The reactive species in the hydrolysis of 3-hydroxy-2-pyridylmethyl phosphate are the neutral zwitterion, the monoanion, and the dianion, of which the last speices is the most labile; the intramolecular catalytic effect of the hydroxy-group is much greater than that of the pyridinium group, and causes a unique rate enhancement.
Y. Murakami, J. Sunamoto and H. Ishizu, J. Chem. Soc. D, 1970, 1665 DOI: 10.1039/C29700001665
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