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Crystallographic studies for the chiral recognition of the novel chiral stationary phase derived from (+)‐(R)‐18‐crown‐6 tetracarboxylic acid
Author(s) -
Machida Yoshio,
Nishi Hiroyuki,
Nakamura Kouji
Publication year - 1999
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/(sici)1520-636x(1999)11:3<173::aid-chir1>3.0.co;2-p
Subject(s) - chemistry , enantiomer , ethylamine , chirality (physics) , crystallization , hydrogen bond , crystal structure , elution , 18 crown 6 , crystallography , ring (chemistry) , chiral resolution , phase (matter) , stereochemistry , molecule , organic chemistry , chromatography , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Chiral discrimination observed in high‐performance liquid chromatography (HPLC) with the novel chiral stationary phase (CSP‐18C6I) derived from (+)‐(R)‐18‐crown‐6 tetracarboxylic acid [(+)‐18C6H 4 ] was investigated by X‐ray crystallographic analysis of the complex composed of the R‐enantiomer of 1‐(1‐naphthyl)ethylamine (1‐NEA) and (+)‐18C6H 4 . Mixtures of 1‐NEA (the R‐ or S‐enantiomer) and (+)‐18C6H 4 were dissolved in methanol‐water (1:1) solution and allowed to stand for crystallization. The R‐enantiomer crystallized with (+)‐18C6H 4 as a co‐crystal, although the S‐enantiomer did not. This result was in good agreement with the enantiomer elution order of 1‐NEA in CSP‐18C6I. The apparent binding constants ( K a ) of the enantiomers to the (+)‐18C6H 4 obtained from 1 H‐NMR experiments also supported the above‐mentioned result. The X‐ray crystal structure of the 1:1 complex of the R‐enantiomer and (+)‐18C6H 4 indicated the four sets of hydrogen bond association between the naphthylethylammonium cation and oxygen of polyether ring or carbonyl group of (+)‐18C6H 4 . Chirality 11:173–178, 1999. © 1999 Wiley‐Liss, Inc.