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Updated: Apr 17, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Generating and trapping metalla-N-heterocyclic carbenes
Javier Ruiz1, Lucía García, Marilín Vivanco
1Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Facultad de Química, 33006 Oviedo (Spain). jruiz@uniovi.es.
Abstract:
By means of a combined experimental and theoretical approach, the electronic features and chemical behavior of metalla-N-heterocyclic carbenes (MNHCs, N-heterocyclic carbenes containing a metal atom within the heterocyclic skeleton) have been established and compared with those of classical NHCs. MNHCs are strongly basic (proton affinity and pK(a) values around 290 kcal mol(-1) and 36, respectively) with a narrow singlet-triplet gap (around 23 kcal mol(-1)). MNHCs can be generated from the corresponding metalla-imidazolium salts and trapped by addition of transition-metal complexes affording the corresponding heterodimetallic dicarbene derivatives, which can serve as carbene transfer agents.
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