1H NMR Spectral Simplification with Achiral and Chiral Lanthanide Shift Reagents. Fenimide. Direct Simultaneous Determination of Four Stereoisomers
作者:
Carol Myers,
Robert Rothchild,
期刊:
Spectroscopy Letters
(Taylor Available online 1987)
卷期:
Volume 20,
issue 10
页码: 805-819
ISSN:0038-7010
年代: 1987
DOI:10.1080/00387018708081589
出版商: Taylor & Francis Group
关键词: Lanthanide;NMR Shift Reagent;Fenimide;Europium;Chiral;Optical Purity;Enantiomer;Diastereomer;4-ethyl-3-methyl-3-phenyl-2,5-pyrrolidine-dione
数据来源: Taylor
摘要:
The 60 MHZ1H NMR spectra of racemic commercial fenimide, 4-ethyl-3-methyl-3-phenyl-2,5-pyrrolidine-dioner1, have been studied in CDCl3solution at 28° with the achiral shift reagent, tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato) europium-(III)2, and the chiral reagent, trist3-(heptafluoro-propylhydroxymethy1ene)-d-camphoratol europium(III)3.Use of2substantially increased the chemical shift differences between resonances of corresponding nuclei in thealphaandbetadiastereomers, simplifying mixture analyses. Use of the chiral3produced enantiomeric shift differences, ΔΔΔ for several signals of1.In particular, with a 0.309 molal solution of1and a3:1, molar ratio near 0.4, four distinct singlets can be seen for the quaternary methyl signal. Direct simultaneous analysis for all four stereoisomers (two pairs of enantiomers) should be feasible.
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