Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH- in Dimeric Micellar Solutions

Abstract

The dehydrobromination reaction 2-(p-nitrophenyl)ethyl bromide + OH- was investigated in several alkanediyl-a-w-bis(dodecyldimethylammonium) bromide, 12-s-12,2Br- (with s = 2, 3, 4, 5, 6, 8, 10, 12) micellar solutions, in the presence of NaOH 5 × 10-3 M. The kinetic data were quantitatively rationalized within the whole surfactant concentration range by using an equation based on the pseudophase ion-exchange model and taking the variations in the micellar ionization degree caused by the morphological transitions into account. The agreement between the theoretical and the experimental data was good in all the dimeric micellar media studied, except for the 12-2-12,2Br- micellar solutions. In this case, the strong tendency to micellar growth shown by the 12-2-12,2Br- micelles could be responsible for the lack of accordance. Results showed that the dimeric micelles accelerate the reaction more than two orders of magnitude as compared to water.