13724-10-2Relevant academic research and scientific papers
Solvent effects on barrier to rotation of enaminonitriles using inversion transfer (1)H NMR spectroscopy and FTIR spectroscopy.
Kaur, Sarjit,Eberhardt, Eric S,Doucette, Amanda,Chase, Adrien,Dalby, Charlie
, p. 3937 - 3940 (2002)
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.
The analogy between C=O and C(CN)2. Part 2.1 Structural properties of N,N-dialkylaminobenzamides and the analogously substituted 2-(phenylmethylene)propanedinitriles
Karlsen, Hege,Kolsaker, Per,Romming, Christian,Uggerud, Einar
, p. 404 - 409 (2007/10/03)
The barrier to rotation around the carbon amino nitrogen bond in 2-[N,N-dimethylamino(phenyl)methylene]-propanedinitrile (4a), 2-[N,N-diethylamino(phenyl)methylene]propanedinitrile (4b), 2-[(phenyl)pyrrolidin-1-ylmethylene]propanedinitrile (4c), N,N-dimethylbenzamide (5a), N,N-diethylbenzamide (5b) and (phenyl)pyrrolidin-1-ylmethanone (5c) were determined using dynamic 1H NMR spectroscopy. X-Ray crystal structures of 4a, 4b, 4c and 5a were determined, and quantum chemical calculations were carried out for 4a and 5a and for the transition structures for the rotation process of these two compounds. The barriers were generally lower than for the vinyl analogues 1 and 2. Although the calculated transition structures for 4a and 5a indicate some steric strain, the reduction of the barriers, especially for series 4, indicates that steric strain is more important in the ground state, thus raising its energy relatively more than for the transition state.
Orthoamides, LVIII. Condensation reactions of CH2-acidic compounds with orthoamides of carboxylic acids and alkyne carboxylic acids
Kantlehner, Willi,Haug, Erwin,Stieglitz, Rüdiger,Frey, Wolfgang,Kress, Ralf,Mezger, Jochen
, p. 399 - 419 (2007/10/03)
The orthoamide derivatives 1s and 2e were prepared from the guanidinium salt 7a and the appropriate carbanions. Cleavage of the orthoamide 2e with benzoyl chloride affords the amidinium salt 10a, which can be transformed into the amidinium salt 10b by an
