The conformational preference of 2,2′-bisanilides was investigated by variable-temperature NMR spectroscopy, NMR titration and diffusion experiments, IR spectroscopy, computational analysis, and X-ray crystallography. The formation of a conformation having the two amide moieties linked by an intramolecular hydrogen bond was detected at low temperatures. The interconversion kinetics of the two conformational species of bisanilide 2 were determined by NMR line shape analysis. The formation of a supramolecule linked by intermolecular hydrogen bonds was ruled out by means of DMSO titration, DOSY experiments, and steric considerations.
Mazzanti, A., Chiarucci, M., Prati, L., Bentley, K.W., Wolf, C. (2016). Computational and DNMR Analysis of the Conformational Isomers and Stereodynamics of Secondary 2,2′-Bisanilides. JOURNAL OF ORGANIC CHEMISTRY, 81(1), 89-99 [10.1021/acs.joc.5b02330].
Computational and DNMR Analysis of the Conformational Isomers and Stereodynamics of Secondary 2,2′-Bisanilides
MAZZANTI, ANDREA;CHIARUCCI, MICHEL;PRATI, LUCA;
2016
Abstract
The conformational preference of 2,2′-bisanilides was investigated by variable-temperature NMR spectroscopy, NMR titration and diffusion experiments, IR spectroscopy, computational analysis, and X-ray crystallography. The formation of a conformation having the two amide moieties linked by an intramolecular hydrogen bond was detected at low temperatures. The interconversion kinetics of the two conformational species of bisanilide 2 were determined by NMR line shape analysis. The formation of a supramolecule linked by intermolecular hydrogen bonds was ruled out by means of DMSO titration, DOSY experiments, and steric considerations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
