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RESEARCH PRODUCT
Carbonyl Hypoiodites as Extremely Strong Halogen Bond Donors
Jas S. WardKari RissanenKhai-nghi TruongShilin Yusubject
Halogen Bondingpyridineinorganic chemicalsHalogen bondOrganic basehalogeenitCommunicationSupramolecular chemistryGeneral ChemistryNuclear magnetic resonance spectroscopyGeneral MedicinehypoioditeMedicinal chemistryCatalysisCommunicationssupramolecular chemistrychemistry.chemical_compoundkemialliset sidoksetNMR spectroscopychemistryPyridineTrifluoroacetic acidsupramolekulaarinen kemiaMoietyCarboxylatedescription
Abstract Neutral halogen‐bonded O−I−N complexes were prepared from in situ formed carbonyl hypoiodites and aromatic organic bases. The carbonyl hypoiodites have a strongly polarized iodine atom with larger σ‐holes than any known uncharged halogen bond donor. Modulating the Lewis basicity of the selected pyridine derivatives and carboxylates leads to halogen‐bonded complexes where the classical O−I⋅⋅⋅N halogen bond transforms more into a halogen‐bonded COO−⋅⋅⋅I−N+ ion‐pair (salt) with an asymmetric O−I−N moiety. X‐ray analyses, NMR studies, and calculations reveal the halogen bonding geometries of the carbonyl hypoiodite‐based O−I−N complexes, confirming that in the solid‐state the iodine atom is much closer to the N‐atom of the pyridine derivatives than its original position at the carboxylate O‐atom.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-08-24 | Angewandte Chemie |