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| Home > JCE Print > Journal of Chemical Education > Issues >
2007
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March
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In the Laboratory
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Nuclear Overhauser Effect Spectroscopy. An Advanced Undergraduate Experiment
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Michael T. Huggins and Freida Billimoria
Department of Chemistry, University of West Florida, Pensacola, FL 32514
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March 2007
Vol. 84 No. 3
p. 471
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| Abstract |
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The stereochemical features of molecules can have far reaching effects in many areas of science including medicinal chemistry, materials chemistry, and supramolecular chemistry. There have been many techniques developed over the years to determine the absolute configuration of alkenes: the R,S configuration of chiral centers and the most stable conformation of molecules. Yet, very few of these techniques are normally taught in an undergraduate chemistry course. Nuclear Overhauser effect (NOE) spectroscopy has become an essential tool in stereochemical analysis, and with the evolution of the NMR spectrometer, it has become increasingly easier to acquire NOE data. As such, an advanced laboratory experiment has been designed that allows students to use NOESY spectroscopy to conduct conformational analysis studies. In this experiment, students prepare a set of compounds used to study both the configuration of a newly formed double bond (E or Z) and the conformation of the molecule. Using a simple procedure, a wide array of target molecules are prepared, usually in excellent yields. In addition to the configuration of the double bond, the target molecules possess only a single degree of rotational freedom thus simplifying the conformational analysis. Thus, each of the target molecules has four significant spatial arrangements: two configurational isomers with two major conformations of each configuration.
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| Supplement |
Instructions for the students, notes for the instructors, and NMR data (1H and NOESY spectra) for seven target compounds are available.
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| More Information |
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Citation |
Huggins, Michael T.; Billimoria, Freida. J. Chem. Educ. 2007 84 471.
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Keywords |
Alkenes; Conformational Analysis; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Molecular Modeling; NMR Spectroscopy; Organic Chemistry; Stereochemistry; Synthesis; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
2/1/2007
2/22/2007
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 Caution! | | Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations. |
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2007
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471
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