Effect of Fluorine Substitution on Phenol Acidities in the Gas Phase and in Aqueous Solution. A Computational Study Using Continuum Solvation Models

Abstract

The effect of fluorine substitution on the gas and aqueous phase acidity of the monofluorophenols has been investigated with a combination of computational techniques. The effects of aqueous solvation were included using the SM2, SM3, and GB/SA continuum solvation models. These solvation models produce calculated free energies of hydration that are in good agreement with the available experimental data and appear to be quite useful for the prediction of the solvent effects on the relative acidities of the fluorophenols with respect to phenol. A thorough analysis of the charge distribution in the gas and aqueous phases provides insight into the nature of the experimentally observed solvent attenuation of substituent effects for these compounds