Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 46, Pages 11983-11988Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101742
Keywords
carbenes; computational analysis; mesoionic; sigma donor; pi acidity; radicals; tin
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Funding
- Ecole Polytechnique Federale de Lausanne (EPFL)
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The study found that mesoionic imidazolylidenes bearing a diphenyltriazinyl (Dpt) substituent exhibit improved pi-acidic properties compared to Arduengo-type N-heterocyclic carbenes. This discovery was supported by computational analysis and experimental evidence. The new carbene was utilized to stabilize a low-valent paramagnetic tin compound, demonstrating its usefulness.
Mesoionic imidazolylidenes are recognized as excellent electron-donating ligands in organometallic and main group chemistry. However, these carbene ligands typically show poor pi-accepting properties. A computational analysis of 71 mesoionic imidazolylidenes that bear different aryl or heteroaryl substituents in C2 position was performed. The study has revealed that a diphenyltriazinyl (Dpt) substituent renders the corresponding carbene particularly pi-acidic. The computational results could be corroborated experimentally. A mesoionic imidazolylidene with a Dpt substituent was found to be a better sigma-donor and a better pi-acceptor compared to an Arduengo-type N-heterocyclic carbene. To demonstrate the utility of the new carbene, the ligand was used to stabilize a low-valent paramagnetic tin compound.
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