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

被引:241
作者
Holbrey, JD
Reichert, WM
Tkatchenko, I
Bouajila, E
Walter, O
Tommasi, I
Rogers, RD
机构
[1] Univ Bourgogne, CNRS, Lab Synth & Electrosynth Organomet, UMR 5632,Fac Sci Mirande, F-21078 Dijon, France
[2] Univ Alabama, Ctr Green Mfg, Tuscaloosa, AL 35487 USA
[3] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
[4] Forschungszentrum Karlsruhe, Inst Tech Chem CPV, D-76021 Karlsruhe, Germany
[5] Univ Bari, Dept Chem, I-70126 Bari, Italy
关键词
D O I
10.1039/b211519k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:28 / 29
页数:2
相关论文
共 24 条
[1]  
ABDULSADA AK, 1986, J CHEM SOC CHEM COMM, P1253
[2]   SOLVENT-FREE SYNTHESIS OF TETRAMETHYLAMMONIUM SALTS - SYNTHESIS AND CHARACTERIZATION OF [N(CH3)(4)](2)[C2O4], [N(CH3)(4)][CO3CH4], [N(CH3)(4)][NO2], [N(CH3)(4)][CO2H], AND [N(CH3)(4)][O2C(CH2)(2)CO2CH3] [J].
ALBERT, B ;
JANSEN, M .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1995, 621 (10) :1735-1740
[3]  
BAKHTIAR C, 1994, J CHEM SOC P1, P234
[4]   STRUCTURE OF 1,3-DIMETHYLIMIDAZOLIUM-2-DITHIOCARBOXYLATE [J].
BORER, LL ;
KONG, JV ;
ORAM, DE .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :1169-1170
[5]  
BOUAJILA E, UNPUB ANGEW CHEM INT
[6]   HYDROGEN-BONDING IN IMIDAZOLIUM SALTS AND ITS IMPLICATIONS FOR AMBIENT-TEMPERATURE HALOGENOALUMINATE(III) IONIC LIQUIDS [J].
ELAIWI, A ;
HITCHCOCK, PB ;
SEDDON, KR ;
SRINIVASAN, N ;
TAN, YM ;
WELTON, T ;
ZORA, JA .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (21) :3467-3472
[7]  
Fischer J., 2001, US Pat, Patent No. [OO6175019B1, 6175019]
[8]   STRUCTURE OF 1-ETHYL-3-METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE - MODEL FOR ROOM-TEMPERATURE MOLTEN-SALTS [J].
FULLER, J ;
CARLIN, RT ;
DELONG, HC ;
HAWORTH, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :299-300
[9]   Weak intermolecular interactions in sulfonamide salts: Structure of 1-ethyl-2-methyl-3 benzyl imidazolium bis[(trifluoromethyl)sulfonyl]amide [J].
Golding, JJ ;
Macfarlane, DR ;
Spiccia, L ;
Forsyth, M ;
Skelton, BW ;
White, AH .
CHEMICAL COMMUNICATIONS, 1998, (15) :1593-1594
[10]   Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction [J].
Huddleston, JG ;
Willauer, HD ;
Swatloski, RP ;
Visser, AE ;
Rogers, RD .
CHEMICAL COMMUNICATIONS, 1998, (16) :1765-1766