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

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Luis Humberto Mendoza-Huizar
http://orcid.org/0000-0003-2373-4624
Guillermo Salgado-Morán
Wilson Cardona-Villada
Alison Geraldo Pacheco
Daniel Glossman-Mitnik

Abstract

In the present work, the chemical reactivity of cimetidine A, C and D in different solvents was analyzed 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. However, 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. In addition, the results suggested that CimC and CimD are better nucleophiles that CimA. The values of the Fukui function 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 attack are located on the thioether sulfur. For CimD, the number and place of the electrophilic and free radical sites are independent of the solvent.

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How to Cite
[1]
L. H. Mendoza-Huizar, G. Salgado-Morán, W. Cardona-Villada, A. G. Pacheco, and D. Glossman-Mitnik, “A DFT study of the chemical reactivity of cimetidine A, C and D in the gas phase and in H2O, MeOH and EtOH solvents”, J. Serb. Chem. Soc., vol. 82, no. 1, pp. 25–37, Feb. 2017.
Section
Theoretical Chemistry
Author Biographies

Luis Humberto Mendoza-Huizar, Universidad Autónoma del Estado de Hidalgo, Academic Area of Chemistry, Carretera Pachuca-Tulancingo Km. 4.5 Mineral de la Reforma, Hgo

Academic Area of Chemistry, Researcher

Guillermo Salgado-Morán, Universidad Andrés Bello. Departamento de Ciencias Químicas, Facultad de Ciencias Exactas. Sede Concepción. Autopista Concepción-Talcahuano 7100, Talcahuano

Departamento de Ciencias Químicas, Researcher

Wilson Cardona-Villada, Universidad Andrés Bello. Departamento de Ciencias Químicas, Facultad de Ciencias Exactas. Sede Concepción. Autopista Concepción-Talcahuano 7100, Talcahuano

Departamento de Ciencias Químicas, Researcher

Alison Geraldo Pacheco, Instituto Federal de Educação Ciência e Tecnologia do Sul de Minas Gerais, Inconfidentes, Minas Gerais

Instituto Federal de Educação Ciência e Tecnologia, Researcher

Daniel Glossman-Mitnik, Laboratorio Virtual NANOCOSMOS, Centro de Investigación en Materiales Avanzados, Chihuahua, Miguel de Cervantes 120, Complejo Industrial Chihuahua, Chih 31136 and Departament de Química, Universitat de les Illes Balears, 07122 Palma de Mallorca, Spain

Laboratorio Virtual NANOCOSMOS, Researcher

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