - ~ E T ~ ~ X V C A R R l ' f Y L P Y ~ l O I \ T i~l 9 4 O E C V L S J L F l J~ I r Z15-TRI'4ETHYLPYRIDIN IUM TETRADECVLSULFATE PIPE4IOINE~1-OECVL~3-lN~N~-DlPROPYLCPRBbMYLl 11 ~-NAPHTHOQUINONEI2 - A Y I L I N 0 93-P-TOLUIDI NO SULFINPYRIZONE 2 - H Y O R f l X Y N A P H T H O O I J I V O N E ~ 3-W-Q-TETRALYLPROPVL MALACHITE G'IEFN BRUCINE BRIJC I N E
- - - -
-- - -
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62 17 36
3 753 4 502 5C 2 5c4 514 5?2 143 4H6 5 '2 4H2

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2.33 5.77 r.62 -r.74 0.11 1.42 2.39 1.93 -C.Q4

c.J5
n.62
Q.19
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-C.36 1.35
3.h3
4c 62 46 68 69 46 23
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1.66 7.37 9.67 1.57 -1.4n 1.71

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3.19 -c.34 c.q5 2.92 6.59 1.2c 2.9h -r.7c 2.2c 3.17 2.74
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7.41
1.91
482 136 I36 136
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2.29 1.35 2.'12 r. 9 5
C23H2ONZC381 C ? 4 IH2 2 0 3 C23 H25 CL 1N2 CL3H26N2C4 C23H26 Y204 C2 3 H26 N204 C231127CL 1 F 2 0 6 C23 H27F3fl6 C231127N307 C23H27N307 C2 3 H2 8F2C6 C23U2803 C23H29CL2Y302SI C23H29 F I C 6 C23H29N30251 C231i29Y3C281 C2 3 1139 D 9 I N1O3 C23H3JCLIN301 C23 U3 ) F 2 05 C23H3JNZClSl C23ti3'N204 C73 H31N2C4 C23 H3 > N 2 C 4
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BRUCINE b~9-A-OIFLUORO-16-A-TL-PRFDNISOLONISOLONE
6.91
16-A-TKIFLUORO-PREONISOLONE
ACETATE ACETATE
9-UIYEAMIY I - 6 - D E M E T H Y L - 6 - D E O X Y T E T R A C Y C L I N E MINOCYCLIYF 6-A-16-A-DIFLUORO-PREONISOLONE ACETATE 2 - 9 t ) R J X Y \ A ? h T d C C J [ \ ? \ E , 3 - 1 - TH-9-DECAL VLPROPYL T n l 3 P 9 T P A 2 4 l E bVCR'3C-LJ9IOE 6 - A-GL J J C - ~ R E ? 4 1 S I i ~ t\ ACETATE ACETOPHEY4LINE A C ETOPPEYAZ INE PROPANTHEL I U E BROMl9E ACRID1 NE, 2-CL-7-MEO-512-01 ETAMI NO-5-AM-AMI NO1 6- A 9- A 0 I F L UO RO 2 1 0 E SO X Y- HY OR OC OR T I SONE AC E T AT E S A NIJO 2 Y K S 7 '> M I TR 4C I L I A T l h E I P SU EO0 CONF I G M I T R AGYN I Y k I A L L O C3NF 1 6 . / S P E C I O C I L I A T I N E I F P I A L L O CONFIG./
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NOTF

