Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution

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ID: 106082
2020
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Abstract
Abstract Preorganization is a powerful tool in supramolecular chemistry which has been utilized successfully in intra‐ and intermolecular halogen bonding. In previous work, we had developed a bidentate bis(iodobenzimidazolium)‐based halogen bond donor which featured a central trifluoromethyl substituent. This compound showed a markedly increased catalytic activity compared to unsubstituted bis(iodoimidazolium)‐based Lewis acids, which could be explained either by electronic effects (the electron withdrawal by the fluorinated substituent) or by preorganization (the hindered rotation of the halogen bonding moieties). Herein, we systematically investigate the origin of this increased Lewis acidity via a comparison of the two types of compounds and their respective derivatives with or without the central trifluoromethyl group. Calorimetric measurements of halide complexations indicated that preorganization is the main reason for the higher halogen bonding strength. The performance of the catalysts in a series of benchmark reactions corroborates this finding.
Reference Key
voelkel2020preorganizationchemistryopen Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Voelkel, Martin H. H.;Wonner, Patrick;Huber, Prof. Dr. Stefan Matthias;
Journal chemistryopen
Year 2020
DOI
DOI not found
URL
https://doi.org/10.1002/open.201900355
Keywords
chemistry

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