Solvent effect in the reaction of n-sulphonilsulphilimines with benzenethiol

Article abstract of DOI:10.1016/S0040-4020(01)97700-2

Rate coefficients for the reactions of S,S-dimethyl-, S-methyl-S-phenyl- and S,S-diphenyl-N-tosylsulphilimine with benzenethiol in various alcohols have been determined at different temperatures. Multiparametric equations, involving specific and non-specific solute-solvent interactions, have been used to interpret quantitatively the data. The results on the solvent effect and the activation parameters indicate that the reactions proceed through the rate-determining formation of a thiol-sulphilimine adduct which occurs most likely through a cyclic transition state involving one molecule of thiol, one of sulphilimine, and one of alcohol.