The spontaneous hydrolysis of 2-pyridyl phosphate is a good model for the special mechanism for the hydrolysis of phosphate monoester monoanions

摘要

The microscopic pK_a of the pyridine N of the phosphate monoester 2-pyridyl phosphate (MPP) is 2.76, significantly higher than that expected for the leaving group (RO) oxygen of a typical monoester ROPO_3~=. This favours the prototropic equilibrium considered to be the key step in the rapid hydrolysis of a typical monoester, and the observed rate of hydrolysis of the monoanion MPP~- is shown to be close to that expected for the protomer MPP~(+=), with neutral 2-pyridone as the leaving group.