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NMR Studies of Agricultural Products. Applications of Achiral and Chiral Lanthanide Shi...
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NMR Studies of Agricultural Products. Applications of Achiral and Chiral Lanthanide Shift Reagents to the Fungicide, Triadimefon.
作者:
Elisa Carbonell,
Robert Rothchild,
期刊:
Spectroscopy Letters
(Taylor Available online 1994)
卷期:
Volume 27,
issue 7
页码: 861-878
ISSN:0038-7010
年代: 1994
DOI:10.1080/00387019408006638
出版商: Taylor & Francis Group
关键词: 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-y1)-2-butanone;Optical Purity;Enantiomeric Excess;Stereoisomer;Analysis;Europium;Eu (FOD)3;Eu(HFC)3;LSR;Spiking Experiment;Sense of Magnetic Nonequivalense.
数据来源: Taylor
摘要:
The 60 MHz1H NMR spectra of the systemic agricultural fungicide, triadimefon,1, have been studied in CDCl3at 28±1° (as the racemic free base) with the added achiral lanthanide shift reagent (LSR), tris(6, 6, 7, 7, 8, 8, 8-heptafluoro-2, 2-dimethyl-3, 5-octanedionato) europium(III), Eu(FOD)3,2, for spectral simplification, and with the chiral LSR, tris [3-(heptafluoropropylhydroxymethylene)-(+) -camphorato)europium(III), Eu(HFC)3,3, to induce enantiomeric shift differences (ΔΔδ) for several nuclei. Significant ΔΔδ values were seen for the two protons of the heterocyclic ring, the OCH methine, and aryl H-2′, 6′ of the chlorophenoxy ring. For each of these nuclei exhibiting ΔΔδ with added 3, the ΔΔδ magnitudes reached maximum values with3:1molar ratios ca. 0. 18–0. 29, and decreased with higher levels of3. To confirm analytical utility of 3 for % e. e. determinations of1, a nonracemic (“spiked”) sample of racemic1, with addedR-(−) triadimefon, was examined with3. At low3:1ratios, both triazole H-3 and H-5, as well as the OCH and aryl H-2′, 6′ protons of (−)-1showed a downfield sense of magnetic nonequivalence with (+) -3. With3:1ratios ca. 0. 8, triazole proton H-3 reversed its sense of magnetic noneguivalence. The H-3 and H-5 signals were useful for % e. e determinations at this higher3:1ratio.
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