Dephosphorylation in functional micelles. The role of the imidazole group

JM Brown, CA Bunton, S Diaz…

Index: Brown, John M.; Bunton, Clifford A.; Diaz, Simon; Ihara, Yasuji Journal of Organic Chemistry, 1980 , vol. 45, # 21 p. 4169 - 4174

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Citation Number: 24

Abstract

Dephosphorylation of p-nitrophenyl diphenyl phosphate (p-NPDPP) is effectively catalyzed by micelles of [5-[(cr-N-~-histidinyl methyl ester) carbonyl] n-heptadecylltrimethylammonium chloride (1) and dimethylhexa-decyl [(4-imidazolyl) methyl] a" onium chloride (2) by factors of 95 and 400, respectively, at pH ca. 8. The kinetic solvent-deuterium isotope effects kH20/kD20 of 2-2.8 are consistent with imidazole moieties of the surfactants acting as ...