title: A computational study of nicotine conformations in the gas phase and in water.
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.
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: D E
authors.initials: DE
authors.lastname: Elmore
authors.forename: D A
authors.initials: DA
authors.lastname: Dougherty
mesh_terms: D005740:Gases / Q000737:chemistry; D008968:Molecular Conformation; D009538:Nicotine / Q000737:chemistry*; D012995:Solubility; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
chemical_list: D005740:Gases; D014867:Water; D009538:Nicotine