Chromatographic enantioseparations of binaphthyl compounds on an immobilized polysaccharide-based chiral stationary phase

Seven binaphthyl compounds were enantioseparated by HPLC with an immobilized polysaccharide-based chiral stationary phase, Chiralpak IA. The experiments were performed under normal-phase conditions. Effects of polar modifier and column temperature on the retention time and separation factor were evaluated. All examined compounds obtained complete resolutions. This was the unique one ever reported that 1,1′-bi-2-naphthol and its monoether, diether and diester derivatives could all be enantioseparated on a given CSP. Apparent thermodynamic parameters were also deduced from Van’t Hoff plots, and some aspects of chiral recognition mechanism were discussed further.