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Alkaline hydrolysis of 2‐phenoxyquinoxaline in reactive counter‐ion micelles: Effects of head group size
Author(s) -
Cuenca Angela
Publication year - 1998
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/(sici)1097-4601(1998)30:11<777::aid-kin1>3.0.co;2-s
Subject(s) - chemistry , micelle , hydroxide , alkaline hydrolysis , reactivity (psychology) , hydrolysis , ion , nucleophile , reaction rate constant , inorganic chemistry , alkyl , kinetics , organic chemistry , aqueous solution , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics
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