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The use of atomic charges and orbital energies as hydrogen-bonding-donor parameters for QSAR studies: comparison of MNDO, AM1 and PM3 methods
journal contribution
posted on 2023-06-09, 03:27 authored by Taravat Ghafourian, J C DeardenHydrogen-bonding, important in drug-receptor interactions, also determines the solubility and partitioning of drugs between phases. It is, therefore, important to incorporate the effects of hydrogen-bonding in studies of quantitative structure-activity relationships (QSAR). In this study the atomic charge on the most positively charged hydrogen atom in a molecule and the energy of the lowest unoccupied molecular orbital (LUMO) have been used as a measure of hydrogen-bond-donor capacity. For several hydrogen-bonding acids the Mulliken atomic charges and the energy of the LUMO produced by use of three semi-empirical methods, AM1, PM3 and MNDO, and MNDO electrostatic-potential-derived atomic charges, have been compared in correlations with solvatochromic hydrogen-bonding acidity (Σα2(H)). Atomic charges and LUMO energies, particularly those calculated by use of the AM1 and MNDO methods, were found to correlate well with Σα2(H). They were also found to be good models of hydrogen-bonding in QSAR correlations.
History
Publication status
- Published
Journal
Journal of Pharmacy and PharmacologyISSN
0022-3573Publisher
Royal Pharmaceutical Society of Great Britain / WileyExternal DOI
Issue
6Volume
52Page range
603-610Department affiliated with
- Biochemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2017-11-23Usage metrics
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