Secondary Deuterium Isotope Effects for Enolization Reactions

…, K Haley, R Kanski, CJ Murray, J Pranata

Index: Alston II, William C.; Haley, Kari; Kanski, Ryszard; Murray, Christopher J.; Pranata, Julianto Journal of the American Chemical Society, 1996 , vol. 118, # 28 p. 6562 - 6569

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Citation Number: 21

Abstract

Secondary α-and β-deuterium isotope effects for enolization reactions and equilibria have been determined by ab initio calculations, 1H NMR spectroscopy, and triton exchange kinetics. Kinetic and equilibrium α-deuterium isotope effects for hydroxide ion-catalyzed enolization of acetaldehyde calculated by ab initio methods are normal and depend on the orientation of the secondary hydrogen with respect to the carbonyl group. The computed ...

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