TITLE

Chiral recognition in NMR spectroscopy using crown ethers and their ytterbium(III) complexes

AUTHOR(S)
Wenzel, Thomas J.; Freeman, Bailey E.; Sek, David C.; Zopf, Jason J.; Nakamura, Takashi; Yongzhu, Jin; Hirose, Keiji; Tobe, Yoshito
PUB. DATE
March 2004
SOURCE
Analytical & Bioanalytical Chemistry;Mar2004, Vol. 378 Issue 6, p1536
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Chiral crown ethers 1 and 5 are useful enantiomeric discriminating agents in 1H NMR spectroscopy for neutral and protonated primary amines, amino acids, and amino alcohols. The presence of the carboxylic acid groups in 1 and 5 provide sites at which ytterbium(III) can bind. Adding ytterbium(III) nitrate to crown–substrate mixtures in methanol-d4 causes shifts in the spectra of substrates and often enhances the chiral discrimination in the 1H NMR spectrum. The enhancement in enantiomeric discrimination that occurs in the presence of ytterbium(III) allows lower concentrations of the crown ether to be used in chiral recognition studies. Several amide derivatives of 1 were prepared and evaluated as chiral NMR discriminating agents, although except for 1e, these were less effective than 1.
ACCESSION #
15124931

 

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