Abstract
The reaction of 2-phenoxyquinoxaline (1) with hydroxide ion is accelerated by reactive counter-ion micelles of cetyltrialkylammonium hydroxides (alkyl=Me, Et, n-Pr, and n-Bu), cetylmethylpiperidinium hydroxide, and cetylquinuclidinium hydroxide containing bulky head groups. First-order rate constants for reaction of (1) with OH− increase with increasing bulk of the head group and are associated with an increase in nucleophile reactivity as water is squeezed away from the micelle surface. Micellar effects upon the alkaline hydrolysis of compound (1) were analyzed by using a model that describes micelle-ion interactions in terms of Langmuir isotherms. © 1998 John Wiley & Sons, Inc. Int J Chem Kinet 30: 777–783, 1998
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