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

Luis Humberto Mendoza Huizar, Guillermo Salgado-Morán, Wilson Cardona-Villada, Alison Geraldo Pacheco, Daniel Glossman-Mitnik

Resultado de la investigación: Article

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.

Idioma originalEnglish
Páginas (desde-hasta)25-37
Número de páginas13
PublicaciónJournal of the Serbian Chemical Society
Volumen82
N.º1
DOI
EstadoPublished - 2017

Huella dactilar

Chemical reactivity
Cimetidine
Discrete Fourier transforms
Gases
Free Radicals
Nucleophiles
Sulfides
Sulfur
Hardness

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

Huizar, Luis Humberto Mendoza ; Salgado-Morán, Guillermo ; Cardona-Villada, Wilson ; Pacheco, Alison Geraldo ; Glossman-Mitnik, Daniel. / A DFT study of the chemical reactivity of cimetidine A, C and D in the gas phase and in H2O, MeOH and EtOH solvents. En: Journal of the Serbian Chemical Society. 2017 ; Vol. 82, N.º 1. pp. 25-37.
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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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A DFT study of the chemical reactivity of cimetidine A, C and D in the gas phase and in H2O, MeOH and EtOH solvents. / Huizar, Luis Humberto Mendoza; Salgado-Morán, Guillermo; Cardona-Villada, Wilson; Pacheco, Alison Geraldo; Glossman-Mitnik, Daniel.

En: Journal of the Serbian Chemical Society, Vol. 82, N.º 1, 2017, p. 25-37.

Resultado de la investigación: Article

TY - JOUR

T1 - A DFT study of the chemical reactivity of cimetidine A, C and D in the gas phase and in H2O, MeOH and EtOH solvents

AU - Huizar, Luis Humberto Mendoza

AU - Salgado-Morán, Guillermo

AU - Cardona-Villada, Wilson

AU - Pacheco, Alison Geraldo

AU - Glossman-Mitnik, Daniel

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - Cimetidine

KW - DFTs

KW - Fukui

KW - HSAB

KW - Reactivity

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