Journal of the American Chemical Society

Transition-state effects in the divalent metal ion catalyzed hydrolysis of esters. Hydrolysis of 2-pyridylmethyl hydrogen phthalate

TH Fife, TJ Przystas

Index: Fife, Thomas H.; Przystas, Theodore J. Journal of the American Chemical Society, 1980 , vol. 102, # 24 p. 7297 - 7300

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Citation Number: 19

Abstract

Abstract: Rate constants have been obtained for hydrolysis of 2-pyridylmethyl hydrogen phthalate, an ester with a poor leaving group, at 90 OC in the pH range 6-1 1. The pH-rate constant profile shows hydroxide ion catalysis at high pH and a plateau due to nucleophilic carboxyl group participation. Divalent metal ions (NiZ+, Cozt, ZnZ+) exert a large catalytic effect, although binding to the substrate is weak. Saturation effects were not observed ...