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Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH− in Dimeric Micellar Solutions
Department of Physical Chemistry, University of Seville, C/ Profesor García González 1, 41012 Seville, Spain
* Author to whom correspondence should be addressed.
Received: 13 October 2011; in revised form: 31 October 2011 / Accepted: 8 November 2011 / Published: 11 November 2011
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.
Keywords: 2-(p-nitrophenyl)ethyl bromide; basic dehydrobromination; dimeric surfactants; morphological transitions; ion-exchange model
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Graciani, M.M.; Rodríguez, A.; Martín, V.I.; Moyá, M.L. Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH− in Dimeric Micellar Solutions. Molecules 2011, 16, 9467-9479.
Graciani MM, Rodríguez A, Martín VI, Moyá ML. Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH− in Dimeric Micellar Solutions. Molecules. 2011; 16(11):9467-9479.
Graciani, María del Mar; Rodríguez, Amalia; Martín, Victoria I.; Moyá, María Luisa. 2011. "Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH− in Dimeric Micellar Solutions." Molecules 16, no. 11: 9467-9479.