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Volumn 65, Issue 3, 2000, Pages 742-747

A computational study of nicotine conformations in the gas phase and in water

Author keywords

[No Author keywords available]

Indexed keywords

NICOTINE; PYRIDINE; PYRROLIDINE DERIVATIVE; WATER;

EID: 0033975523     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991383q     Document Type: Article
Times cited : (69)

References (40)
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  • 2
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    • For introductions to nicotine pharmacology and the interest in nicotinic agonists and antagonists, see: Bannon, A. W., et al. Science 1998, 279, 77-81. Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1997, 40, 4169-4194. Elgen, R. M.; Hunter, J. C.; Dray, A. Trends Pharm. Sci. 1999, 20, 337-342.
    • (1997) J. Med. Chem. , vol.40 , pp. 4169-4194
    • Holladay, M.W.1    Dart, M.J.2    Lynch, J.K.3
  • 3
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    • For introductions to nicotine pharmacology and the interest in nicotinic agonists and antagonists, see: Bannon, A. W., et al. Science 1998, 279, 77-81. Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1997, 40, 4169-4194. Elgen, R. M.; Hunter, J. C.; Dray, A. Trends Pharm. Sci. 1999, 20, 337-342.
    • (1999) Trends Pharm. Sci. , vol.20 , pp. 337-342
    • Elgen, R.M.1    Hunter, J.C.2    Dray, A.3
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    • (b) Koo, C. H.; Kim, H. S. Daehan Hwahak Hwoejee 1965, 9, 134-141. Koo, C. H.; Kim, H. S. Chem. Abstr. 1966, 64, 6431e.
    • (1965) Daehan Hwahak Hwoejee , vol.9 , pp. 134-141
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  • 6
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    • (b) Koo, C. H.; Kim, H. S. Daehan Hwahak Hwoejee 1965, 9, 134-141. Koo, C. H.; Kim, H. S. Chem. Abstr. 1966, 64, 6431e.
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    • Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612
    • SPARTAN version 5.0. Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
    • SPARTAN Version 5.0
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    • Department of Chemistry, Yale University, P.O. Box 208107, New Haven, CT 06520-8107
    • BOSS Version 3.8. Jorgensen, W. L. Department of Chemistry, Yale University, P.O. Box 208107, New Haven, CT 06520-8107.
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    • note
    • sol of the other nicotine protonation states (neutral and doubly protonated) was performed using the SM5.42R HF/6-31G* parametrized model on HF/6-31G** geometries. This model was applied to these systems in lieu of SPT/OPLS simulations because it produced similar qualitative trends for the singly protonated species at a fraction of the computational expense. The same cis/trans solvation trend seen for + species was seen for other protonation states, and trans species are still predicted to be most stable in aqueous solution. But interestingly, the B rotamers for both 0 and ++ species showed better solvation than the A ones. Thus, in species where the N atoms carry a similar charge, solvation appears to improve with decreased N-N distance.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.