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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Fecha
2017
Autores
Huizar, Luis Humberto Mendoza
Salgado-Morán, Guillermo
Cardona-Villada, Wilson
Pacheco, Alison Geraldo
Glossman-Mitnik, Daniel
Profesor/a Guía
Facultad/escuela
Idioma
en
Título de la revista
ISSN de la revista
Título del volumen
Editor
Serbian Chemical Society
Nombre de Curso
Licencia CC
CC BY 4.0
Código legal
Licencia CC
https://creativecommons.org/licenses/by/4.0/legalcode.es
Resumen
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.
Notas
Indexación: Scopus
Palabras clave
Cimetidine, DFTs, Fukui, HSAB, Reactivity
Citación
Journal of the Serbian Chemical Society Volume 82, Issue 1, Pages 25 - 372017
DOI
10.2298/JSC160512077M