Abstract

The specific rates of solvolysis of benzenesulfonyl chloride and three 4-substituted derivatives can be very well correlated using the extended Grunwald-Winstein equation, with incorporation of NT solvent nucleophilicity and YCl solvent ionizing power values. In two instances, it was shown that almost identical correlations were obtained after the incorporation of methyl groups into the 2- and 6-positions of the benzene ring. No evidence was found for a dissociative (SN1) mechanism or for a duality of mechanism. All of the results can be rationalized in terms of a concerted bimolecular displacement (SN2) mechanism, involving attack by solvent at sulfur.

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