Issue 71, 2022

A predictive journey towards trans-thioamides/amides

Abstract

The cistrans isomerization of (thio)amides was studied by DFT calculations to get the model for the higher preference for the cis conformation by guided predictive chemistry, suggesting how to select the alkyl/aryl substituents on the C/N atoms that lead to the trans isomer. Multilinear analysis, together with cross-validation analysis, helped to select the best fitting parameters to achieve the energy barriers of the cis to trans interconversion, as well as the relative stability between both isomers. Double experimental check led to the synthesis of the best trans candidate with sterically demanding t-butyl substituents, confirming the utility of predictive chemistry, bridging organic and computational chemistry.

Graphical abstract: A predictive journey towards trans-thioamides/amides

Supplementary files

Article information

Article type
Communication
Submitted
29 Jul 2022
Accepted
10 Aug 2022
First published
10 Aug 2022

Chem. Commun., 2022,58, 9950-9953

Author version available

A predictive journey towards trans-thioamides/amides

M. Tomasini, J. Zhang, H. Zhao, E. Besalú, L. Falivene, L. Caporaso, M. Szostak and A. Poater, Chem. Commun., 2022, 58, 9950 DOI: 10.1039/D2CC04228B

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