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Quantum similarity approach to LFER: Substituent and solvent effects on the acidities of carboxylic acids

Abstract:

Quantum similarity measures were used to estimate dissociation constants for acid-base equilibria. It is proposed that the dissociation constant of a carboxylic acid may be described by the electronic density function of the COOH group and quantified by the self-similarity measure of this fragment. In addition, using a polarized continuum model, the inclusion of surrounding medium effects on the electronic density function of the solute is easily taken into account, and in this way the solvent effect on acid dissociation constants can be simply described. A successful correlation was obtained between dissociation constants of a variety of acids in different solvents and quantum self-similarity measures of the COOH fragment. Copyright © 1999 John Wiley & Sons, Ltd.