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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

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, Sergio Menta, Rossella Fioravanti, Roberto Cirilli

J Chromatogr A. 2014 Jan 10;1324:71-7.

PMID: 24315676

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP50649597	4-Pentylphenyl 4-methylbenzoate		50649-59-7	Price

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