Conformations of the methyl and aryl esters of the arylsulfonic acids

Abstract

1. The substituted methylarylsulfonates and arylarylsulfonates exist as mixtures of trans and gauche conformers, the latter predominating at equilibrium (∼70%). 2. The angle of aryl group rotation relative to the Csp3-S-O plane is 43° in the methylphenylsulfonates and the methyl-p-tolylsulfonates and 75° in the methyl-p-bromophenylsulfonates. 3. As a result of electron-acceptor effects from the SO2 group, the S-O-C plane of the arylsulfonic acids esters are almost perpendicular to the aromatic ring. © 1980 Plenum Publishing Corporation.