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

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 aqu...

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Published inJournal of the Serbian Chemical Society Vol. 82; no. 1; p. 25
Main Authors Mendoza-Huizar, Luis Humberto, Salgado-Morán, Guillermo, Wilson Cardona-Villada, Alison Geraldo Pacheco, Daniel Glossman-Mitnik
Format Journal Article
LanguageEnglish
Published Belgrade Journal of the Serbian Chemical Society 01.01.2017
Subjects
Chemical attack
Cimetidine
Free radicals
Nucleophiles
Reactivity
Solvents
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Summary: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.
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC160512077M