The Core Difference between a Mesoionic and a Normal N-Heterocyclic Carbene
ACS Omega2022Vol. 7(38), pp. 34657–34664
Citations Over TimeTop 20% of 2022 papers
Abstract
The properties of the abnormal N-heterocyclic carbene (NHC) 1,4-dimesityl-3-methyl-1,2,3-triazolin-5-ylidene were comprehensively compared to those of the related normal carbene 1,3-dimesitylimidazolin-2-ylidene using a range of steric and electronic probe techniques (% V bur, steric maps, Tolman electronic parameter, alane, Huynh electronic parameter, selone, and pK a values). The two NHCs were determined to be sterically equivalent (isostructural), while the triazolin-5-ylidene was found to be a stronger σ-electron donor and a much weaker π-electron acceptor. These results were used to demonstrate that the electronic properties of these NHCs could affect the stereochemical outcome of an NHC-catalyzed reaction.
Related Papers
- → Palladium‐Catalyzed Direct C2‐Arylation of an N‐Heterocyclic Carbene: An Atom‐Economic Route to Mesoionic Carbene Ligands(2015)73 cited
- → Gold(III)‐ versus Gold(I)‐Induced Cyclization: Synthesis of Six‐Membered Mesoionic Carbene and Acyclic (Aryl)(Heteroaryl) Carbene Complexes(2012)59 cited
- → Normal and Abnormal N-Heterocyclic Carbene Ligands(2014)51 cited
- → Iridium, ruthenium, and palladium complexes containing a mesoionic fused imidazolylidene ligand(2014)14 cited
- → ChemInform Abstract: Palladium‐Catalyzed Direct C2‐Arylation of an N‐Heterocyclic Carbene: An Atom‐Economic Route to Mesoionic Carbene Ligands.(2015)