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

Autor:	Faruk Nome, Anthony J. Kirby, Alex M. Manfredi, Michelle Medeiros
Rok vydání:	2013
Předmět:	Organic Chemistry Leaving group chemistry.chemical_element Protomer Phosphate Medicinal chemistry Oxygen chemistry.chemical_compound Hydrolysis chemistry Pyridine Organic chemistry Physical and Theoretical Chemistry Spontaneous hydrolysis
Zdroj:	Journal of Physical Organic Chemistry. 26:1044-1047
ISSN:	0894-3230
DOI:	10.1002/poc.3165
Popis:	The microscopic pKa 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 ROPO3=. 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.
Databáze:	OpenAIRE
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