FMPIKICAL Fc! Q M L A U C23H31Y2C4 C23 HlOY2C6 C23130U7C7 C73 ti3 7 O h C23 H 3 G l 6 C73ti30M C73H3 l F l l i 6 C77H31F 106 C 2 3 H3 1N 10 2 C23 H3 1N 1C? C23H31NlC4Sl C23H31N3n1 C 23 ti3 7 0 6 C73 H32Oh CL3 H 3 2 0 6 C73t132ilh c 3 113 3 I 1u 2 r~ 1 C23H34NHT3 C23H3404 C23 H356R 1U 1 0 3 C7 3H36NR C23H35YH C23H36N301 C23H36V9Cl C 7 3 ti1h YH l J 2 C23H36YRO3 C23HJ6N503 C23H36N803 C23H3bYlCO2 c 2 3 113 7 c L 1N8 C23H37Nlr451 C23 H3 7Y 1C4S 1 C23 H3 7Y 1C4S 1 C27 H 3 7 Y l C 4 5 1 C23H3 7 N l C 4 5 1 c 2 3 H3 7 ~ 1 0 41 s C23H37N10551 C23 H 3 7 Y l C 5 S 1 C23H3YNY C23H3dNHOl C23H38N801 C23H3dN801 C?)H38(YRO2 c23 ~ 1 3 8 ~ ~ 0 2 C73H3dU802 C2 3 H38N9@2 C23 H3 3N8C2 C?3H31NRO3 C23H4N8 c 7 3 ti43 Y R C73H4INYCI c 7 3 ~4 1Y in 6 s 1 C23H41Y 1C6 5 1 C7 3 it42 S R 1Y 1 CL3 H4oH6C13 C74H2jAS1D K 1 C24H2 - 4 5 1CL 1 C24H2ASlU132 C74ei23 P S I N 1133 C24H23811Pl C24H2dQ134P1 C24H21CLlP1 C24H2 1 11P1 C24H21NlPZP1 c 7 4 142 n v i 0 3 P 1 C24H21ASlU3Sl C24H2lAS103SZ C24H2 2 4 5 1C R 1114 C24H22 ASlCR104 C24H22AS l O 4 P l C24H22CR 1 O 4 P l C?4 H2 2CR 1O4P1 C24H2234PZ C24H2 5Y3 C24H28N408 C24H2 R N4C8 t 1 4 H30F2C6 C24ii?@ 206 F C 2 4 H3 3 F 2 P6 C24H3 I F 105 C24 ti3 1F 1C6 C24H3 1F 1 0 6 C ?4H3 1F 1C6 C24H31F 1 0 6 c 2 4 ~1 ~ 3 c l s l 3 1 c 2 4 ti3 1 ~ 3 0s1 C24 1-13 1N 31125 1 C24 H3 I N302 S 1 C24H32CLlN301 C24H32N7Cb C24t132 I6 C24H3204 C24H3 3 F I C 6 YAME SPtCI7GYVI\I/NlRMAL GUYFIG./ H I S I P - A Y I Y I S A L I C Y L I C A C I D 1 hIONYL ESTER XANTH13MYC I\! CURTISOYF ACETATF P9 E l l ? I S l L J N F A C F T A T F P I F O Y I SCILJYE ACCTATF 9- A - FL U f l K l 3 - I ~ Y 1)RP C l i 3 T I S O N t A C F T A TE 9- A - FLU I19 O H Y DRrJ C L1R T I S O lu E ACE T A T E A.A-OIPHEVYLVALEQIC A C l O r I)IFTHYLAMIN[lTYYL ESTER SKF 5 2 5 1 /PKA = 8 . 3 7 1 Y-YETHYLACRIDIYIUb YINVLSULFATE R E Y Z I Y ICAZOLE, 11 2 - D I F T - A N I N O ~ 2 - M F lFTq2-P-ETO-RFNZYL H Y 3 4 f l C O & T I S O N E ACETPTE HYOROCCRTLSONF ACETATE HYDRijCORTIS2NE ACETATE G - S T R 7 P ti 4NT H I I I N 1 ISLIPR3PAYI D E PK E:)% I SJY ED I GLJ AN YL Y Y D K AZON E DIGlTOXIGEYIY ATP~PINE-Y-HEXYLRFOYIDE D- I-PROSES T E R D N E O I N A Y YL HYDR AZONE O-6- PKCGEST FQIJNFDI GIJPN YL HYOR AZ?NE
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SPLVFNT Y-HEPTANE Y-HEPTANF CHCL3 DIFTHYL ETFER DIFTIYL ETCER DIFTHYL ETCER 01 ETHYL FTCFF. D I FTHYL ETCER OCTANOL 1 C T ANqL 1 CHCL 3 CYCLflHFXAN E DIETHYL FTI-ER J I ETPYL ETFFR 71FTHYL ETCER I -PUTANOL CHCL1 N-BUTANOL I-BLTANOL CHCL3 N-LIUTANOL Y-SUTANOL N-BUT4NOL N-BUT4NilL Y-AUTPNOL N-BUTANOL Y-BUTANOL Y-RUTANOL N-BUTANOL