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Preparation and application of a chiral stationary phase based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid without extra free aminopropyl groups on silica surface
Author(s) -
Hyun Myung Ho,
Cho Yoon Jae
Publication year - 2005
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200401919
Subject(s) - chemistry , crown ether , silica gel , resolution (logic) , amino acid , lipophilicity , phase (matter) , enantiomer , organic chemistry , chromatography , ion , biochemistry , artificial intelligence , computer science
A crown ether‐based chiral stationary phase (CSP) without extra aminopropyl groups on the surface of silica gel was newly prepared by bonding (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid to silica gel. The new CSP was applied to the resolution of various racemic α‐amino acids, amines, and amino alcohols. The chiral recognition efficiency of the new CSP was generally superior to that of the original CSP containing unreacted residual aminopropyl groups on the surface of silica gel in terms of the separation (α) and the resolution factors ( R S ). The retention behaviors of analytes on the new CSP with the variation of the content of organic and acidic modifiers in aqueous mobile phase were consistent with those on the original CSP in the resolution of α‐amino acids, but somewhat different in the resolution of racemic amines and amino alcohols from those on the original CSP and the difference was rationalized by the lipophilicity difference of the two CSPs. The effect of the column temperature on the chromatographic resolution behaviors on the new CSP was consistent with that on the original CSP.