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题名: Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography
作者: Yu, Hui1;  Yin, Chenghua1;  Jia, Cunyu1;  Jin, Yu1;  Ke, Yanxiong1;  Liang, Xinmiao2
关键词: chiral stationary phases ;  click chemistry ;  binaphthyl ;  p-p interaction ;  thermodynamic parameters
刊名: CHIRALITY
发表日期: 2012-05-01
DOI: 10.1002/chir.22039
卷: 24, 期:5, 页:391-399
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Life Sciences & Biomedicine ;  Physical Sciences
类目[WOS]: Chemistry, Medicinal ;  Chemistry, Analytical ;  Chemistry, Organic ;  Pharmacology & Pharmacy
研究领域[WOS]: Pharmacology & Pharmacy ;  Chemistry
英文摘要: Two click binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatography. Their structures incorporate S-(-)-1,1'-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of racemic BINOL derivatives, particularly for nonpolar diether derivatives and 3-phenyl indolin-2-one analogs. The chromatographic data showed that the pp interaction was crucial for enantiorecognition of these CSPs. Loss of enantioselectivity observed on CSP3, which are lacking the triazole ring linkage, indicated that the triazole ring linkage took part in the enantioseparation process, although it was remote from the chiral selector of the CSP. The substitution of the phenyl group at 6 and 6' positions can significantly improve the separation ability of the CSP. The chiral recognition mechanism was also investigated by tracking the elution orders and studying the thermodynamic parameters. Chirality 24:391399, 2012. Copyright (c) 2012 Wiley Periodicals, Inc.
关键词[WOS]: SILICA-GEL ;  EFFICIENT RESOLUTION ;  ACID-DERIVATIVES ;  ENANTIOSEPARATION ;  SEPARATION ;  ENANTIOMERS ;  RECOGNITION ;  TEMPERATURE ;  MECHANISM ;  BINOL
语种: 英语
WOS记录号: WOS:000303237200006
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/143073
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.E China Univ Sci & Technol, Sch Pharm, Minist Educ, Engn Res Ctr Pharmaceut Proc Chem, Shanghai 200237, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian, Peoples R China

Recommended Citation:
Yu, Hui,Yin, Chenghua,Jia, Cunyu,et al. Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography[J]. CHIRALITY,2012,24(5):391-399.
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