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Use of electron densities in comparative molecular field analysis (CoMFA): OH bond dissociation energies in phenols
Author(s) -
Vaz Roy J.,
Edwards Michael,
Shen Jian,
Pearlstein Robert,
Kominos Dorothea
Publication year - 1999
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/(sici)1097-461x(1999)75:3<187::aid-qua8>3.0.co;2-c
Subject(s) - chemistry , computational chemistry , dissociation (chemistry) , bond dissociation energy , quantitative structure–activity relationship , ab initio , phenol , electron density , basis set , ground state , density functional theory , singlet state , electron , stereochemistry , organic chemistry , atomic physics , excited state , physics , quantum mechanics
The ability to successfully predict the bond dissociation energies of the phenol OH bond is important in medicinal chemistry for a variety of therapeutic applications. Previous reports utilized rigorous approaches with semi‐empirical, ab initio and density functional theory, as well as more empirically based quantitative structure activity relationship (QSAR) approaches. Here we report the use of a three‐dimensional quantitative structure activity relationship method incorporating electron densities computed using the Austin Method 1 (AM1) method followed by correlation of the electron density with the relative bond dissociation energies. The QSAR is determined for both the ground‐state phenol as well as the singlet phenoxy radical with a set of compounds for which the bond dissociation energies have been measured. The model developed using the ground‐state phenol model is more predictive. The coefficients of the QSAR have also been interpreted. ©1999 John Wiley & Sons, Inc. Int J Quant Chem 75: 187–195, 1999