DICP OpenIR
Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography
Yu, Hui1; Yin, Chenghua1; Jia, Cunyu1; Jin, Yu1; Ke, Yanxiong1; Liang, Xinmiao2
KeywordChiral Stationary Phases Click Chemistry Binaphthyl P-p Interaction Thermodynamic Parameters
Source PublicationCHIRALITY
2012-05-01
DOI10.1002/chir.22039
Volume24Issue:5Pages:391-399
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Life Sciences & Biomedicine ; Physical Sciences
WOS SubjectChemistry, Medicinal ; Chemistry, Analytical ; Chemistry, Organic ; Pharmacology & Pharmacy
WOS Research AreaPharmacology & Pharmacy ; Chemistry
WOS KeywordSILICA-GEL ; EFFICIENT RESOLUTION ; ACID-DERIVATIVES ; ENANTIOSEPARATION ; SEPARATION ; ENANTIOMERS ; RECOGNITION ; TEMPERATURE ; MECHANISM ; BINOL
AbstractTwo 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.
Language英语
WOS IDWOS:000303237200006
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/143073
Collection中国科学院大连化学物理研究所
Affiliation1.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
GB/T 7714
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.
APA Yu, Hui,Yin, Chenghua,Jia, Cunyu,Jin, Yu,Ke, Yanxiong,&Liang, Xinmiao.(2012).Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography.CHIRALITY,24(5),391-399.
MLA Yu, Hui,et al."Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography".CHIRALITY 24.5(2012):391-399.
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