Journal of the American Chemical Society

Generation and stability of a simple thiol ester enolate in aqueous solution

TL Amyes, JP Richard

Index: Amyes, Tina L.; Richard, John P. Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10297 - 10302

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Citation Number: 127

Abstract

Abstract: The exchange for deuterium of the a-protons of ethyl thioacetate and of acetone in 3-quinuclidinone buffers in D20 at 25 OC and pD= 7.7-9.3 was followed by'H NMR spectroscopy. The exchange reactions lead to the appearance of signals due to the a-CH2D and a-CHD2 species that are cleanly resolved from each other and from the signal due to the a-CH3 species. Observed rate constants for the 3-quinuclidinone-catalyzed exchange ...