title: A chromatographic study on the exceptional enantioselectivity of cellulose tris(4-methylbenzoate) towards C5-chiral 4,5-dihydro-(1H)-pyrazole derivatives.
abstract: A set of ten C5-chiral 4,5-dihydro-(1H)-pyrazole derivatives was synthesized and analyzed by high-performance liquid chromatography (HPLC) on the polysaccharide-based Chiralcel OJ-H chiral stationary phase (CSP). The enantioseparations were carried out using pure ethanol as eluent. Different structural elements of the investigated compounds were recognized for obtaining a very high enantioselectivity. In order to clarify some aspects of the chiral discrimination process, the thermodynamic parameters associated to the enantiorecognition and the enantiomer elution order were established.
authors.affiliation: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, I-00161 Rome, Italy. rcirilli@iss.it
authors.forename: Roberto
authors.initials: R
authors.lastname: Cirilli
authors.forename: Stefano
authors.initials: S
authors.lastname: Alcaro
authors.forename: Rossella
authors.initials: R
authors.lastname: Fioravanti
authors.forename: Rosella
authors.initials: R
authors.lastname: Ferretti
authors.forename: Adriana
authors.initials: A
authors.lastname: Bolasco
authors.forename: Bruno
authors.initials: B
authors.lastname: Gallinella
authors.forename: Cristina
authors.initials: C
authors.lastname: Faggi
mesh_terms: D000327:Adsorption; D001565:Benzoates / Q000737:chemistry*; D002482:Cellulose / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001565:Benzoates; D011720:Pyrazoles; C090722:tris(4-methylbenzoate)cellulose; C031280:pyrazole; D002482:Cellulose