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

Francesca D'Anna, Carla Rizzo, Isabella Chiarotto, Marta Feroci, Achille Inesi, Luigi Ornano

Risultato della ricerca: Article

3 Citazioni (Scopus)

Abstract

In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azolium and acetate solutions, the proton exchange equilibrium between azolium cations 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 Elsevier B.V. All rights reserved.
Lingua originaleEnglish
pagine (da-a)55-58
Numero di pagine4
RivistaElectrochemistry Communications
Volume67
Stato di pubblicazionePublished - 2016

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Benzoin
Cations
Acetates
Salts
Positive ions
Ions
Deprotonation
Acidity
Cyclic voltammetry
Protons
Condensation
Ion exchange
carbene
tetrabutylammonium

All Science Journal Classification (ASJC) codes

  • Electrochemistry

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Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis. / D'Anna, Francesca; Rizzo, Carla; Chiarotto, Isabella; Feroci, Marta; Inesi, Achille; Ornano, Luigi.

In: Electrochemistry Communications, Vol. 67, 2016, pag. 55-58.

Risultato della ricerca: Article

D'Anna, Francesca ; Rizzo, Carla ; Chiarotto, Isabella ; Feroci, Marta ; Inesi, Achille ; Ornano, Luigi. / Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis. In: Electrochemistry Communications. 2016 ; Vol. 67. pagg. 55-58.
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abstract = "In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azolium and acetate solutions, the proton exchange equilibrium between azolium cations 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. {\circledC} 2016 Elsevier B.V. All rights reserved.",
author = "Francesca D'Anna and Carla Rizzo and Isabella Chiarotto and Marta Feroci and Achille Inesi and Luigi Ornano",
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T1 - Azolium and acetate ions in DMF: Formation of free N-heterocyclic carbene. A voltammetric analysis

AU - D'Anna, Francesca

AU - Rizzo, Carla

AU - Chiarotto, Isabella

AU - Feroci, Marta

AU - Inesi, Achille

AU - Ornano, Luigi

PY - 2016

Y1 - 2016

N2 - In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azolium and acetate solutions, the proton exchange equilibrium between azolium cations 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 Elsevier B.V. All rights reserved.

AB - In order to reveal the possible formation of free N-heterocyclic carbene (NHC) in DMF-azolium and acetate solutions, the proton exchange equilibrium between azolium cations 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 Elsevier B.V. All rights reserved.

UR - http://hdl.handle.net/10447/177662

M3 - Article

VL - 67

SP - 55

EP - 58

JO - Electrochemistry Communications

JF - Electrochemistry Communications

SN - 1388-2481

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