A Computational Study of Nicotine Conformations in the Gas Phase and in Water
2000; American Chemical Society; Volume: 65; Issue: 3 Linguagem: Inglês
10.1021/jo991383q
ISSN1520-6904
AutoresDonald E. Elmore, Dennis A. Dougherty,
Tópico(s)Protein Structure and Dynamics
ResumoThe 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.
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