Journal of the American Chemical Society

Acidity and tautomerism of. beta.-keto esters and amides in aqueous solution

JW Bunting, JP Kanter

Index: Bunting, John W.; Kanter, James P. Journal of the American Chemical Society, 1993 , vol. 115, # 25 p. 11705 - 11715

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Citation Number: 41

Abstract

Abstract: The pH-rate profiles for the keto-enol tautomerization of 17@-keto esters and amides (RCOCHzCOX: R= methyl; phenyl; 2-, 3-, and 4-pyridyl; 3 (and 4)-(N- methylpyridinio); X= OCH3, OC2H5, NH2, or N (CH&) have been measured by stopped-flow spectrophotometry in aqueous solution (ionic strength 0.1, 25" C) over the range pH= 2-12. Analysis of these profiles gives the microscopic rate constants for ketonization and ...

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