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A Thermodynamic Study of Ketoreductase-Catalyzed Reactions. 2. Reduction of Cycloalkanones in Non-Aqueous Solvents



Yadu D. Tewari, Karen W. Phinney, J F. Liebman


The equilibrium constants for the ketoreductase-catalyzed reactions (cycloalkanone + 2-propanol = cycloalkanol + acetone) have been measured inn-hexane, n-pentane, and supercritical carbon dioxide (pressure P = 8.0 to 12.0 MPa). The cycloalkanones included in this study were: cyclobutanone, cyclopentanone, cyclohexanone, cycloheptanone, and cyclooctanone. The equilibrium constants for the reactions involving cyclobutanone and cyclohexanone were measured in n-hexane over the range T = 288.35 K to T = 308.05 K. The thermodynamic quantities at T = 298.15 K are:K = 0.763 0.001; ?rG?m = (0.670 0.002) kJ mol-1; ?rH?m = (1.09 0.11) kJ mol 1, and ?rS?m= -(5.9 0.4) J K-1 mol-1 for the reaction involving cyclobutanone; and K = 15.7 0.2; ?rG?m = (6.82 0.02) kJ mol-1; ?rH?m = (4.6 1.0) kJ mol-1, and ?rS?m= (7.4 3.3) J K-1 mol-1 for the reaction involving cyclohexanone, respectively. An inspection of the equilibrium constants for these reactions in n hexane, n pentane, and SCCO2 shows that solvent dependence is not significant. The equilibrium constants of cycloalkanones decrease with increasing value of the number of carbons, NC with the exception of cyclohexanone. The cyclohexanol, which adopts a tetrahedral conformation around each carbon, is thermodynamically favored and more stable compared to other cycloalkanol rings, and this is reflected in the significantly higher value of theequilibrium constant obtained for this reaction. Comparisons with results obtained by using two independent thermochemical routes are also made.
Journal of Chemical Thermodynamics
No. 4


2-propanol, acetone, cycloalkanol, cycloalkanone, equilibrium constant, ketoreductase, n-hexane, n-pentane, supercritical carbon dioxide


Tewari, Y. , Phinney, K. and Liebman, J. (2006), A Thermodynamic Study of Ketoreductase-Catalyzed Reactions. 2. Reduction of Cycloalkanones in Non-Aqueous Solvents, Journal of Chemical Thermodynamics (Accessed July 17, 2024)


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Created April 1, 2006, Updated February 17, 2017