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Citation: WENG Wen, YAO Bi-Xia, YOU Xiu-Li, ZENG Qing-Le. Enantioseparation of BINOL Using l-Tartaric Acid Derivative as Chiral Stationary Phase[J]. Chinese Journal of Applied Chemistry, ;2004, 21(8): 853-855. shu

Enantioseparation of BINOL Using l-Tartaric Acid Derivative as Chiral Stationary Phase

1.
a Department of Chemistry, Zhangzhou Teachers College, Zhangzhou, 363000;
2.
b Chengdu Di'ao Pharmaceutical Company and Department of Pharmacy, Sichuan University, Chengdu

Corresponding author: WENG Wen,
Received Date: 28 August 2003
Available Online: 10 December 2003
Fund Project: 福建省高校重点科技基金项目(JA99210) (JA99210)福建省科技厅三项经费(K02092)资助 (K02092)

1,1'-Bi-2-naphthol(BINOL) enantiomers were baseline resolved on HPLC network-polymeric chiral stationary phase (Kromasil CHI-DMB, based on O,O'-di(3,5-dimethylbenzoyl)N,N'-diallyl-L-tartaric diamide). The effects of the column temperature, the type and the concentration of the polar alcohol modifier in the binary mobile phase on the chiral resolution were examined. The separation value was 1.191 when V(hexane):V(2-propanol)=95:5 was used as mobile phase at a flow rate of 1.0 mL/min at 25℃ with retention time being within 14 minutes. The mechanism of the chiral recognition was discussed with the calculated thermodynamic parameters. It is suggested that hydrogen bonding interaction between hydroxyl group of the solute and the CSP play important roles in chiral recognition. The chiral resolution is enthalpy-entropy driven and the enthalpy contribution is greater. 1,1'-Bi-2-naphthyl di-P-toluenesulfonate, 1,1'-bi-2-naphthyl diacetate and 1,1'-bi-2-naphthyl dicinnamate could not be resolved at experiment conditions used.
- bi-naphthol,
- chiral resolution,
- chiral stationary phase,
- tartaric acid,
- network polymer,
- liquid chromatography
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