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

• Published in: Journal of molecular structure. Theochem Vol. 538; no. 1; pp. 225 - 233
• Main Authors: Zamora, M.A, Rodrı́guez, A.M, Suvire, F.D, Jáuregui, E.A, Tomás-Vert, F, Enriz, R.D
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 30.03.2001
• Subjects: 1,2-Dipolar addition model; Ab initio calculations; Cytoprotective activity; α,β-Unsaturated compounds; Cytoprotective activity; α,β-Unsaturated compounds; 1,2-Dipolar addition model; Ab initio calculations
• ISSN: 0166-1280; 1872-7999
• DOI: 10.1016/S0166-1280(00)00707-7

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.