Y-PUTANilL CHCL? CHCL 3 CHCL3 CHCL3 DCTANOL CHCL3 CHCL7 CHCL3 N-BUTANOL Y RUT ANOL N @LIT OL AN N-BUTANOL N-BUTANOL N-EUTANOL N BUT AN (1 L V-PUTANOL Y -EIJTANOL N-RLTANOL Y-BUTANOL N-RUTANOL Y-OLTANDL CHCL3 CHCL 3 rlCTANOL Y-PLTbNilL CHCL 3 CHCL 3 CHCLX CHCl7 CtiCL 3 CHCL3 CHCL 3 CblCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 CHCL3 PARAFFINS CHCL3 CCL4 DIETHYL ETCFR 3IETHYL ETCER DIETHYL Eli-ER DIETHYL ETbER DIETHYL ETCFq DIETHYL ETCER D 1 ETHYL ETI-ER D 1 FTHYL ETCER CHCL 3 CHCL3 CHCL3 CHCL3 3ILS Y-PEPTANE DIETHYL ETFER DIETHYL ETI-FR D I I T H Y L ETI-ER CYCLOHEXANE CHCL3 ETHYL ACETATE CHCL3 N-BUTANOL N-BUTANOL N-PUTANOL
LOGP SOLV 1.44 2.32 1.05 1.40 1.33 1.11 1.66 1.23 3.47 4-65 4.65 1.4H 1.42 1. ,29 1.11 c.95 -c.70 n. 7 0 1.95 -c.74 1.54 1.47 C.82 1.92 1.5H C.38 C.51 c.59 c.99 1.65 4.35 4.58 4.73 4.42 5.45 4.66 4.52 4.77 1.52
0.88 0.03
LLGP OCT
5601 5602 5603 5604 56r15 56C6 56C7 56C8 5609 5610 5611 5612 5613 5614 5615 5616 5 6 17 5618 5610 562q 5621 5622 5623 5624 5625 5626 5627 5628 5629 5630 5631 5632 5633 5 6 34 5635 5636 5637 5638 5639 5640 5641 5642 564 3 5644 5645 5646 5647 5648 5649 5650 5651 5652 5653 56 54 5655 5656 5657 5658 5659 5660 56C 1 5ht2 5tC 3 5664 5665 5666 5667 5668 5669 5 6 70 5671 5672 5673 5674 5675 5676 5677 5678 5679 5680 5681 5682 5683 5684 56E5 5686 56e7 5688 5689 5690 5691 5692 5693 5694 5695 5696 5697 5698 5699 5700
136 416 512 502 592

5CR
44 14 57
502 5ca 56 276 464 495 502 513 5CR 130 405 159 131 491 159 159 159 159 159 129 159 150 I59 159 464 464 503 464 503 464 464 464 159 159 159 159 159 159 I5Q 159 159 159 159 159 I59 464 464
65
2.68 2.61 1.85 2.92 1.95 3.47 4.65
5
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C.86
46 46
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1.71
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5.45
46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46 46
514 95
95
1.12 r. 34 C.51 c.54 c.59 c.75 0.31 1.11 1.56 C.76 4.27 4.60 2.72 O.61
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c.53 -0.C8
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95 95 97 97 97 97 97
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68 69 60 69 23 14
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SOLVENT R E F FOOT NOTF 503 464 57 95 268 502 283 505 502 5C2 464 532 502
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LOGP OCT 5.9r EMPIRICAL FORMULA NAME
NC.
