Kinetics of the Reaction of Benzenesulfonyl Chloride with Substituted Benzoate Ions in Methanol

Article abstract of DOI:10.1021/jo01312a029

The rate constants and activation parameters for the reaction of benzenesulfonyl chloride with substituted benzoate ions have been measured in methanol.The reaction is second order overall and first order with respect to each reactant.The rate constants are greater with electron-donating substituents while they are lower with electron-withdrawing groups.The substituent effects are correlated by Hammett (ρ -0.35) and Broensted (β 0.35) equations, respectively, and the results compared with the corresponding data for the reaction of benzenesulfonyl chloride with substituted anilines and related reactions.The kinetic results are interpreted in terms of a synchronous direct bimolecular nucleophilic displacement mechanism.