Stable Mesoionic N‐Heterocyclic Olefins (mNHOs)
Abstract: We report a new class of stable mesoionic N‐heterocyclic olefins, featuring a highly polarized (strongly ylidic) double bond. The ground‐state structure cannot be described through an uncharged mesomeric Lewis‐structure, thereby structurally distinguishing them from traditional N‐heterocyclic olefins (NHOs). mNHOs can easily be obtained through deprotonation of the corresponding methylated N,N′‐diaryl‐1,2,3‐triazolium and N,N′‐diaryl‐imidazolium salts, respectively. In their reactivity, they represent strong σ‐donor ligands as shown by their coordination complexes of rhodium and boron. Their calculated proton affinities, their experimentally derived basicities (competition experiments), as well as donor abilities (Tolman electronic parameter; TEP) exceed the so far reported class of NHOs.
- 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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Stable Mesoionic N‐Heterocyclic Olefins (mNHOs) ; volume:59 ; number:14 ; year:2020 ; pages:5782-5787 ; extent:6
Angewandte Chemie / International edition. International edition ; 59, Heft 14 (2020), 5782-5787 (gesamt 6)
- Creator
- DOI
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10.1002/anie.201914571
- URN
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urn:nbn:de:101:1-2022061211173294299355
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:25 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Hansmann, Max M.
- Antoni, Patrick W.
- Pesch, Henner
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Sydnone Methides: Intermediates between Mesoionic Compounds and Mesoionic N‐Heterocyclic Olefins
N‐Heterocyclic Olefins on a Metallic Surface – Adsorption, Orientation, and Electronic Influence
Pushing the upper limit of nucleophilicity scales by mesoionic N‐heterocyclic olefins
N-Heterocyclic carbenes
Stable Mesoionic N‐Heterocyclic Olefins (mNHOs)
N‐Heterocyclic Olefins on a Silicon Surface
N-Heterocyclic Olefins with Applications to ROP
N‐Heterocyclic Olefins on a Silicon Surface
N‐Heterocyclic Olefins on a Silicon Surface
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Self‐Assembled Monolayers of N‐Heterocyclic Olefins on Au (111)
Self‐Assembled Monolayers of N‐Heterocyclic Olefins on Au (111)
Sydnone Methides: Intermediates between Mesoionic Compounds and Mesoionic N‐Heterocyclic Olefins
N‐Heterocyclic Olefins on a Metallic Surface – Adsorption, Orientation, and Electronic Influence
Pushing the upper limit of nucleophilicity scales by mesoionic N‐heterocyclic olefins