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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > January  >
In the Laboratory
JCE Featured Molecules
Molecular Model of trans-3-(9-Anthryl)-2-Propenoic Acid Ethyl Ester
William F. Coleman
Department of Chemistry, Wellesley College, Wellesley, MA 02481
Cover
January 2007
Vol. 84 No. 1
p. 121

Full Text
The Featured Molecules this month come from the paper by Nguyen and Weisman on solvent-free Wittig reactions and the stereochemical consequences of crowding in the transition state. The molecules include those pictured in the paper as well as the cis isomer of 3-(9-anthryl)-2-propenoic acid ethyl ester. All structures were optimized at the B3LPY/6-31G* level. In the case of ethyl cinnamate, the cis isomer is slightly more stable thermodynamically than the trans isomer, lending further support for the argument that the observed product distribution arises from the energetics of the transition state.

trans-3-(9-Anthryl)-2-propenoic acid ethyl ester

Fully manipulable (Chime and Jmol) structures of trans-3-(9-Anthryl)-2-propenoic acid ethyl ester, trans-cinnamate, and other molecules in the collection are available at the JCE Digital Library Web site.

More Information
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Citation
Coleman, William F. J. Chem. Educ. 2007, 84, 121.
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Keywords
Hands-On Learning / Manipulatives; Molecular Mechanics / Dynamics; Molecular Modeling; Molecular Properties / Structure; Organic Chemistry; Second-Year Undergraduate
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History
Created:
Last Updated:
12/5/2006
3/20/2007
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