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Enantiomeric discrimination of pyrethroic acid esters on polysaccharide derived chiral stationary phases
Author(s) -
Kim ByoungHyoun,
Lee Sang Uck,
Kim Kun Tai,
Lee JooYoung,
Choi Nak Hee,
Han YoungKyu,
Ok Jong Hoa
Publication year - 2003
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.10195
Subject(s) - chemistry , enantiomer , cellulose , chromatography , carbamate , chirality (physics) , steric effects , hexane , hydrogen bond , organic chemistry , resolution (logic) , enantiomeric excess , tris , enantioselective synthesis , molecule , biochemistry , artificial intelligence , computer science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , catalysis
Enantiomeric separation of pyrethroic acid methyl and ethyl esters was examined on cellulose‐based chiral stationary phases (CSPs): chiralcel OD (cellulose tris(3,5‐dimethylphenyl carbamate)) and chiralcel OF (cellulose tris(4‐chlorophenyl carbamate)). The good resolution of pyrethroic acid esters was achieved on chiralcel OD and OF. Separation factors ranged from 1.19–5.12 for Chiralcel OD and 1.00–1.59 for chiralcel OF. Hexane/2‐propanol (100:0.15, v/v %) was used as the eluent. The resolution capability of CSPs was greater chiralcel OD than chiralcel OF in the case of the pyrethroic acid esters. The flow rate was 0.8 ml/min and detection was set at 230 nm. The results of the chromatographic data and molecular mechanics suggest that steric effect was a major factor in the enantioseparation. Furthermore, the hydrogen bond between analytes and CSP played an important role in the chiral recognition. Chirality 15:276–283, 2003. © 2003 Wiley‐Liss, Inc.