Enantioselectivity of new chiral stationary phases based on pyridinium and imidazolium ionic liquids
Abstract
The search for new systems for the analysis of chiral compounds is of interest in connection with the
development of methods for stereoselective organic synthesis and increase requirements for optical purity of
pharmaceuticals. For the analysis of volatile chiral compounds (or substances, which can be converted to
gaseous state) the most effective method is gas chromatography (GC) on columns with chiral stationary liquid
phases (SLP). Currently the main part of the GC analysis of enantiomers is performed on columns with
SLP based on cyclodextrins. The aim of the work is obtaining and studying the selectivity of a number of
new chiral phases based on imidazolium and pyridinium ionic liquids (ILs). Two possible ways of making
chiral columns based on pyridinium and imidazolium ionic liquids were investigated. The first involves the
use of a mixture of non-chiral IL as a matrix, and a chiral additive, which is a modified cyclodextrin. Another
approach involves the use of a chiral IL with chiral anon (L-tartrate and L-alanine) as the individual SLP.
In the paper studied possible ways of making columns with enantioselective SLP using pyridinium
and imidazolium ionic liquids. First used ILs with chiral anion and it is shown that the use of this kind of
chiral IL allows one to obtain the coefficients of enantioselectivity the same order as for ciclodextrin SLP.
Currently, no established methods of obtaining high-efficiency columns based on the IL. However, in the
development of successful methods of coating capillary columns with a SLP based on ILs can be a new sepa-ration instrument which can be solve the analytical problems, which to date has not been resolved since their
properties are different from the cyclodextrin columns
Downloads
References
2. Schurig V., J. Chromatogr. A, 1994, Vol. 666, pp. 111-129. Doi: 10.1016/0021-9673(94)80374-9
3. HP-Chirasyl-Val, application note., Agilent tech. 2010.
4. Kenig W.A. Gas Chromatographic enantiomer separation with modified cyclodextrins. Heidelberg, Huthig, 1992, 132 p.
5. Shashkov M.V., Sidelnikov V.N., Anal. Bioanal. Chem., 2012, Vol. 403, No 9, pp.2673-2681. doi:10.1007/s00216-012-6020-9
6. Wasserscheid P., Welton, T. Ionic liquids in synthesis. Weincheim, Germany, Wiley-VCH Verlag Gmbh&Co. KGaA, 2002, 355 p.
7. Shamsi S.A., Danielson N.D., J. Sep. Sci., 2007, Vol. 30, No 11, pp. 1729-1750. DOI: 10.1002/jssc.200700136
8. Ding J., Welton T., Armstrong D. W., Anal. Chem., 2004, Vol. 76, No 22, pp. 6819-6822. DOI: 10.1021/ac049144c
9. Berthod A., He L., Armstrong D. W., Chromatographia, 2001, Vol. 53, No 1-2, pp. 63-68. doi:10.1007/BF02492429
10.Tran C.D., Oliveira D., Yu S.F., Anal. Chem., 2006, Vol. 78, No 4, pp. 1349-1356. doi: 10.1016/j.ab.2006.06.026
11.Zhao L., Ai P., Duan AH. et al, Anal. Bioanal. Chem., 2011, No 399, pp. 143-147. doi:10.1007/s00216-010-4079-8
12.Shashkov M.V., Sidelnikov V.N., J. Chromatogr. A., 2013, No 1309, pp. 56-63. 10.1016/j.chroma.2013.08.030
13.Zhang Y., Tu T., Miao C., et al, Advanced Materials Research, 2012, Vol. 518-523, pp. 3989-3992.oi:10.4028/www.scientific.net/AMR.518-523.3989
14.Gas chromatrograph Agilent 7890B, brochure, Agilent Technologies, 2013.
15.Tkachev А.V., Uspekhi khimii, 2007, Vol. 76, No10, pp. 1014-1033.
