ArticleChemistryOpen2020
Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution.
Article in ChemistryOpen, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Redox activation of halogen-bonding catalysts for organic synthesis.Chemical science · 2026Article
- Highly Enantioselective Organocatalysis with Bidentate Halogen Bond Donors.Angewandte Chemie (International ed. in English) · 2025Article
- Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications.Chemical reviews · 2023Review
- Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds.Chemical communications (Cambridge, England) · 2022Article
- N-Heterocyclic Iod(az)olium Salts - Potent Halogen-Bond Donors in Organocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- A Bidentate Iodine(III)-Based Halogen-Bond Donor as a Powerful Organocatalyst*.Angewandte Chemie (International ed. in English) · 2021Article
- Activation of a Metal-Halogen Bond by Halogen Bonding.Angewandte Chemie (International ed. in English) · 2020Article
- Bidentate Chiral Bis(imidazolium)-Based Halogen-Bond Donors: Synthesis and Applications in Enantioselective Recognition and Catalysis.Angewandte Chemie (International ed. in English) · 2020Article
- Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution.ChemistryOpen · 2020Article
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3 authors.
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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.
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