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Catalysts 2016, 6(11), 178; doi:10.3390/catal6110178

Advances in the Knowledge of N-Heterocyclic Carbenes Properties. The Backing of the Electrochemical Investigation

1
Department SBAI, Sapienza University of Rome, via Castro Laurenziano, 7, 00161 Rome, Italy
2
Via Antelao, 9, 00141 Rome, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Federico Cisnetti
Received: 25 October 2016 / Revised: 9 November 2016 / Accepted: 10 November 2016 / Published: 16 November 2016
(This article belongs to the Special Issue Tailor-Made NHC Ligands)
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Abstract

In the last twenty years, N-heterocyclic carbenes (NHCs) have acquired considerable popularity as ligands for transition metals, organocatalysts and in metal-free polymer synthesis. NHCs are generally derived from azolium based salts NHCH+X by deprotonation or reduction (chemical or electrochemical) of NHCH+. The extensive knowledge of the physicochemical properties of NHCH+/NHC system could help to select the conditions (scaffold of NHC, nature of the counter-ion X, solvent, etc.) to enhance the catalytic power of NHC in a synthesis. The electrochemical behavior of NHCH+/NHC system, in the absence and in the presence of solvent, was extensively discussed. The cathodic reduction of NHCH+ to NHC and the anodic oxidation of NHC, and the related effect of the scaffold, solvent, and electrodic material were emphasized. The electrochemical investigations allow acquiring further knowledge as regards the stability of NHC, the acidic and nucleophilic properties of NHCH+/NHC system, the reactivity of NHC versus carbon dioxide and the effect of the hydrogen bond on the catalytic efficiency of NHC. The question of the spontaneous or induced formation of NHC from particular ionic liquids was reconsidered via voltammetric analysis. The results suggested by the classical and the electrochemical methodologies were compared and discussed. View Full-Text
Keywords: N-heterocyclic carbene (NHC); cyclic voltammetry; electrolysis; NHC stability; NHC nucleophilicity; azolium acidity; electrogenerated NHC; hydrogen bond; carbon dioxide; NHC–CO2 adduct N-heterocyclic carbene (NHC); cyclic voltammetry; electrolysis; NHC stability; NHC nucleophilicity; azolium acidity; electrogenerated NHC; hydrogen bond; carbon dioxide; NHC–CO2 adduct
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Feroci, M.; Chiarotto, I.; Inesi, A. Advances in the Knowledge of N-Heterocyclic Carbenes Properties. The Backing of the Electrochemical Investigation. Catalysts 2016, 6, 178.

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