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1H NMR Spectral Simplification with Achiral and Chiral Lanthanide Shift Reagents. 2-Methyl-3-(2′-Hydroxymethylphenyl)-4(3H)-Quinazolinone, A Major Metabolite of Methaqualone

 

作者: Andrea Poropatich,   Robert Rothchild,  

 

期刊: Spectroscopy Letters  (Taylor Available online 1990)
卷期: Volume 23, issue 1  

页码: 29-43

 

ISSN:0038-7010

 

年代: 1990

 

DOI:10.1080/00387019008054034

 

出版商: Taylor & Francis Group

 

关键词: Europium;Optical Purity;Enantiomer;Eu(FOD)3;Eu(HFC)3;Biaryl Hindered Rotation;Analysis

 

数据来源: Taylor

 

摘要:

The 60 MHz1H NMR spectra of 2-methyl-3-(2′-hydroxymethylphenyl)-4(3H)-quinazolinone,1, a major metabolite of methaqualone, 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, and the chiral reagent tris [3-(heptafluoropropylhydroxy-methylene)-d-camphorato]europium (III),3, Lanthanide induced shifts, Δλ, are consistent with major LSR binding at the hydroxyl, and the diastereotopic hydrogens of the CH2are clearly anisochronous. Substantial Δλ values and spectral simplification are achieved with2or3. Significant enantiomeric shift differences, ΔΔλ, are observed with3that should provide direct optical purity determinations of1. Results are discused in terms of LSR binding sites and hindered rotations about selected bonds in1.

 

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