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Discrimination of enantiomers by means of NMR spectroscopy using chiral liquid crystalline solution: application to triazole fungicides, uniconazole and diniconazole
Author(s) -
Sugiura Makiko,
Kimura Atsuomi,
Fujiwara Hideaki
Publication year - 2006
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1731
Subject(s) - chemistry , enantiomer , triazole , chemical shift , proton nmr , carbon 13 nmr , chiral derivatizing agent , liquid crystal , organic chemistry , chiral column chromatography , physics , optics
An NMR method for discriminating among enantiomers by using a chiral liquid crystalline solution was applied to chiral triazole compounds, uniconazole (1) and diniconazole (2), which exhibit antifungal and plant growth regulating activities. These chiral compounds were dissolved in PBLG (poly‐γ‐benzyl‐ L ‐glutamate)—CDCl 3 chiral liquid crystalline solvent for measurements of 13 C NMR. The enantiomeric separations were primarily observed in the signals of aromatic carbons owing to differences in chemical shift anisotropies. The enantiomeric excess (ee) was determined from the integral scale of the separated peaks. The resulting ee values are in fair agreement with the actual values. The extrasplittings due to residual dipolar couplings were also measured using Het2DJ spectra for 1 S and R , and 2 R , and the results are discussed. Copyright © 2005 John Wiley & Sons, Ltd.