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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > June  >
Information, Textbooks, Media, Resources
Featured Molecules
Coumarin, Naphthalene, and Additional Polycyclic Aromatic Hydrocarbons
William F. Coleman
Chemistry Department, Wellesley College, Wellesley, MA 02481

Cover
June 2004
Vol. 81 No. 6
p. 912

Full Text
The featured molecules this month are drawn from two papers. The first, “One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water”, is a Green Chemistry feature by Fringuelli, Piermatti, and Pizzo. The three-dimensional versions of the molecules in the synthesis of the coumarin derivative are directly tied to the reaction scheme included in the paper, opening the possibility of showing large numbers of complex synthetic pathways in this manner.

The second paper is “Determining the Carbon–Carbon Distance in an Organic Molecule with a Ruler” by Simoni, Tubino, and Ricchi. This article describes an experiment to determine the size of a naphthalene molecule, using an extension of classic experiments for determining molecular size and Avogadro’s number. While the structure of naphthalene will come as no surprise to most students, the molecule collection also includes additional polycyclic aromatic hydrocarbons (PAHs) that can be used to introduce students to the environmental and health issues related to these molecules.

Fully manipulable (Chime) versions of these molecules appear below. These and other molecules are available at Only@JCE Online.

Image of molecule.

Figure 1. 2,4-dihydroxybenzaldehyde molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 2. 7-hydroxy-3-carboxycoumarin molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 3. Naphthalene molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 4. Phenanthrene molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Figure 5. Anthracene molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

More Information
*  Citation
Coleman, William F. J. Chem. Educ. 2004 81 912.
*  Keywords
Aromaticity / Aromatics; Internet / Web-Based Materials; Molecular Modeling / Dynamics; Molecular Properties / Structure
*  History
Created:
Last Updated:
May 2, 2004
January 28, 2005
  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > June  > Page 912


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