Synthesis and properties of a group of chiral ionic liquids with chiral anions

ANYL 70

Shaofang Yu, Shaofang.Yu@Marquette.edu and Chieu D. Tran. Department of Chemistry, Marquette University, 535 N 14th St., Milwaukee, WI 53233
A group of ionic liquids composed of either chiral anions and nonchiral cations or both chiral anions and chiral cations were synthesized in a simple one-pot reaction. The chiral anions are various chelated orthoborates and the cations are either 1-butyl-3-methylimidazolium or 1-ethyl-3-methylimidazolium or 1-methyl-3-[(2S)-2-methylbutyl]-imidazolium. 11 pairs of these ionic liquids are liquid at room temperature and 4 of them are solid. These ionic liquids stable up to 250 ºC and their glass transition temperature ranges from –70.4 °C to -0.53ºC. Crystals of two of the solid ionic liquids were obtained and studied with X-Ray crystallography and indicates that the domination forces for the crystal packing are C-H•••O hydrogen bonds between the chiral anions and cations. NMR study shows that the chiral anions have good chiral selectivity ability on racemic cations of 1-methyl-3-(2-methylbutyl)-imidazolium and different selectivity abilities were observed for different anions in different solvents.
 

General Papers
7:00 PM-9:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Analytical Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006