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Chiral discrimination of secondary alcohols by both 1 H‐NMR and HPLC after labeling with a chiral derivatization reagent, 2‐(2,3‐anthracenedicarboximide)cyclohexane carboxylic acid
Author(s) -
Ohtaki Takashi,
Akasaka Kazuaki,
Kabuto Chizuko,
Ohrui Hiroshi
Publication year - 2005
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.20141
Subject(s) - chemistry , chiral derivatizing agent , derivatization , enantiomer , high performance liquid chromatography , reagent , alkyl , chirality (physics) , carboxylic acid , cyclohexane , proton nmr , organic chemistry , carbon 13 nmr , chiral column chromatography , chromatography , chiral symmetry , quark , physics , quantum mechanics , nambu–jona lasinio model
Enantiomeric discrimination of chiral secondary alcohols was performed by both reversed‐phase HPLC and 1 H‐NMR after labeling with a chiral fluorescent derivatization reagent, 2‐(2,3‐anthracenedicarboximide)cyclohexanecarboxylic acid. It was possible to discriminate by HPLC the chirality of alcohols up to C30 having a chiral hydroxyl group at the middle of the straight alkyl chain, and, by 1 H‐NMR, alcohols up to C16. For alcohols having one straight alkyl and one isoalkyl group with the same carbon numbers at both sides of a hydroxyl group, it was possible to discriminate the chiralities of alcohols up to C19 by both 1 H‐NMR and HPLC. The 1 H‐NMR methods also made it possible to determine absolute configurations empirically. Chirality 17:S171–S176, 2005. © 2005 Wiley‐Liss, Inc.