Resolution of enantiomeric aromatic alcohols on a cellulose tribenzoate high-performance liquid chromatography chiral stationary phase : A proposed chiral recognition mechanism

✍ Scribed by Irving W. Wainer; Rose M. Stiffin; Tohru Shibata

• Publisher: Elsevier Science
• Year: 1987
• Tongue: English
• Weight: 927 KB
• Volume: 411
• Category: Article
• ISSN: 1873-3778
• DOI: 10.1016/s0021-9673(00)93965-7

✦ Synopsis

The study investigates the chiral recognition mechanism for the stereochemical resolution of enantiomeric aromatic alcohols on a commercially available cellulose tribenzoate high-performance liquid chromatography chiral stationary phase. A series of chiral and achiral aromatic alcohols were chromatographed and their structural differences related to the chromatographic results. Series of primary and secondary alcohols were also used as mobile phase modifiers to investigate the effect of the steric structure of these modifiers on the capacity factor and stereoselectivity.

The results of this investigation indicate that the chiral recognition mechanism for the enantiomeric aromatic alcohols studied involves: (1) the formation of diastereomeric solute-chiral stationary phase (CSP) complexes through a hydrogen bonding interaction between the solute's alcoholic hydrogen and an ester carbonyl on the CSP;

(2) the stabilization of this complex through the insertion of the aromatic portion of the solute into a chiral cavity (or ravine) of the CSP; and (3) chiral discrimination between enantiomeric solutes due to difference in their steric fit in the chiral cavity.