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Quantum similarity approach to LFER: substituent and solvent effects on the acidities of carboxylic acids
Author(s) -
Ponec Robert,
Amat Lluís,
CarbóDorca Ramon
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199906)12:6<447::aid-poc143>3.0.co;2-7
Subject(s) - chemistry , substituent , taft equation , dissociation constant , computational chemistry , dissociation (chemistry) , carboxylic acid , quantum chemical , acid dissociation constant , solvent , organic chemistry , molecule , aqueous solution , biochemistry , receptor
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.