Intrinsic acidities of meta- and para-substituted phenols from calculated molecular properties

Abstract

Intrinsic acidities of monosubstituted phenols have been calculated from a relationship obtained by comparing experimental data and energy differences between neutral molecules and the corresponding anions, calculated using the INDO method. Other calculated molecular properties (ionization potential of the anion, electric charge on the acidic hydrogen in the neutral molecule) have also been used, yielding values of the intrinsic acidity well within experimental errors. Ab initio calculations have been carried out on some systems which showed a difference between their predicted and experimental intrinsic acidities.