Polytrifluoromethylation versus polyfluorination of the isomers of Kekule benzene and phenol: a theoretical study

The polyfluorination and polytrifluoromethylation effects on electronic structure and intrinsic acidities are studied by using DFT B3LYP and NBO calculations for the valence isomers of benzene and phenol, that is, the structures of prismane, benzvalene, Kekule and Dewar systems. The isomerization of the benzene derivatives has resulted in cases where the acidities increased when compared to the respective phenol derivatives.