Solvent effects on barrier to rotation of enaminonitriles using inversion transfer (1)H NMR spectroscopy and FTIR spectroscopy.
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.
Kaur
Sarjit
S
Department of Chemistry, Vassar College, Poughkeepsie, NY 12604-0287, USA.
Eberhardt
Eric S
ES
Doucette
Amanda
A
Chase
Adrien
A
Dalby
Charlie
C
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
D000577:Amides; D000588:Amines; D009570:Nitriles; D012997:Solvents; D002725:Chloroform