Issue 1, 2003
From the journal:

Chemical Communications

1,3-Dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct†

John D. Holbrey,a   W. Matthew Reichert,a   Igor Tkatchenko,*b   Ezzedine Bouajila,b   Olaf Walter,c   Immacolata Tommasid  and  Robin D. Rogers*a  

* Corresponding authors

a Center for Green Manufacturing and Department of Chemistry, The University of Alabama, Tuscaloosa, AL, USA
E-mail: rdrogers@bama.ua.edu
Fax: 205 348 0823
Tel: 205 348 4323

b Laboratoire de Synthèse et Electrosynthèse Organométallique, UMR 5632 CNRS-Université de Bourgogne, Faculté des Sciences Mirande, 9 ave A. Savary, BP 47870, Dijon Cedex, France
E-mail: tkatchen@u-bourgogne.fr

c Institut für Technische Chemie-CPV, Forschungszentrum Karlsruhe, PO Box 3640, Karlsruhe, Germany

d Department of Chemistry, University of Bari, Campus Universitario, Bari, Italy

Abstract

1,3-Dimethylimidazolium-2-carboxylate is formed in good yield, rather than the anticipated organic salt, 1,3-dimethylimidazolium methyl carbonate, as the reaction product resulting from both N-alkylation and C-carboxylation of 1-methylimidazole with dimethyl carbonate; the crystal structure of the zwitterion exhibits π-stacked rings and two-dimensional sheets constructed by hydrogen-bonds from imidazolium-ring hydrogens to the carboxylate group.

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Article information

DOI
https://doi.org/10.1039/B211519K
Article type
Communication
Submitted
27 Sep 2002
Accepted
15 Nov 2002
First published
05 Dec 2002

Chem. Commun., 2003, 28-29

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1,3-Dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct

J. D. Holbrey, W. M. Reichert, I. Tkatchenko, E. Bouajila, O. Walter, I. Tommasi and R. D. Rogers, Chem. Commun., 2003, 28 DOI: 10.1039/B211519K

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