LOGP SOCV 5.90 5.13 2.03 1.53 c.96 1.54 -1.37 2.13 2.40 1.73 5.45 2.39 2.35 c.22 2-42 5.12 3.28 r.34 2.95 3.18
5 7 0 1 ICTPNOL 57C2 CHCL3 5 7 c 3 ICTPNE 5 7 c 4 CHCL3 5 7 c 5 1CTAN3L 5 7 ~ 6 DIETHYL ETCER 5 7 c 7 I C T ANIL 5 7 r ~illLS 5 7 Q 9 JIETHYL E l F R 571" 3IETHYL FT E R 5 7 1 1 CHCL3 5 7 1 2 ?IETHYL ET E R 5713 )[ETHYL ET ER 5 7 1 4 CHCLS 5715 CHCL3 5 7 1 6 CHCL 3 5 7 1 7 ICTANPL 5 7 1 8 TOLUEYF 5719 TOLUENE 572P TPLLEYE 5 7 2 1 TCLUFYF 5 7 2 7 TnLUFYF 5 7 2 1 T fl L UEY E 5724 TOLUFNE 5725 TOLL'YE IF H L TY ET~ER 5726 5 7 2 7 CJIETHYL FTI-EQ 5728 C H ~ L ~ 5 7 7 9 OrTPhlF 5 7 2 n CHCL 7 HEN7 E Y E 57'1 5 7 ? 2 T 0L 0 EY F 5773 t C L 4 5 7 3 4 CL CVZCtJ2CL 57?5 JIFTHYL FTkER 5736 9ICTHYL ETCER ni FTWL E T ~ F P 5737 5739 'JIETHYL E T t E Q 5719 3 I E l H Y L ETtER 5740 CHCL3 5 7 4 1 DIETHYL ETkER 5742 DIFTHYL ETkFR 5743 Y I X F D s r i L v i l i 5744 7CTANF 5745 l l F T H Y L E T t F R 5 7 4 6 HEXANF 5747 CHCL3 5749 CHCL 3 5749 lCTANF 57 50 CHCL3 5 7 5 1 3CTPN1L 5 7 & 2 CYCLfl?lFXAYE CHCL3 E753 5754 CHfL3 5 7 5 5 2IFTt'YL F T t F F I-eUTANCJL 5756 5 7 5 7 ChCL3 57 58 ?CTANE 5757 > I E i r y t E T ~ F R lIFTHYL FTkEQ 576' 57C 1 'IIETPYL FT+EQ. 5 7 c 7 3IETHYL E r t W 57CS C H f L 3 5 7 6 4 OCTANE 1IETtiYL FThFP 57t5 5 7 h n ' I C T AN3L 5 7 6 7 ill ETHYL ETkER 5768 71ETHYL ETkER 5769 ICTPNIJL 5 7 7 0 I1CTPY7L 5 7 7 1 OCTANE 5 7 7 2 OCTCNOL 5 7 7 3 OIFTHYL FTkEP 5 7 7 4 CYCLCHEXAVE 5775 CHCLl 5 7 7 h HENZENE 5 7 7 7 TO L U EU E 577R ETrYL ACETATE I-PENT. ACETATE 5779 5787 CCL4 FTkER 57E1 '31-I-PR. 5 7 8 2 Y F - I -3U 5. K E TON F 5 7 8 3 'I CT n N l L 5784 D I E T I J Y L ETkER 5 7 f 5 CYCLnHEXANE 5 7 f 6 CHCL 3 5 7 8 7 JENZEVE 5786 TPLUEYF FTPVL ACETATE 5789 5 7 9 q CCL4 5 7 5 1 f > I - I - P R . ETtFP 5 7 5 2 '4 E I aU T K E T'iN E 5 7 5 3 7CTAN;)L 5794 'ICTAN'IL 5755 3CTANOL 57Sh TOLUEYE 5 7 5 7 OCTANOL 5 7 5 8 3C.TONOL I-PUTAYOL 5799 5800 3CTPYOL
46 46
59
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= = =
R
= = =
1~2~b-TRIYETHYLOUINiJLIYlUM OOOECYLSULFATE C24H39N10451 C24H39NIfl4S 1 1. ~ P ~ - T R I Y E T H Y L Q U I N O LI U Y OODECYLSULFATE IN C24H4206 P-T-OCTYLPHENOXYTETRAETHflXVETHANOL/OPE-4/ TETKAPHENYLARSONIUY THIOCYANATE C25HZ?ASlNlSl GENTIAY VI3LETlCPYSTAL VIOLET/ C25 H3 I C L 1N 3 C25H33F 106 6-4-METHYL-TRlAMCIN9LOYE ACETOYIOE C25 H3 3N 1C4. HCL ETORPHIYE HYDROCHLORIDE C25H34CLIN301 A C R I D 1 NE, 2-CL-7-MEO-51 2-01 E T A M 1 NO- 7-HEP-AMI NO1 c 2 5 ti3405 6- A-ME THYL 2 1-DES0 XY-PR EON I SOLONE PROP I ONA TE CZ5H35FlC6 6-A-YETHYL-9-4-FLUORO-16-A-HYOROXYCORTISONE ACETONIDE C25H35N10451 N-METHYLACQIOINIUH UNOFCYLSULFATE HYOROCflRTIS0NE-21-SUTYRATE C25H3hOh HYOROCURTISONE-21-I-BUTYRITE