Influence of Intramolecular Hydrogen Bonding on the Nitrogen Lone Electron Pair of Oxymorphone

Authors

Steve Scheiner, Utah State UniversityFollow
Vera M. Kolb, Southern Illinois University Carbondale

Document Type

Article

Journal/Book Title

Proceedings of the National Academy of Sciences

Publication Date

10-1980

Publisher

National Academy of Sciences

Volume

77

Issue

10

First Page

5602

Last Page

5605

Abstract

Approximate ab initio molecular orbital methods are used to examine the structural and electronic properties of oxymorphone. The most stable conformation of the molecule is found to include an intramolecular hydrogen bond between the C-14 hydroxyl group and the nitrogen atom in agreement with available experimental data. The total molecular electron density is transformed to a set of localized molecular orbitals, one of which corresponds to the lone electron pair on nitrogen. The hydrogen bond is shown to produce substantial bending and stretching of the lone pair when compared to its shape when such hydrogen bonding is precluded.

Comments

http://www.pnas.org/content/77/10/5602.short

Publisher PDF is available for download through the link above.

Published by National Academy of Sciences in Proceedings of the National Academy of Sciences.

Recommended Citation

Influence of Intramolecular Hydrogen Bonding on the Nitrogen Lone Electron Pair of Oxymorphone S. Scheiner and V. M. Kolb Int. J. Quantum Chem. Quantum Biology Symp. No. 7, 433 (1980)