Journal
JOURNAL OF SEPARATION SCIENCE
Volume 34, Issue 18, Pages 2391-2396Publisher
WILEY-BLACKWELL
DOI: 10.1002/jssc.201100395
Keywords
Chiral stationary phase; Cinchona alkaloids; Click chemistry; Enantioselective chromatography; Quinine
Categories
Funding
- EU [MEIF-CT-2004-011165]
- MNiSW [N N204 178340]
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A new Pirkle-anion exchange hybrid-type chiral stationary phase (CSP-1) has been synthesized by immobilizing 10,11-didehydroquinine 3,5-dinitrophenylcarbamate onto 3-azidopropyl silica gel using click chemistry (1,3-dipolar Huisgen cycloaddition). This chiral selector and CSP contain a strong pi-accepting 3,5-dinitrophenyl residue besides the pi-basic quinoline group and an ionizable tertiary amino group. In concert with ion pairing it offers pi-donor-pi-acceptor interactions resulting in an enhancement of the selectivity toward specific pi-donating analytes such as aryloxypropionic acids and profens. A representative set of these analytes has been investigated under various chromatographic conditions (polar-organic, reversed-and normal-phase) leading to base-line enantiose-parations with selectivity (alpha) values up to 1.8. Control experiments with related quinine tert-butylcarbamate phase grafted onto the surface either by thioether (Chiralpak QN-AX) or 1,2,3-triazole linker revealed the impact of the additional aromatic moiety in the chiral selector motif.
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