NMR Studies of Drugs. Application of a Chiral Lanthanide Shift Reagent for Potential Direct Determination of Enantiomeric Excess of Methsuximide |
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| Authors: | Robert J Reifsneider Jr Bernard H Hoffman Kunisi S Venkatasubban Robert Rothchild Rolf Martin |
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| Institution: | 1. Department of Natural Science , University of North Florida , Jacksonville, FL, 32216;2. The City University of New York, John Jay College of Criminal Justice, Toxicology Research and Training Center, Department of Science , 445 West 59th Street, New York, NY, 10019-1199;3. Chemistry Department , West Virginia State College, Institute , WV, 25112 |
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| Abstract: | The 200 MHz 1H NMR Spectra of methsuximide, 1,3-dimethy1-3-ogebt1-2,5-otrrikudubeduibem 1, havebeen studied in CDC13 solution with the chiral reagent, tris3-(heptafluoropropy1-hydroxymethylene)-d-camphorato] europium (III), 2, Eu(HFC)3. Substantial lanthanide-induced shifts are seen. In addition, significant enantiomeric shift differences are observed for several of the nuclei of 1. With a 2:1 molar ratio near 1.0, the CCH3 and NCH3 signals show nearly baseline resolution between the peaks from each enantiomer, providing excellent potential for direct determinations of enantiomeric excess of samples of 1. As little as 2% of a minor enatiomer should be readily detectable. |
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| Keywords: | Europium Eu(HFC)3 Optical Purity Analysis Anticonvulsant 1H NMR succinimides |
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