title: Solvent effects on barrier to rotation of enaminonitriles using inversion transfer (1)H NMR spectroscopy and FTIR spectroscopy.
abstract: The barrier to rotation and hydrogen bonding interactions of 2,2-dicyano-1-(N,N'-dimethylamino)vinylbenzene (1) were studied in a range of solvents. The barrier to rotation of 1 in chloroform was 14.8 kcal/mol and increased by 1.7 kcal/mol in a protic solvent, trifluoroethanol. FTIR studies showed a shift in the cyano stretch of 1 to a higher wavenumber in trifluoroethanol, which is consistent with 1 participating in a hydrogen bonding interaction at the vinyl carbon (C(v)) of the enaminonitrile group.
authors.affiliation: Department of Chemistry, Vassar College, Poughkeepsie, NY 12604-0287, USA.
authors.forename: Sarjit
authors.initials: S
authors.lastname: Kaur
authors.forename: Eric S
authors.initials: ES
authors.lastname: Eberhardt
authors.forename: Amanda
authors.initials: A
authors.lastname: Doucette
authors.forename: Adrien
authors.initials: A
authors.lastname: Chase
authors.forename: Charlie
authors.initials: C
authors.lastname: Dalby
mesh_terms: D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002725:Chloroform / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics
chemical_list: D000577:Amides; D000588:Amines; D009570:Nitriles; D012997:Solvents; D002725:Chloroform