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

Medeiros Michelle | Zendy; Manfredi Alex M. | Zendy; Kirby Anthony J. | Zendy; Nome Faruk | Zendy

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

Author(s) -

Medeiros Michelle,

Manfredi Alex M.,

Kirby Anthony J.,

Nome Faruk

Publication year - 2013

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.3165

Subject(s) - chemistry , hydrolysis , phosphate , leaving group , pyridine , medicinal chemistry , organic chemistry , catalysis

The microscopic p K 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. Copyright © 2013 John Wiley & Sons, Ltd.

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