Issue 32, 2021

In silico characterization and prediction of thiourea-like neutral bidentate halogen bond catalysts

Abstract

Preorganization is a common strategy to align halogen bond (XB) donors to form two or more halogen bonds simultaneously. Previous approaches have utilized various non-covalent interactions such as steric interactions, π⋯π stacking, and hydrogen bond interactions. However, some of the introduced aligning interactions may compete with halogen bond interactions if the donors are employed in catalysis. To achieve thiourea-like properties, we have designed in silico several neutral bidentate halogen bond donors in whose structures the donor moieties are connected via covalent bonds. Compared to previous XB catalyst designs, the new design does not involve other potentially competitive non-covalent interactions such as hydrogen bonds. One of the designed XB donors can deliver strong halogen bonds, with a O–I distance as short as 2.64 Å. Density functional theory (DFT) calculations predicted that our designed catalysts may catalyze important organic reactions on their own, particularly for those reactions that involve (developing) soft anions such as thiolates.

Graphical abstract: In silico characterization and prediction of thiourea-like neutral bidentate halogen bond catalysts

Supplementary files

Article information

Article type
Paper
Submitted
05 Jun 2021
Accepted
24 Jul 2021
First published
27 Jul 2021

Org. Biomol. Chem., 2021,19, 7051-7060

In silico characterization and prediction of thiourea-like neutral bidentate halogen bond catalysts

H. Yang, C. Tan and M. W. Wong, Org. Biomol. Chem., 2021, 19, 7051 DOI: 10.1039/D1OB01092A

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