1,2-Dipolar addition model for the cytoprotective activity of selected α,β-unsaturated compounds with C=O functionality: An ab initio study

Abstract

The mechanism of the addition of a nucleophile (an alkylthiol group) to a double bond of α,β-unsaturated systems in the gas phase was explored. In this study, intermediates of the reaction were also investigated using ab initio calculations (RHF/6-31G* and MP2/6-31+G*). Our results indicate that direct dipolar attack of the S-H group of an alkylthiol on the C=C double bond is a reasonable reaction path. The present results represent, therefore, additional support for our hypothesis. This suggests that the mechanism of cytoprotection might be mediated, at least in part, by a reaction between the olefinic acceptor and the sulfhydryl-containing groups of the mucosa.