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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > January  >
In The Classroom
JCE Featured Molecules
The Chemistry of Highly Fluorinated Compounds
William F. Coleman
Department of Chemistry, Wellesley College, Wellesley, MA 02481
Cover
January 2006
Vol. 83 No. 1
p. 92
Full Text
The featured molecules for January come from the paper “Fluorous Compounds and Their Role in Separation Chemistry” by Maria Angeles Ubeda and Roman Dembinski. This paper explores the use of highly fluorinated compounds as solvents, catalysts, and reagents. Additions to the molecule collection include most of the species from this paper. Students who have access to computational software might be asked to measure barriers to rotation about the bonds attached to the aromatic rings in molecules 1, 3, and 6, or to explore the question of planarity in the center region of molecule 4. The arguments in the paper might also be clearer to students by comparing the charge distribution of the fluorous compound with that of the corresponding perhydro species.

Fully manipulable (Chime and Jmol) versions of the fluorous molecules labeled 1–7 and the reactants and products of Schemes I–V in the article are available at the JCE Digital Library Web site.

Image of molecule.

Figure 1. fluorous phenylboronic acid

Image of molecule.

Figure 2. fluorous alkyl phospine

Image of molecule.

Figure 3. fluorous acid

Image of molecule.

Figure 4. fluorous chlorosilane

Image of molecule.

Figure 5. fluorous reverse-phase silica gel
More Information
*  Citation
 Coleman, William F. J. Chem. Educ. 2006 83 92.
*  Keywords
 Computer-Based Learning; Internet / Web-Based Learning; Molecular Modeling; Molecular Properties / Structure
*  History
 Created:
Last Updated:		 12/1/2005
12/7/2005
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