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Discrimination of enantiomers by means of NMR spectroscopy using chiral liquid crystalline solution: application to triazole fungicides, uniconazole and diniconazole.

Sugiura M, Kimura A, Fujiwara H

Kobe Pharmaceutical University, 4-19-1 Motoyama-kitamachi, Higashinada-ku, Kobe 658-8558, Japan. makiki-s@kobepharma-u.ac.jp

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-gamma-benzyl-L-glutamate)--CDCl3 chiral liquid crystalline solvent for measurements of 13C 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 1S and R, and 2R, and the results are discussed.

Published 11 January 2006 in Magn Reson Chem, 44(2): 121-6.
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