A DFT Study on Stepwise Fluorinated Methylenecyclopentane ⇌1-Methylcyclopentene System
Ghassab M. Al-Mazaideh *
Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O.Box 179, Tafila 66110, Jordan
Wafa B. Ejlidi
Department of Chemistry, School of Basic Science, Libyan Academy for Graduate Studies, P.O.Box 79031, Tripoli, Libya
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
Density functional theory (DFT) calculations have been performed to calculate the optimized geometries of stepwise fluorinated methylenecyclopentanes and 1-methylcyclopentenes. Increasing the number of fluorine atoms caused a destabilization of methylenecyclopentane. Perfluorinated 1-methylcyclopentene was found to be present in substantial concentration. This is supported by calculations of the Gibbs free energy and isodesmic reactions. These results are compared with fluorinated methyenecyclopropane and the fluorinated cyclopentanones keto-enol systems. Enthalpies, entropies and dipole moments are reported.
Keywords: Fluorinated methylenecyclopentane, tautomerism, DFT