¹H NMR Spectral Simplification with Achiral and Chiral Lanthanide Shift Reagents. Part III: Vinclozolin

Authors: Hatzis, Alexander; Rothchild, Robert

Source: Applied Spectroscopy, Volume 40, Issue 6, Pages 729-886 (August 1986) , pp. 743-745(3)

Publisher: Society for Applied Spectroscopy

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Abstract:

The 60 MHz ¹H NMR spectra of racemic vinclozolin, 1, have been studied at 28° in CDCl₃ solution with the achiral reagent tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium(III), 2, and the chiral reagents tris[3-(trifluoromethylhydroxymethylene)-d-camphorato] europium(III), 3, and tris[3-(heptafluoropropylhydroxymethylene)-d-camphorato]europium(III), 4. Reagent 3 produced only small lanthanide-induced shifts and no observable enantiomeric shift differences, ΔΔδ, with 3:1 molar ratios as high as 1.40. In contrast, chiral reagent 4 produced substantial ΔΔδ for the proton, H_β, at C-2 of the ethenyl group syn to the oxazolidinedione ring and smaller ΔΔδ for the anti proton, H_β' at the above carbon and for the CH₃. With a 4:1 molar ratio of 0.581, ΔΔδ of 7.0 Hz was seen for H_β. A 4:1 ratio of about 0.41 should be optimum for optical purity determinations; as little as 5% of the minor enantiomer should be detectable.

Keywords: Analysis for optical purity of vinclozolin; Analytical methods; NMR; Achiral and chiral lanthanide shift reagents; Lanthanide shift reagents; Optical purity of vinclozolin; Vinclozolin

Document Type: Research article

DOI: http://dx.doi.org/10.1366/0003702864508359

Affiliations: 1: The City University of New York, John Jay College of Criminal Justice, Department of Science, 445 West 59th Street, New York, New York 10019-1199

Publication date: 1986-08-01

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