title: Computational and DNMR Analysis of the Conformational Isomers and Stereodynamics of Secondary 2,2'-Bisanilides.
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.
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", University of Bologna , Viale Risorgimento 4, I-40136 Bologna, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", University of Bologna , Viale Risorgimento 4, I-40136 Bologna, Italy.
authors.forename: Michel
authors.initials: M
authors.lastname: Chiarucci
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", University of Bologna , Viale Risorgimento 4, I-40136 Bologna, Italy.
authors.forename: Luca
authors.initials: L
authors.lastname: Prati
authors.affiliation: Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
authors.forename: Keith W
authors.initials: KW
authors.lastname: Bentley
authors.affiliation: Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
authors.forename: Christian
authors.initials: C
authors.lastname: Wolf