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
UR - http://www.scopus.com/inward/record.url?scp=85011654053&partnerID=8YFLogxK
U2 - 10.2298/JSC160512077M
DO - 10.2298/JSC160512077M
M3 - Article
AN - SCOPUS:85011654053
VL - 82
SP - 25
EP - 37
JO - Journal of the Serbian Chemical Society
JF - Journal of the Serbian Chemical Society
SN - 0352-5139
IS - 1
ER -