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 (alpha = 204) 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.
This paper describes the results obtained in the HPLC enantioseparation of N-thiocarbamoy1-3-(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 (alpha = 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. (C) 2013 Elsevier B.V. All rights reserved.
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 / Francesco, Ortuso; Stefano, Alcaro; Menta, Sergio; Fioravanti, Rossella; Roberto, Cirilli. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1324:(2014), pp. 71-77. [10.1016/j.chroma.2013.11.020]
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
MENTA, SERGIO;FIORAVANTI, Rossella;
2014
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 (alpha = 204) 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
