The reaction of the dodecyl(2-hydroxyimidophenethyl)dimethylammonium bromide(DHDB) and N-methylmyristohydroxamate (MMHA) anion with p-nitrophenyl acetate was studied mostly in the presence of aqueous nonionic micelles. Addition of a hydrophobic ammonium ion, TMAG, considerably enhanced the reactivity of MMHA but not that of DHDB (a zwitterion). The rate enhancement for MMHA-TMAC and DHDB in nonionic micelles were almost comparable to those in cationic(CTAB) micelles. It was proposed that the large enhancement observed for some anionic nucleophiles in cationic micelles is to a great extent caused by the formation of hydrophobic, desolvated ion pairs.
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Kunitake et al. (1976) studied this question.
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