1H NMR Spectral Simplification with Achiral and Chiral Lanthanide Shift Reagents. Meparfynol, 3-Methyl-L-Pentyn-3-Ol. Apparent Anomalous Results with a Binuclear Shift Reagent |
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Authors: | Carol Myers Robert Rothchild |
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Affiliation: | The City University of New York John Jay College of Criminal Justice, Department of Science Toxicology Research and Training Center , 445 West 59th Street, New York, NY, 10019-1199 |
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Abstract: | The 60 MHz 1H NMR spectra of racemic meparfynol, 1, have been studied in CDCl3 solution at 28° with the achiral shift reagentt tris(6,6,7,7,8,8,8-hepta-fluoro-2,2-dimethyl-3,5-octanedionato) europium (III), 2, and the chiral reagent, tris[3-(heptafluoropropyl-hydroxymethylene)-d-camphorat01 europium(III), 3. With 3, observable enantiomeric shift differences for the 3-methyl should make possible direct optical purity determinations. Additions of increments of (6,6,7,7,8,8,8-heptafluoro-2,2-dimenthyl-3,5-octane-dionato)silver(I) 4, to a CDCl3 solution of 1 and 3 resulted in changes in Δδ magnitudes and in some line intensities that are discussed in terms of interactions with the ethynyl and hydroxyl groups. |
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Keywords: | Meparfynol Lanthanide NMR, Shift Reagents Binuclear Silver Optical Purity Enantiomers Chiral |
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