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1999
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Chemical Education Today
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NSF Highlights
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Organic Chemistry Course Development in a Forensic Science Program: Use of FT-NMR
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Ronald Callahan
Chemistry Department, New York University, New York, NY 10003
Lawrence Kobilinsky
John Jay College, New York, NY 10019
Robert Rothchild
John Jay College, New York, NY 10019
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October 1999
Vol. 76 No. 10
p. 1332
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| Abstract |
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The acquisition of a modern, multinuclear, medium-field (7 tesla) FT-NMR, with partial support from NSF-ILI, has made possible the introduction of a major special project for second-semester organic chemistry laboratory, within a forensic science program. The eight-week special project focuses on microscale syntheses of Diels-Alder adducts of phencyclone. Students synthesize a wide range of different N-substituted maleimides for use as dienophiles. The corresponding phencyclone adducts permit studies of: a) unusual hindered rotations of unsubsituted bridgehead phenyls, b) striking examples of magnetic anisotropic effects, and c) modern one- and two-dimensional NMR methods for structural characterization. Use of fluorine-containing dienophiles provides a basis for examining NMR spectra of three different NMR-active nuclei: proton, carbon-13, and fluorine-19. Variable-temperature NMR is also applicable to these compounds. Molecular modeling software has been introduced in the organic laboratory course for students to examine the geometry of these adducts, precursors, and simplified model compounds, and to evaluate geometric parameters in structures that are optimized by semi-empirical and ab initio calculations.
References are included with the article and can be accessed via its PDF file.
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| More Information |
 Citation |
Callahan, Ronald; Kobilinsky, Lawrence; Rothchild, Robert. J. Chem. Educ. 1999 76 1332.
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Keywords |
NMR Spectrometry; Organic Chemistry; Organic Synthesis; Microscale; Molecular Modeling / Dynamics; Stereochemistry; Forensic Chemistry
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History |
Created:
Last Updated: |
September 6, 1999
June 23, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1999
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October
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1332
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