Computational and DNMR Analysis of the Conformational Isomers and Stereodynamics of Secondary 2,2'-Bisanilides

Andrea Mazzanti; Michel Chiarucci; Luca Prati; Keith W Bentley; Christian Wolf

doi:10.1021/acs.joc.5b02330

Computational and DNMR Analysis of the Conformational Isomers and Stereodynamics of Secondary 2,2'-Bisanilides

J Org Chem. 2016 Jan 4;81(1):89-99. doi: 10.1021/acs.joc.5b02330. Epub 2015 Dec 18.

Authors

Andrea Mazzanti¹, Michel Chiarucci¹, Luca Prati¹, Keith W Bentley², Christian Wolf²

Affiliations

¹ Department of Industrial Chemistry "Toso Montanari", University of Bologna , Viale Risorgimento 4, I-40136 Bologna, Italy.
² Department of Chemistry, Georgetown University , Washington, DC 20057, United States.

PMID: 26656940
DOI: 10.1021/acs.joc.5b02330

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.