C25 H3606 AT R f l P I NE-Y-UCTYL B P 3 Y I DE C75H39RRINlJ3 HOMATRJPIYF-NOYYLSULFATF C25H4 1N107 5 1 C75 H45N 1C6 S 1 N-ME-3-8Ut JXYCARBONYLP YP IOlFtlUM TETRAOECYLSULF. RENZYLOIYET*YLHEXADCCYLAMM@NlUM BROMIDE C25H46HR 1N 1 CADMIUM-CARRAZDNE CaJYPLFX C26 H2 2COl Y8 02 CUPRIC-CARUbZdNE C'JYPLFX C26H22CUlNd02 FERROUS-CARBIZONE CIMPLFX C76 d 2 2 F E 1Y802 M A NG A OUS - C 4R R AZDY F CO YP LE X N C26H22 MY 1N802 PLUMBOUS-CdQEAZllNE COMPLEX C26H22NRfl2PRl STANNOUS-CARHAZONE COYPLEX C26H22N8@2SYl C 26 H2 2N8f72 Z N I ZINC-CAQEAZONF COMPLEX C26H22NI 1N802 N I CKEL-CARRAZONE COYPL EX 6- 4-FLLJORO-DEXAY ETqASONE-2 1-BUTYRATE C2 6 H34 F2 0 6 6-A-FLUORO-3E X A Y E T H 4 S O Y F - 2 1 - I - B U T Y R A T E C26 H34F2 P6 AT ROPI NE-Y-YONYLBROY I D C2b H14 1 i ) R l N 1q3 P-T-OCTYLPdENlXYPENTAETHnNOL/OPE-5/ C26Y4607 490WTHYYOLBLUF C27H28RR205Sl BROYTHVMOL HLUE C27H28RR205Sl EROYTHY YIIL 9L UE C27HZRBR20551 I 9 OMT HY YOL 4L LJ E 3 C27H2HHR205Sl BACYTHYYfJLBLUE C27H29BK20551 6-A-YE-9-A-FL-PREOUISOLUNE-16, 17-ACET~NIOE-21-ACETATE C27H3 5 F 1 0 7 RFTAMfTH4S~lYE-17-VALFRPTE CL7H37F l P 6 BETPYETHAS3YE-17-VPLERATE C27H37F1C6 6-A-'4E-9-4-FL-HYOROXYCOF T I SONE-ACETONIOE-2 1-ACETATE C77H3 7F 1C7 HVOROtORTISONF-21-C4PR9ATE C2 I H4 3 0 6 ATROPINE-N-DECYLRR94 I D E C 2 7 ti4 7 R Q 1Y 1 0 3 6-A-YETHYL-TRIAMC1'43LUNE ACETflYIOF-21-PROPIONATE C23H37F107 6-A-ME-9-A-FL-HYDROXYCORTISONE-ACETONlOE-PROPl~NATE C28H39F107 B A R Y I T J R IC ACI DI 1-Y-OCTAOECYL-5r 5-01 ALLYL C2Ll H48N203 P-T-~CTYLPtiENOXYHEXPETH0XYETHANPL/OPE-6/ c2a~5-m DEUTEXC-P0QPHVPIPd C3>H3"h404 GRISEOFULVIN. T E T K A - 4 C E T Y L - Z ' - G L U C O S Y L O X Y C 3C H3 3 C L 1 0 15 METHAYTHELIYE-NONYLSULFATE C3cH45NlC7S1 OXVPHFNONI JY-VOVYYL S JL FATE C3C ri53FllC7S 1 P T 0 C T Y L P H EN0 X Y HF P T A E T Hfl X Y E THA NOL / 0 PE 7 / C9CH54d39 TRIDIHEXYL-U3YYLSULFATE C3r h 5 5 N K l 5 5 1 r3! h32'3H2N6 11 hCS-113 ) Q 5 I VITAMIN K ) l14-UAPHTY'12U1YOhF9 Z-METHYL13-PHYTYL C 3 1ti4607 HE Zr Z r l M FT H4 4 I Y E -UnN Y L ZUL F A T E C31 Y53 N2 C5 S 1 PqOPhYTHEL IYE-NONYLS3LFhTF c 3 2 H49 Y 1 r 7 5 1 CEVADIYE c 32 t i 4 5 1\ 1c 9 CEV4OIVE r 3 7 ~4 1 Y 1 r-9 C ~ ~ Y ~ Z 1Y Z ~ ~ S IS O P R O P 4 M 1L)E-UONYL S'JL F4T E P-T-OCTYLPYFNlXYOCT~FTriOXVETH~N0L/nPE-8/ C 32 r(5 J J ' 1 PdnTIl-PnRPHYa I Y C34Y34Y4C.4 HCYAT l-POKPHYQIh C 3 4 tf38Y4C6 YESO-PORPHYRIU C 1 4 Y 3 8 Y4Ch ACCYIT l l r E C34H47UlCll PCCUIT I Y i I 1 C34 1 4 7 iu 1C 1 1 P-T-ICTYLPHENIXVNO~~ETHPYYETHANCL/OPE-9/ C34 116 2 I 1 1 : M O h U D F q E T H Y L -L-CUt? IU 5 3 5 H3 6N2flh 3-82 1 3 0 - 3 ' +E( OIMEAY I Y J 1 - 4 ' - I i Y n R C X Y F R Y T H R 3 * Y C I N C35 H6 1lu3C14 C- CHON DR3CUU I N E C3bH311Y206 COPRO-PORPHYRIN