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Determination of the optical purity of some substituted N‐phenylpropionamides by NMR spectroscopy
Author(s) -
Snatzke Günther,
Fox John E.,
ElAbadelah Mustafa M.
Publication year - 1973
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270050905
Subject(s) - moiety , enantiomer , chemistry , solvent , spectral line , chemical shift , nuclear magnetic resonance spectroscopy , nmr spectra database , enantiomeric excess , stereochemistry , organic chemistry , enantioselective synthesis , physics , catalysis , astronomy
The NMR spectra of a series of chiral propionamides have been determined in D(+)1‐phenylethylamine solution. The α‐methine protons of the propionic acid moiety in the propionamide enantiomers were found to be anisochronous in this solvent. The sense of non‐equivalence of these protons was found to be the same for all members of a homochiral series. The chemical shift difference between their signals was demonstrated to be dependent upon the temperature and concentration of the solution. A method is described whereby the enantiomeric purity of the amides could be calculated from these signals in cases where the position of the baseline in their spectra was unknown.