Skip to main content
U.S. flag

An official website of the United States government

Official websites use .gov
A .gov website belongs to an official government organization in the United States.

Secure .gov websites use HTTPS
A lock ( ) or https:// means you’ve safely connected to the .gov website. Share sensitive information only on official, secure websites.

A Thermodynamic Study of Ketoreductase-Catalyzed Reactions, Part 5. Reduction of Substituted Ketones in n-Hexane



Yadu D. Tewari, David J. Vanderah, Michele M. Schantz, Robert N. Goldberg, J D. Rozzell, J F. Liebman, Raymond W. Hui, Yitzy Nissenbaum, Ahmad R. Parniani


The equilibrium constants K for the ketoreductase-catalyzed reduction reactions of 1-benzyl-3-pyrrolidinone, ethyl 2-oxo-4-phenylbutyrate, ethyl 4-chloroacetoacetate, 1-benzyl-4-piperidone, and 1-benzyl-3-piperidone were measured in n-hexane at T = 298.15 K by using gas chromatography. The equilibrium constants for the reaction involving 1-benzyl-4-piperidone were also measured as a function of temperature (288.15 K to 308.05 K). The calculated thermodynamic quantities for the reaction (1-benzyl-4-piperidone + 2-propanol = 1-benzyl-4-hydroxypiperidine + acetone) reaction carried out in n-hexane at T = 298.15 K are: K = (26.2 1.7); DrG m = (8.10 0.16) kJ mol-1; DrH m = (3.44 0.42) kJ mol-1; and DrS m = (15.6 1.4) J K-1 mol-1. The chirality of the hydroxyl products of the reactions (1), (2), (3) and (5) has also been investigated. The results showed that the stereoselectivity of the hydroxyl products formed can be controlled by the selection of the solvent and enzyme used in these reactions. The thermochemical results for these reactions have been compared with the results for reactions that have analogous structural features and with the results of quantum chemical calculations.
Journal of Chemical Thermodynamics


1-benzyl-3-piperidone, 1-benzyl-3-pyrrolidinone, 1-benzyl-4-piperidone, enthalpy, equilibrium constant, ethy 4-chloroacetoacetate, ethyl 2-oxo-4-phenylbutyrate, ketoreducatase


Tewari, Y. , Vanderah, D. , Schantz, M. , Goldberg, R. , Rozzell, J. , Liebman, J. , Hui, R. , Nissenbaum, Y. and Parniani, A. (2008), A Thermodynamic Study of Ketoreductase-Catalyzed Reactions, Part 5. Reduction of Substituted Ketones in n-Hexane, Journal of Chemical Thermodynamics (Accessed July 15, 2024)


If you have any questions about this publication or are having problems accessing it, please contact

Created March 31, 2008, Updated October 12, 2021