色谱

色谱

• 研究论文 • 上一篇    下一篇

高效液相色谱法手性分离联萘二酚苯甲酸酯对映体

王丽莉, 徐小静, 陈贵阳, 阮源萍*   

  1. 厦门大学化学化工学院化学系, 分析化学重点实验室, 福建 厦门 361005
  • 收稿日期:2009-08-20 修回日期:2009-10-20 出版日期:2010-03-28 发布日期:1981-03-25
  • 通讯作者: 阮源萍

Enantioseparation of 1,1′-bi-2-naphthol benzoates using high performance liquid chromatography

WANG Lili, XU Xiaojing, CHEN Guiyang, RUAN Yuanping*   

  1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Key Laboratory of Analytical Chemistry, Xiamen 361005, China
  • Received:2009-08-20 Revised:2009-10-20 Online:2010-03-28 Published:1981-03-25
  • Contact: RUAN Yuanping

PDF

602

被引次数

10

摘要： 采用Chirex (S)-LEU & (S)-NEA、Chiralcel OD-H和Chiralpak AD-H手性色谱柱直接拆分了2′-羟基-1,1′-联萘-2-苯甲酸酯(HBNB)、1,1′-联萘-2,2′-二苯甲酸酯(BNDB)和2′-甲氧基-1,1′-联萘-2-苯甲酸酯(MBNB)对映体。分别考察了流动相组成、柱温和化合物结构对手性分离的影响。结果表明: 3对联萘二酚苯甲酸酯对映体在Chiralpak AD-H柱上的拆分效果最好。当采用正己烷/异丙醇(40/60, v/v)为流动相时,HBNB、BNDB和MBNB对映体的分离因子(α)和分离度(Rs)分别为1.76、1.74、1.40和6.47、7.81、4.75。对比联萘二酚(BN)的分离,从联萘分子中2-位取代基、对映体出峰顺序和热力学参数等方面探讨了相关手性分离机理。

关键词: 对映体分离, 高效液相色谱法, 联萘二酚苯甲酸酯 , 手性固定相

Abstract: The enantioseparations of 2′-hydroxy-1,1′-binaphthyl-2-yl benzoate (HBNB), 1,1′-binaphthyl-2,2′-diyl dibenzoate (BNDB) and 2′-methoxy-1,1′-binaphthyl-2-yl benzoate (MBNB) were studied on Chirex (S)-LEU & (S)-NEA, cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD-H) and amylose tris(3,5-dimethylphenyl- carbamate) (Chiralpak AD-H) columns, respectively, using high performance liquid chromatography. The effects of mobile phase, column temperature and compound structures on the enantioseparations were discussed. The Chiralpak AD-H exhibited stronger capability of enantioseparation in comparison with those of Chirex (S)-LEU & (S)-NEA and Chiralcel OD-H for 1,1′-bi-2-naphthol benzoates. When using the mobile phase of n-hexane/2-propanol (40/60, v/v), the chiral selectivities of HBNB, BNDB and MBNB were 1.76, 1.74, and 1.40, respectively. Moreover, in comparison with that of 1,1′-bi-2-naphthol (BN), the mechanisms of the enantioseparation of 1,1′-bi-2-naphthol benzoates, related to the substituted groups at 2-position, the elution orders and thermodynamic parameters were also discussed.

Key words: 1,1′-bi-2-naphthol benzoates , chiral stationary phase, enantioseparation, high performance liquid chromatography (HPLC)