NMR Studies of Drugs. Applications of Achiral and Chiral Lanthanide Shift Reagents to the Anticonvulsant, Methetoin, 5-Ethyl-1-Methyl-5-Phenyl-2, 4-Imidazolidinedione
作者:
Diana Shields,
Han Tran,
KunisiS. Venkatasubban,
Robert Rothchild,
Helen Wyss,
期刊:
Spectroscopy Letters
(Taylor Available online 1994)
卷期:
Volume 27,
issue 1
页码: 23-39
ISSN:0038-7010
年代: 1994
DOI:10.1080/00387019408002505
出版商: Taylor & Francis Group
关键词: 1H NMR;LSR;Europium;Eu(FOD)3;Eu(HFC)3;NMR shift reagents;Lanthanide;Stereoisomers;Enantiomeric excess;Analysis;5-Ethyl-l-methyl-5-phenylhydantoin;Hydantoins
数据来源: Taylor
摘要:
The 200 MHz1H NMR spectra of the anticonvulsant, methetoin,1, have been studied in CDCI3solution at ambient temperatures in the presence of the achiral lanthanide shift reagent tris(6, 6, 7, 7, 8, 8, 8-heptafluoro-2, 2-dimethyl-3, 5-octanedionato) europium(III),2, and the chiral reagent, tris[3-(heptafluoropropylhydroxymethylene)-(+)-camphorato] europium(III),3., With added 1, appreciable enantiomeric shift differences, ΔΔδ, can be induced for the aryl protons and both methyl groups of1. In particular, using3:1molar ratios from ca. 1.2–2, with 0.046 molar1, signals from theCH3CH2and the phenylorthoprotons for the enantiomers of 1 are well resolved, exhibiting excellent potential for direct determinations of enantiomeric excess of1. Relative magnitudes of lanthanide-induced shifts for the different nuclei of 1 with added2or3are compared and discussed.
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