A Theoretical Study of the Enol Contents of Cyclohexanone, Cyclopentanone and Acetone
Ashraf M. Al-Msiedeen *
Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O.Box 179, Tafila 66110, Jordan
Ghassab M. Al-Mazaideh
Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O.Box 179, Tafila 66110, Jordan
Salim M. Khalil
Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O.Box 179, Tafila 66110, Jordan
*Author to whom correspondence should be addressed.
Abstract
PM3 and DFT calculations have been performed with complete optimization of geometries on cyclohexanone, cyclopentanone, and acetone. The enol content trend determined in this work was cyclohexanone > cyclopentanone > acetone, which was found to agree with published experimental and theoretical works. Equilibrium constants, strain energies of enols, and electron distributions are reported.
Keywords: Keto – Enol tautomerism, PM3, DFT, cycloakanones and acetone