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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > April  >
In the Classroom
JCE Featured Molecules
Microwave-Assisted Heterocyclic Chemistry
William F. Coleman
Department of Chemistry, Wellesley College, Wellesley, MA 02481
Cover
April 2006
Vol. 83 No. 4
p. 621
Full Text
The featured molecules for this month come from the Green Chemistry article, "Microwave-Assisted Heterocyclic Chemistry for the Undergraduate Organic Laboratory" by Musiol, Tyman-Szram, and Polanski. The authors give conditions and yields for the solid-phase synthesis of a number of heterocyclic compounds in a microwave oven. Although the jury is still out on the detailed mechanism behind microwave acceleration of reaction rates, there is a great deal of interest in such reactions in the chemical community. Students encountering heterocyclic species for the first time might find it useful to consider the effect of addition of a heteroatom on the electron distribution in the molecule. The Chime plug-in enables the user to construct a qualitative electrostatic potential map, allowing students to visualize this map in three-dimensions. Details of this process are available as Supplemental Material.

Fully manipulable (Chime and Jmol) versions of these molecules are available at the JCE Digital Library Web site.

Image of molecule.

Figure 1. benzimidazole

Image of molecule.

Figure 2. succinic anhydride

Image of molecule.

Figure 3. phthalimide

Image of molecule.

Figure 4. piperazine-2,5-dione

Image of molecule.

Figure 5. 2,3-diphenylquinoxaline

Image of molecule.

Figure 6. 5,5-diphenylhydantoin

Image of molecule.

Figure 7. benzoxazinone
Supplement
Details of the process of using Chime to construct a qualitative electrostatic potential map are available here [Macromedia Flash video].
More Information
*  Citation
 Coleman, William F. J. Chem. Educ. 2006 83 621.
*  Keywords
 Computer-Based Learning; Heterocycles; Internet / Web-Based Learning; Molecular Modeling; Molecular Properties / Structure
*  History
 Created:
Last Updated:		 2/24/2006
3/6/2006
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