The Hammett equation and micellar effects on SN2 reactions of methyl benzenesulfonates - The role of micellar polarity

Abstract

Substituent effects on the reaction of H2O, OH-, and Br- with p-substituted methyl benzenesulfonates in cationic micelles of cetyl trialkylammonium ion surfactants (n-C16H33NR3X, X = OH, Br, R = Me, Et, nPr, nBu) and in water were analyzed by using the Hammett equation. Values of p in the various media confirm that micellar interfacial regions are less polar than water and polarities decrease with increasing bulk of the surfactant head-group. © Wiley-VCH Verlag GmbH, 2000.