Deacylation effect in the hydrolysis of p-nitrophenyl esters by bifunctional comicelles containing imidazolyl and hydroxyl groups.
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概要
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The rate constants for hydrolysis of <I>p</I>-nitrophenyl acetate, hexanoate, and dodecanoate catalyzed by bifunctional catalysts containing the imidazolyl and hydroxyl groups have been determined in the presence of hexadecyltrimethylammonium bromide micelles at 25 °C. The kinetic analysis suggests a nucleophilic mechanism which involves acylation followed by deacylation at the imidazolyl group. Although no appreciable differences in cooperative catalytic efficiencies are observed between the bifunctional groups in the acylation step, it is found that the deacylation rates are accelerated by the hydroxyl group of the catalyst in the presence of micelles.
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