Nucleophilic aromatic substitution in solutions of cationic bolaform surfactants

Abstract

Reactions of OH^– with 2,4-dinitro-1-chloro-benzene and -naphthalene have been examined in solutions of the following bolaform surfactants: alkane-α,ω-bis(trimethylammonium bromide), alkane = docosane, hexadecane, and dodecane, [bolaform(22)Br, bolaform(16)Br, and bolaform(12)Br], bolaform(22)OH, and bolaform(16)OH. Rate effects of bolaform(22)Br and OH^– were analysed quantitatively in terms of distribution of reactants between water and micelles and second-order rate constants at the micellar surfaces were very similar to those found with normal hexadecyltrimethylammonium micelles. Rate effects were much smaller with bolaform(16)Br and OH^– but were typical of micellar rate enhancements, and bolaform (12)Br had even smaller effects.