C36H38Y4PR N-DFSYETHYL EQYTHHOYYCIN C3h1165N1013 ERYTHROYYCIN C C36H63YlC13 P-T-3CTYLPHEkOXYDEC4ETH@XYFTdANOL/OPE-l'3/ C36 H 6 6 9 12 C 3 7 H6 7 N1012 C37 H67 Y 1 P i 2 C37H67 V l L 1 2 C37 L(67 N l C 1 7 C37d67 N1512 C37H67Y l C l 2 C37 -67 N1 0 12 C37 H67N 1P l 2 C17Hh7Y 1012 C37Hh7NlCI2 C3 7 H67 N1C12 C37H67NlUl 3 C37H67NlC13 C37H67N1013 C 3 7H6 7 N 10 1 3 C7 7 H67 Y l " 1 3 C 97 H67 N1013 C37Hb7 N l C 1 3 C37 H67 h 1 0 17 C 17H67N1013 C77 H67 N 1 0 13 C3 7H67 Y l P l 4 C311H42N2Ch C3P H6 5N1C 1 4 C39 H33F E 1 N 1 2 O 3 C39Hb9Y1013 C41 ti481120R C41 H64O13 C43 H43 N7C7 S 2
--

LOGP OCT 2.82 3.72 1.19 EMPIRICAL FORMULA NAME V I N C R I S T I N E SULFATE lPKA= 5 . 5 ) l N C S 6 7 5 7 4 ) VPNCALEUKOBLASTINE SULFATE IPKA= 5 . 4 ) 1 4 9 8 4 2 ) G R A M I C I D I N S-A BACITRACIN A INSULIN POLYPETIN A
NO. 5801 5802 58C3 5804 58C5 58C6
SOLVENT OCTANOL OCTANOL SEC-BUTANOL SEC-BUTANOL SEC-BUTANOL SEC-BUTANOL
REF FOOT NOTE 221 227 84 84 84 84
LOGP SOLV 2.82 3.72 1.21 -0.07 -1.08 0.51
= =
19 19 19 19
-0.63
-2.28 0.21
C46H56N401O.H2S104 C46H58N409.H2S104 CbOH92N12010 C66H103N17016Sl C999 C999
= 0.04; intramolecular H 1 pH 1.1, 37. At pH = PI net charge = zero. In n-pentyl acetate. Calculated log Penal = 1.48; log &to bonds indicated. 5 P reported constant between pH 2 and 6. No log Pactvalues were calculated because the H-bonding capabilities of boronic acids were greatly influenced by the u constant of substituents. pH 2.0. The large difference between the 3 and 4 isomers is explained in ref 478. 9 Compounds with active hydrogens show unusually high 10gPbenzenevalues. At pH 7.4 plus hexadecylamine; the addition compound is also partitioning. l 1 Some lactone also present. l 2 This value appears out of line; it was not used in the regression equation. l 3 P u n - i o n i z e d = P*/(1 where a = degree of dissociation calculated from pK,. l 4 pH 7.4 phosphate buffer; not ion-corrected. pH 3.5. 16 pH -1.0, 17 Apparent P reported; not buffered or ion-corrected. pH 7.05 octadecylamine; addition compound is also partitioning. 19 pH 1.0 using HCI. 2o pH -0.22 using HCl. 2 1 pH 7.1 octadecylamine; addition compound also partitioning. 2 2 Value is ratio of solubilities, not a true P, but the activity of an inert gas is nearly unity even at saturation. 2 3 pH 7.3; ion-corrected 2 4 pH 7.3; estimated pK, = 4.9; absolute values not very reliable but comparison within series valid. 26 Corrected for ionization and dimerization by method of ref 29. 26 Approximate value. 27 pH 7.3 in ref 489; pH 7.0 in ref 206; both ion-corrected. 28 pH 6.3, ion-corrected. 28 pH 5.9. 30 pH 6.9. 3 1 pH 7.4; ion-corrected from pK.. Absolute values not reliable, but comparison within series valid. 