The effects of single- and twin-tailed ionic surfactants upon aromatic nucleophilic substitution

Reactions of OH– with 2,4-dinitro-1-chloro-benzene and -naphthalene have been examined in solutions of didodecyldimethylammonium chloride and hydroxide. Rate effects were analysed quantitatively in terms of distribution of reactants between water and the colloidal particles. Second-order rate constants at the surface of the particles are very similar to those in normal aqueous micelles of cetyltrimethylammonium hydroxide, chloride, and bromide and p-octyloxybenzyltrimethylammonium bromide and are slightly higher than in water. Similar observations were made on the reaction of OH– with 2,4-dinitro-1-fluorobenzene.