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

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• 作者：Andrea Mazzanti ; Michel Chiarucci ; Luca Prati ; Keith W. Bentley ; Christian Wolf
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：January 4, 2016
• 年：2016
• 卷：81
• 期：1
• 页码：89-99
• 全文大小：530K
• ISSN：1520-6904

文摘

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.