The mechanism of reaction of phosphoramidate monoanions with nucleophiles

Abstract

The kinetics of reaction of the N-(4-chlorophenyl)phosphoramidate monoanion in hydroxylamine buffer require an intermediate common to hydrolysis and hydroxylaminolysis. The intermediate is possibly an induced-dipole pair analogous to the ion pairs suggested for substitution at saturated carbon. The same type of intermediate may be a feature of the reactions of all phosphoramidate monoanions and of phosphate monoester monoanions and dianions.