Use of electron densities in comparative molecular field analysis (CoMFA): OH bond dissociation energies in phenols
✍ Scribed by Roy J. Vaz; Michael Edwards; Jian Shen; Robert Pearlstein; Dorothea Kominos
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 252 KB
- Volume
- 75
- Category
- Article
- ISSN
- 0020-7608
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✦ Synopsis
The ability to successfully predict the bond dissociation energies of the phenol O᎐H 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 Ž . activity relationship QSAR approaches. Here we report the use of a three-dimensional quantitative structure activity relationship method incorporating electron densities Ž . 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.