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A Thermodynamic Study of Ketoreductase-Catalyzed Reactions, Part 3: Reduction of 1-Phenyl-1-Alkanones in Non-Aqueous Solvents

Published

Author(s)

Yadu D. Tewari, N Kishore, J D. Rozzell, David J. Vanderah, Michele M. Schantz

Abstract

The equilibrium constants K for the reactions (1-phenyl-1-alkanone + 2-propanol = 1-phenyl-1-alkanol + acetone) in the solvents n-pentane and n-hexane have been determined by using gas chromatography at the temperature T = 298.15 K. The 1-phenyl-1-alkaones included in this study were: 1-phenyl-1-ethanone, 1-phenyl-1-propanone, 1-phenyl-1-butanone, 1-phenyl-1-pentanone, 1-phenyl-1-hexanone and 1-phenyl-1-heptanone. The equilibrium constants for the reaction involving 1-phenyl-1-ethanone were measured in the solvent n-hexane as a function of temperature (T = 288 K to T = 308 K). The calculated thermodynamic quantities for the 1-phenyl -1-ethanone reaction at T = 298.15 K are: K = 0.2177 0.0018; the standard molar Gibbs free energy change, DrG m = (3.78 0.02) kJ mol-1; the standard molar enthalpy change, DrH m = (4.53 0.87) kJ mol-1, and the standard molar entropy change, DrS m= (2.5 2.9) J K?1 mol-1. The equilibrium constants of 1-phenyl-1-alkanone with an odd number of carbons in alkyl side chain are higher than the equilibrium constants of the preceding 1-phenyl-1-alkanone having an even number of carbons in the side chain and follow a zig-zag pattern with increasing carbon number in the alkyl side chain.
Citation
Journal of Chemical Thermodynamics
Volume
38
Issue
10

Keywords

1-phenyl-1-alkanone, 1-phenyl-1alkanol, 2-Propanol, acetone, Equilibrium Constant, Ketoreductase, thermodynamics

Citation

Tewari, Y. , Kishore, N. , Rozzell, J. , Vanderah, D. and Schantz, M. (2006), A Thermodynamic Study of Ketoreductase-Catalyzed Reactions, Part 3: Reduction of 1-Phenyl-1-Alkanones in Non-Aqueous Solvents, Journal of Chemical Thermodynamics (Accessed April 20, 2024)
Created September 30, 2006, Updated October 12, 2021