Published February 11, 2000
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Journal Article
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A Computational Study of Nicotine Conformations in the Gas Phase and in Water
- Creators
- Elmore, Donald E.
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Dougherty, Dennis A.
Abstract
The conformational preferences of nicotine in three protonation states and in the gas phase as well as aqueous solution are investigated using several computational procedures. Conformational aspects emphasized are N-methyl stereochemistry, relative rotation of the pyridine and pyrrolidine rings, and pyrrolidine ring conformation. All methods consistently predicted that the N-methyl trans species are most stable for all protonation states in both gas phase and in water. However, the cis/trans energy gap is significantly reduced in water. Additionally, the two pyridine ring rotamers, which are energetically equivalent in the gas phase, experience different solvation energies in water.
Additional Information
© 2000 American Chemical Society. Received 1 September 1999. Published online 20 January 2000. Published in print 1 February 2000. We gratefully acknowledge Dr. Jiabo Li, Professor Christopher Cramer, and Professor Donald Truhlar of the University of Minnesota for providing the Gaussian Solvation Module and for many helpful discussions. Justin P. Gallivan (Caltech) also provided valuable assistance. D.E.E. is an NSF Predoctoral Fellow. This work was supported by NIH (NS 34407).Attached Files
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Additional details
- Eprint ID
- 76989
- DOI
- 10.1021/jo991383q
- Resolver ID
- CaltechAUTHORS:20170427-092715605
- NSF Predoctoral Fellowship
- NS 34407
- NIH
- Created
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2017-04-27Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field