1,2-Dipolar addition model for the cytoprotective activity of selected a,b-unsaturated compounds with CyO functionality: an ab initio study

M.ZAMORA; A.M.RODRIGUEZ; F.D.SUVIRE; E.A.JAUREGUI; F.TOMAS VERT; ENRIZ R.D.

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2001 vol. 538 p. 225 - 233

0166-1280

The mechanism of the addition of a nucleophile (an alkylthiol group) to a double bond of a,b-unsaturated systems in the gas phase was explored. In this study, intermediates of the reaction were also investigated using ab initio calculations (RHF/6-31Gp and MP2/6-311Gp). Our results indicate that direct dipolar attack of the S±H group of an alkylthiol on the CyC 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 ole®nic acceptor and the sulfhydrylcontaining groups of the mucosa.