Nucleophilic aromatic substitution in solutions of cationic bolaform surfactants

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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.

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