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1H NMR Spectral Simplification with Achiral and Chiral Lanthanide Shift Reagents. Mexiletine

 

作者: HassanY. Aboul-Enein,   Simonique Médonné,   Robert Rothchild,  

 

期刊: Spectroscopy Letters  (Taylor Available online 1991)
卷期: Volume 24, issue 6  

页码: 909-930

 

ISSN:0038-7010

 

年代: 1991

 

DOI:10.1080/00387019108018170

 

出版商: Taylor & Francis Group

 

关键词: Europium;Optical Purity;Enantiomer;Eu(FOD)3;Eu(FACAM)3;Eu(HFC)3;Analysis

 

数据来源: Taylor

 

摘要:

The 60 MHz1H NMR spectra of mexiletine, 1-(2,6-dimethylphenoxy)-2-propanamine,1, have been studied at 28° in CDCl3solution with the achiral reagent, tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato) europium(III),2, Eu(FOD)3, and the chiral reagents tris[3-(trifluoromethylhydroxymethylene)-d-camphorato]europium(III),3, Eu(FACAM)3, and tris[3-(heptafluoropropylhydroxymethylene)-d-camphorato]europium(III),4, Eu(HFC)3. Substantial lanthanide-induced shifts were seen for the proton signals of1with each reagent. Appreciable enantiomeric shift differences were seen for both methyl signals and for each of the CH2CH proton signals using3and4that should permit direct determinations of enantiomeric excess for samples of1. A predominant conformation for1is suggested based on observed splittings of the CH2proton signals and their relative lanthanide-induced shifts.

 

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