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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)25-37
Number of pages13
JournalJournal of the Serbian Chemical Society
Volume82
Issue number1
DOIs
Publication statusPublished - 2017

Keywords

  • Cimetidine
  • DFTs
  • Fukui
  • HSAB
  • Reactivity

ASJC Scopus subject areas

  • Chemistry(all)

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