A DFT Study on Stepwise Fluorinated Methylenecyclopentane-1-Methylcyclopentene System

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.