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Evaluation of “click” binaphthyl chiral stationary phases by liquid chromatography
Author(s) -
Yu Hui,
Yin Chenghua,
Jia Cunyu,
Jin Yu,
Ke Yanxiong,
Liang Xinmiao
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22039
Subject(s) - chemistry , chiral stationary phase , chromatography , click chemistry , chiral column chromatography , hydrophilic interaction chromatography , high performance liquid chromatography , stationary phase , chirality (physics) , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
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 π–π 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 24:391–399, 2012 . Copyright © 2012 Wiley Periodicals, Inc.