Gauging Radical Stabilization with Carbenes
Abstract: Carbenes, including N‐heterocyclic carbene (NHC) ligands, are used extensively to stabilize open‐shell transition metal complexes and organic radicals. Yet, it remains unknown, which carbene stabilizes a radical well and, thus, how to design radical‐stabilizing C‐donor ligands. With the large variety of C‐donor ligands experimentally investigated and their electronic properties established, we report herein their radical‐stabilizing effect. We show that radical stabilization can be understood by a captodative frontier orbital description involving π‐donation to‐ and π‐donation from the carbenes. This picture sheds a new perspective on NHC chemistry, where π‐donor effects usually are assumed to be negligible. Further, it allows for the intuitive prediction of the thermodynamic stability of covalent radicals of main group‐ and transition metal carbene complexes, and the quantification of redox non‐innocence.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Gauging Radical Stabilization with Carbenes ; day:04 ; month:08 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (04.08.2022) (gesamt 1)
- DOI
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10.1002/anie.202206390
- URN
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urn:nbn:de:101:1-2022080515065302575183
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:28 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
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Dirac sigma models from gauging
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An Air‐Stable, Neutral Phenothiazinyl Radical with Substantial Radical Stabilization Energy
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En-gauging naturalness
Reactivity of carbenes with Lewis acids
N-Heterocyclic carbenes
Gauging triple stores with actual biological data
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