Preference of cis-Thioamide Structure in N-Thioacyl-N-methylanilines
Jin Zhang1, Zhulin Liu1, Zheng Yin1
1College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an 710021, China.
Abstract:
The thioamide group represents a highly attractive isostere of the amide bond. We report a combined structural and computational study on cis-thioamide conformation of N-thioacyl-N-methylanilines. Amide to thioamide replacement in a class of anilides that are highly valuable as conformational locks results in a higher preference for cis conformation in a unique compacted template intrinsic to the thioamide structure. The study strongly supports the use of N-methylthioanilides as cis-conformational locks in various facets of chemistry.
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