Abstract
Cyclization of 2-((3-halopropyl)oxy)phenoxide ion (halo = Br, I; PhBr7 and PhI7, respectively) in micelles is a model for SN2 reactions of nucleophilic anions at micelle−water interfaces. Sulfobetaine micelles of dodecyldimethylammoniopropanesulfonate (C12H25N+(CH3)2(CH2)3SO3-, SB3-12) modestly increase rates of cyclization of PhBr7 and PhI7, and the effect is larger for the latter. The relative rate constants kI/kBr are indicators of medium polarity and their values indicate that the surface polarity of micellized SB3-12 is slightly lower than that of a trimethylammonium micelle and significantly lower than that of water. Changes in 1H chemical shifts of SB3-12 show that the micellar rate effects are not due to changes in micellar structure. Nonionic micelles of polyoxyethylene(23) dodecyl ether (C12H25(OCH2CH2)23OH, Brij 35) modestly speed up cyclization, but reaction appears to be in the water-rich palisade layer of the micelle in conditions such that the distinction between aqueous and micellar pseudo...
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