Mechanism of hydrolysis of phosphorylethanolamine diesters. Intramolecular nucleophilic amine participation

Robert A. Lazarus, Patricia Ann Benkovic, Stephen Benkovic

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18 Scopus citations

Abstract

Intramolecular displacement reactions at phosphorus have been examined in a series of N-alkyl-O-arylphosphoryl-ethanolamines in water at 35°C. The examination of the pH-rate profiles and the direct observation by 31P n.m.r. of the reaction products implicate a nucleophilic role for the amine. A rate enhancement of 106-107 is observed. Structure-reactivity correlations derived by changing the pKa of the amine and leaving group yield values for βnuc ≃0.7 and β1g ≃-1.25 and support an uncoupled concerted mechanism. A discussion of the mechanisms of nucleophilic reactions involving amines and oxyanions with inter- and intra-molecular phosphate di- and tri-esters is presented.

Original languageEnglish (US)
Pages (from-to)373-379
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number2
DOIs
StatePublished - Jan 1 1980

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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