title: Novel Pirkle-type quinine 3,5-dinitrophenylcarbamate chiral stationary phase implementing click chemistry.
abstract: 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 π-accepting 3,5-dinitrophenyl residue besides the π-basic quinoline group and an ionizable tertiary amino group. In concert with ion pairing it offers π-donor-π-acceptor interactions resulting in an enhancement of the selectivity toward specific π-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 enantioseparations with selectivity (α) 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.
authors.affiliation: Department of Chemistry, Adam Mickiewicz University, Poznan, Poland. karol.kacprzak@gmail.com
authors.forename: Karol M
authors.initials: KM
authors.lastname: Kacprzak
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Lindner
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D057930:Click Chemistry / Q000379:methods*; D003500:Cyclization; D005782:Gels / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D011812:Quinuclidines / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D005782:Gels; D011804:Quinolines; D011812:Quinuclidines; D012822:Silicon Dioxide