Hydroxyl stretching in substituted phenols: An AM1 study
Article first published online: 19 OCT 2004
Copyright © 1993 John Wiley & Sons, Inc.
International Journal of Quantum Chemistry
Supplement: Proceedings of the International Syposium on the Application of Fundamental Theory to Problems of Biology and Pharmacology
Volume 48, Issue Supplement 20, pages 7–15, 13/20 March 1993
How to Cite
Brewster, M. E., Huang, M.-J., Pop, E. and Bodor, N. (1993), Hydroxyl stretching in substituted phenols: An AM1 study. Int. J. Quantum Chem., 48: 7–15. doi: 10.1002/qua.560480705
- Issue published online: 19 OCT 2004
- Article first published online: 19 OCT 2004
- Manuscript Received: 24 JUN 1993
Hydroxyl-stretching frequencies (vOH) were estimated for a number of 4-substituted and 2,6-disubstituted phenols using the AM1 all-valence electron molecular orbital approximation. There was significant correlation between calculated and experimentally observed frequencies with better correlation observed with the gas phase as compared with dilute solution-phase values. Significant Hammett sigma–rho relationships were recorded for the 4-substituted phenols, consistent with experimental observations. The vOH stretching frequency associated with the equilibrium structure of 2,6-di-t-butylphenol was calculated to be 15 cm−1 higher than that of phenol and this increase was attributed to steric interactions that act to effectively shorten the OH bond length. © 1993 John Wiley & Sons, Inc.