In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azoliumand acetate solutions, the proton exchange equilibriumbetween azoliumcations and CH3COO−was investigated (by cyclic voltammetry) by adding CH3COOH or tetrabutylammonium acetate to DMF solutions of imidazolium or thiazolium salts of different acidity. The voltammetric analysis confirms that the deprotonation of the azolium cation by CH3COO− (with the formation of free NHC) is significant in the case of the more acidic thiazolium cations, while it is not effective with the less acidic imidazolium ones. Accordingly, the NHC-catalyzed benzoin condensation was carried out in DMF solutions of azolium salts, tetrabutylammonium acetate, and benzaldehyde. Benzoin was isolated only starting from the more acidic thiazolium salts.

Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis / Feroci, Marta; Chiarotto, Isabella; D'Anna, Francesca; Ornano, Luigi; Rizzo, Carla; Inesi, Achille. - In: ELECTROCHEMISTRY COMMUNICATIONS. - ISSN 1388-2481. - STAMPA. - 67:(2016), pp. 55-58. [10.1016/j.elecom.2016.03.012]

Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis

FEROCI, Marta;CHIAROTTO, Isabella;ORNANO, LUIGI;INESI, ACHILLE
2016

Abstract

In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azoliumand acetate solutions, the proton exchange equilibriumbetween azoliumcations and CH3COO−was investigated (by cyclic voltammetry) by adding CH3COOH or tetrabutylammonium acetate to DMF solutions of imidazolium or thiazolium salts of different acidity. The voltammetric analysis confirms that the deprotonation of the azolium cation by CH3COO− (with the formation of free NHC) is significant in the case of the more acidic thiazolium cations, while it is not effective with the less acidic imidazolium ones. Accordingly, the NHC-catalyzed benzoin condensation was carried out in DMF solutions of azolium salts, tetrabutylammonium acetate, and benzaldehyde. Benzoin was isolated only starting from the more acidic thiazolium salts.
2016
Acetic acid; Azolium salts; Benzoin condensation; Cyclic voltammetry; NHC; Tetrabutylammonium acetate; Electrochemistry
01 Pubblicazione su rivista::01a Articolo in rivista
Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis / Feroci, Marta; Chiarotto, Isabella; D'Anna, Francesca; Ornano, Luigi; Rizzo, Carla; Inesi, Achille. - In: ELECTROCHEMISTRY COMMUNICATIONS. - ISSN 1388-2481. - STAMPA. - 67:(2016), pp. 55-58. [10.1016/j.elecom.2016.03.012]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/867532
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