Issue 12, 2010
From the journal:

New Journal of Chemistry

Carbenes in ionic liquids†

Oldamur Hollóczki,ab   Dirk Gerhard,c   Klemens Massone,*c   László Szarvas,c   Balázs Németh,a   Tamás Veszprémi*ab  and  László Nyulászi*ab  

* Corresponding authors

a Department of Inorganic and Analytical Chemistry, Budapest Univerity of Technology and Economics, Szt. Gellért tér 4., Budapest, Hungary
E-mail: nyulaszi@mail.bme.hu, veszpremi@mail.bme.hu
Fax: +36-1-463-3642
Tel: +36-1-463-3281

b Materials Structure and Modeling Research Group of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Szt. Gellért tér 4., Budapest, Hungary

c BASF AG, D-67056 Ludwigshafen, Germany
E-mail: klemens.massonne@basf.com

Abstract

The chemistry of 1,3-dialkylimidazolium-based ionic liquids (ILs) can easily be linked to that of N-heterocyclic carbenes (NHCs) in the presence of sufficiently basic counteranions. B3LYP/6-31+G*, B3LYP/aug-cc-pVTZ and MP2/6-311+G** studies show that increasing the basicity of the anionic component the relative stability of the ion pair and that of the hydrogen bonded complex of the corresponding free acid and NHC itself can be shifted toward the formation of NHC. In the case of the acetate anion, the ion pair and the NHC-acetic acid complex have similar stability. Photoelectron spectroscopic studies show that the vapor of EMIM-acetate is dominated by the NHC-acetic acid complex. The mass spectrum of the same compound shows the presence of both acetic acid and 1-ethyl-3-methylimidazolium-2-ylidene, in agreement with the low pressure during the MS experiment, which facilitates dissociation. The possibility of systematic and simple variation of the NHC content of the ILs facilitates the extension of carbene chemistry in ionic liquids.

Graphical abstract: Carbenes in ionic liquids

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Article information

DOI
https://doi.org/10.1039/C0NJ00380H
Article type
Paper
Submitted
19 May 2010
Accepted
18 Aug 2010
First published
05 Oct 2010

New J. Chem., 2010,34, 3004-3009

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Carbenes in ionic liquids

O. Hollóczki, D. Gerhard, K. Massone, L. Szarvas, B. Németh, T. Veszprémi and L. Nyulászi, New J. Chem., 2010, 34, 3004 DOI: 10.1039/C0NJ00380H

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