title: A chromatographic and computational study on the driving force operating in the exceptionally large enantioseparation of N-thiocarbamoyl-3-(4'-biphenyl)-5-phenyl-4,5-dihydro-(1H) pyrazole on a 4-methylbenzoate cellulose-based chiral stationary phase.
abstract: This paper describes the results obtained in the HPLC enantioseparation of N-thiocarbamoyl-3-(4'-biphenyl)-5-phenyl-4,5-dihydro-(1H) pyrazole on a cellulose tris(4-methylbenzoate) chiral stationary phase (OJ-3 CSP) using normal-phase and polar organic conditions. The enantioseparation factor (α=207) observed using the mixture n-hexane-2-propanol 70:30 as a mobile phase is among the highest values ever reported in enantioselective HPLC. The enantioseparation process was investigated by means of molecular modelling techniques. Chromatographic and theoretical investigations addressed the extreme affinity of the most CSP retained (S)-enantiomer to the intermolecular H bond network between the ligand thioamide group and the stationary phase O atoms.
authors: Dipartimento di Scienze della Salute, Università "Magna Græcia" di Catanzaro, Campus Universitario "S. Venuta", Viale Europa, 88100 Catanzaro, Italy.
authors: Francesco
authors: F
authors: Ortuso
authors: Dipartimento di Scienze della Salute, Università "Magna Græcia" di Catanzaro, Campus Universitario "S. Venuta", Viale Europa, 88100 Catanzaro, Italy.
authors: Stefano
authors: S
authors: Alcaro
authors: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale A. Moro 5, I-00185 Rome, Italy.
authors: Sergio
authors: S
authors: Menta
authors: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale A. Moro 5, I-00185 Rome, Italy.
authors: Rossella
authors: R
authors: Fioravanti
authors: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, I-00161 Rome, Italy. Electronic address: rcirilli@iss.it.
authors: Roberto
authors: R
authors: Cirilli
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002482:Cellulose / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D008958:Models, Molecular; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D001565:Benzoates; D011720:Pyrazoles; C031280:pyrazole; D002482:Cellulose; C009504:4-toluic acid
keywords: Chiral stationary phase; Chiralcel OJ-3; Enantiomer separation; High enantioselectivity; Molecular dynamics; Temperature effects