ArticleChemphyschem : a European journal of chemical physics and physical chemistry2023
A Quantum-chemical Analysis on the Lewis Acidity of Diarylhalonium Ions.
Article in Chemphyschem : a European journal of chemical physics and physical chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Probing Weak Halogen Bonding in Aqueous Solution.Journal of the American Chemical Society · 2026Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors.Beilstein journal of organic chemistry · 2024Article
- An efficient and chemoselective method to generate arynes.Chemical science · 2023Article
- Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications.Chemical reviews · 2023Review
- A Quantum-chemical Analysis on the Lewis Acidity of Diarylhalonium Ions.Chemphyschem : a European journal of chemical physics and physical chemistry · 2023Article
- Chiral Bromonium Salt (Hypervalent Bromine(III)) withMolecules (Basel, Switzerland) · 2023Article
- Synthesis and reactivity of azole-based iodazinium salts.Beilstein journal of organic chemistry · 2023Article
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Authors and funding
4 authors.
Funding
Abstract
Cyclic diaryliodonium compounds like iodolium derivatives have increasingly found use as noncovalent Lewis acids in the last years. They are more stable toward nucleophilic substitution than acyclic systems and are markedly more Lewis acidic. Herein, this higher Lewis acidity is analyzed and explained via quantum-chemical calculations and energy decomposition analyses. Its key origin is the change in energy levels and hybridization of iodine's orbitals, leading to both more favorable electrostatic interaction and better charge transfer. Both of the latter seem to contribute in similar fashion, while hydrogen bonding as well as steric repulsion with the phenyl rings play at best a minor role. In comparison to iodolium, bromolium and chlorolium are less Lewis acidic the lighter the halogen, which is predominantly based on less favorable charge-transfer interactions.
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Registered trials
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