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A DFT study of the chemical reactivity of cimetidine A, C and D in the gas, H2O, MeOH and EtOH solvents

Mendoza Huizar Luis Humberto (Universidad Autónoma del Estado de Hidalgo, Academic Area of Chemistry, Carretera Pachuca-Tulancingo Km. Mineral de la Reforma, Hgo, México)
Salgado-Morán Guillermo (Universidad Andrés Bello, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Sede Concepción, Autopista Concepción-Talcahuano, Talcahuano, Chile)
Cardona-Villada Wilson (Universidad Andrés Bello, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Sede Concepción, Autopista Concepción-Talcahuano, Talcahuano, Chile)
Pacheco Alison Geraldo (Instituto Federal de Educação Ciência e Tecnologia do Sul de Minas Gerais, Inconfidentes, Minas Gerais, Brasil)
Glossman-Mitnik Daniel (Laboratorio Virtual NANOCOSMOS, Centro de Investigación en Materiales Avanzados, Chihuahua, Miguel de Cervantes, Complejo Industrial Chihuahua, Chih, México + Universitat de les Illes Balears, Departament de Química, Palma de Mallorca, Spain)

% Fukui % DFT s KR nema In the present work, we have analyzed the chemical reactivity of cimetidine A, C and D in different solvents; through the evaluation of global and local DFT reactivity descriptors. In the gas, MeOH and EtOH phases, cimetidine A, C and D exhibit energy differences of 3-11 kcal mol-1. But, in the aqueous phase, cimetidine A and D are approximately isoenergetic. The values of the hardness indicate that cimetidine A, C and D are more reactive in the presence of a solvent than in the gas phase. Also, our results suggest that CimC and CimD are better nucleophiles that CimA. The Fukui Function values suggest that the more reactive sites of CimA are not modified in the different solvents. In the case of CimC, the more reactive sites to electrophilic and free radical attacks are located on the thioether sulfur. For CimD, the number and place of the electrophilic and free radical sites are independent of the solvent.

Keywords: Cimetidine, reactivity, HS