Solvolysis of 2-Phenylethyl Benzenesulfonates in Methanol-Water Mixtures

摘要

Solvolyses of 2-phenylethyl benzenesulfonates have been studied in methanol-water mixtures. Cross interaction constants, ヱYZ, between substituents Y in the substrate and Z in the leaving group indicated somewhat closer distance between the two substituents than expected for the reaction system, which supported the involvment of phenyl group assisted pathway in the solvolysis. A smaller magnitude of ヱYZ for MeOH was interpreted as the enhencement of solvent assisted pathway since MeOH is more nucleophilic than H2O. Other selectivity parameters, Winstein coefficient m, Hammett`s ヱ+Y and ヱZ, as well as activation parameters supported the participation of aryl assisted and aryl unassisted pathways in the SN2 process of the solvolysis reaction.