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.
Weng
Wen
W
Department of Chemistry and Environmental Science, Zhangzhou Normal University, Zhangzhou 363000, China. weng_wen@126.com
Guo
Hongxu
H
Zhan
Fengping
F
Fang
Hongli
H
Wang
Qingxiang
Q
Yao
Bixia
B
Li
Shunxing
S
D000433:1-Propanol / Q000737:chemistry; D000688:Amylose / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D009284:Naphthols / Q000737:chemistry / Q000302:isolation & purification*; D048448:Phenylcarbamates / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
D009284:Naphthols; D048448:Phenylcarbamates; D012997:Solvents; C080033:Chiralpak AD; C412332:1,1'-bi-2-naphthol; D000688:Amylose; D000433:1-Propanol