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A Computational Study of Nicotine Conformations in the Gas Phase and in Water

Elmore, Donald E. and Dougherty, Dennis A. (2000) A Computational Study of Nicotine Conformations in the Gas Phase and in Water. Journal of Organic Chemistry, 65 (3). pp. 742-747. ISSN 0022-3263. doi:10.1021/jo991383q.

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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.

Item Type:Article
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Dougherty, Dennis A.0000-0003-1464-2461
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).
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NSF Predoctoral FellowshipUNSPECIFIED
NIHNS 34407
Issue or Number:3
Record Number:CaltechAUTHORS:20170427-092715605
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Official Citation:A Computational Study of Nicotine Conformations in the Gas Phase and in Water Donald E. Elmore and Dennis A. Dougherty The Journal of Organic Chemistry 2000 65 (3), 742-747 DOI: 10.1021/jo991383q
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76989
Deposited By: Ruth Sustaita
Deposited On:27 Apr 2017 16:45
Last Modified:15 Nov 2021 17:04

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