3 2 pH 5.4. 3 3 pH 7.8. 3 4 pH 6.0. 36 pH 7.1. 38 pH 6.5 using 1 M phosphate buffer; method = countercurrent extraction. 37 pH 7.1 using 0.1 M phosphate 1 M NaCI. 38 pH 6.6 1 M phosphate. 39 pH 6.9 using phosphate buffer. 40 pH 5.6 using phosphate buffer; ref 504 also lists values at pH 2.1-8.5. 4 1 This reference also lists values for decyl, undecyl, and dodecyl ion pairs. 4 2 May be dimerized in organic phase. 4 3 pH 7.5 0.2 Mphosphate. 4 4 pH 7.4 using phosphate buffer, ion-corrected. 4 6 Calculated from the mole fraction partition coefficient (PMF) the expression P = (PxF) 18(do)/MW,, by X and from where do = density of organic solvent and MW, = its molecular weight. 46 Ion pair. 47 Calculated from ratio Cw/(Co)l/z the Kdimer ref 139. 4 8 At isoelectric point, pH 5.35. 4 9 pH 5.8; ion-corrected using pK. = 4.8. 50 Classification by regression equation appears anomalous. 6 1 0. E 2 Aqueous phase is 5 % HCl. 5 3 In plastic containers. In alkylpyridinium series, adsorbtion to glass gives values lower by 0.15 (decyl), 0.3 (hexyl), and 0.8 (butyl). 5 4 Dissolved in HCl, adjusted to pH 6.5. 5 6 Subject of U. S . Patent 3,417,077 issued to Eli Lilly & Co. 5 6 pH 4.0. 57 pH 8.0 using 0.02 M phosphate-citrate buffer. 58 Assay procedure: J . A g r . Food Chem., 8, 460 (1960). 59 Commercial material: 96% pure. pH 11 using Sorensons buffer. pH 4.7; log P* = -2.00 at pH 2.2. B z Calculated as log P = (pi5 2) - pK.. 6 3 pH 6.4, ion= corrected. Log Ps calculated from ir values listed and log P C H C I ~ 1.40 and log Po,$= -0.70 for sulfanilamide. 6 4 pH 5 . 5 ; phosphate buffer; largely as anion; some polymer possible. G 5 pH 7.4 using phosphate buffer; not ion-corrected. 66 pH 8.93 using carbonate buffer; ioncorrected. 67 pH 9.2 using carbonate-bicarbonate buffer; ion-corrected. 68 pH 1.0; approximately half of phenothiazine ring nitrogens protonated. 69 pH 7.6; where solute has two alkyl N atoms, some diprotonation probable. Entered twice: once as enol, once as keto tautomer. j 1 pH 12.8; not ion-corrected; -0.0001 in neutral form. 7 2 pH 7.32; not ion-corrected; ~ 0 . 1 in neutral form. 7 3 pH 10.15 using carbonate-bicarbonate buffer. 7 4 pH 13.7; not ion-corrected; -0.01 % in neutral form. 75 pK, measured in acetonitrile which accentuates base strength. 77 Log P at infinite dilution calculated by regression analysis; s = 0.03, r = 0.995. Note: mixed solvent 81 is 67 % (by volume) ethyl ether and 33 petroleum ether.
~~
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~I
~~ ~
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Chemical Reviews

Volume 71, Number 6 December 1971