1,3-dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct.
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 pi-stacked rings and two-dimensional sheets constructed by hydrogen-bonds from imidazolium-ring hydrogens to the carboxylate group.
Holbrey
John D
JD
Center for Green Manufacturing, Department of Chemistry, University of Alabama, Tuscaloosa, AL 35487, USA.
Reichert
W Matthew
WM
Tkatchenko
Igor
I
Bouajila
Ezzedine
E
Walter
Olaf
O
Tommasi
Immacolata
I
Rogers
Robin D
RD