The reaction of some nuclear substituted acyclic conjugated styryl ketones and related Mannich bases with ethanethiol

Abstract

The second order rate constants for the reaction of ethanethiol with a number of conjugated nuclear-substituted styryl ketones and related Mannich bases in 50% aqueous acetonitrile was undertaken. Variation of the alkyl group adjacent to the carbonyl function was accompanied by altered avidity to ethanethiol which was explained as being due in part to the varying inductive effects of the alkyl groups which would, in turn, affect the stability of the reaction intermediates. The greatest disparity in reactivity between groups of compounds was between the ketones and analogous Mannich bases which was in accord with the marked difference in bioactivities between these two groups of compounds.