A computational study of nicotine conformations in the gas phase and in water |
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Authors: | Elmore D E Dougherty D A |
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Affiliation: | Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA. |
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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. |
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