Mechanism of hydrolysis of phosphorylethanolamine triesters. Multiple catalytic effects of an intramolecular amino group

RA Lazarus, SJ Benkovic

Index: Lazarus,R.A.; Benkovic,S.J. Journal of the American Chemical Society, 1979 , vol. 101, p. 4300 - 4312

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Citation Number: 14

Abstract

Abstract: Intramolecular displacement reactions at phosphorus have been examined in a series of N-alkyl-0-(arylphenylphos-phory1) ethanolamines in 45% dioxane-water (v/v) at 35 OC. The examination of the pH-rate profiles, the detection of external buffer catalysis, and the observation of deuterium solvent effects reveal the concurrent operation of three types of P-0 bond cleavage mechanisms: electrostatic catalysis by the protonated ammonium ...