Journal of Physical Chemistry p. 11494 - 11500 (1995)
Update date:2022-08-16
Topics:
Frescura, Vera L. A.
Marconi, Dilma M. O.
Zanette, Dino
Nome, Faruk
Blasko, Andrei
Bunton, Clifford A.
Fractional micellar ionization, α, and micelle concentrations have been measured for mixed micelles of sodium dodecanoate (SDOD) and sulfobetaines (CnH2n+1N+Me2(CH2)3SO3-, SB3-n, n = 10, 12, 14, 16), and values of pHapp have been calculated from deprotonation of 1-dodecylpyridinium-4-aldoxime bromide.For 0.1 M total surfactant first-order rate constants of hydrolyses of 2,4-dinitrophenyl acetate and octanoate (DNPA and DNPO, respectively) and benzoic anhydride (Bz2O) go through maxima at a mole fraction of SDOD of ca. 0.5 for DNPA and DNPO and 0.8 for Bz2O.These rate maxima are fitted quantitatively in terms of reactions of OH- and dodecanoate ion on the assumption that sulfobetaine micelles increase the nucleophilicity of the carboxylate ion.This rate effect is ascribed to decreased hydration and ion-pairing of the dodecanoate ion in the mixed micelles, on the basis of 1H NMR spectrometry in mixtures of SDOD and SB3-14.Therefore, incorporation of dodecanoate ion in SB3-n slows reaction by "dilution" in the micelle, but this inhibition is offset by activation of the nucleophilic dodecanoate ion.
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