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  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > November  >
In the Laboratory
Synthesis and Self-Assembly of the "Tennis Ball" Dimer and Subsequent Encapsulation of Methane. An Advanced Organic Chemistry Laboratory Experiment
Fraser Hof, Liam C. Palmer, and Julius Rebek Jr.
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037-1000
Cover
November 2001
Vol. 78 No. 11
p. 1519
Abstract
While important to the biological and materials sciences, noncovalent interactions, self-folding, and self-assembly often receive little discussion in the undergraduate chemistry curriculum. The synthesis and NMR characterization of a molecular "tennis ball" in an advanced undergraduate organic chemistry laboratory is a simple and effective way to introduce the relevance of these concepts. In appropriate solvents, the monomer dimerizes through a seam of eight hydrogen bonds with encapsulation of a guest molecule and symmetry reminiscent of a tennis ball. The entire experiment can be completed in three lab periods, however large-scale synthetic preparation of the starting monomer by a teaching assistant would reduce the laboratory to a single lab period for NMR studies.
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*  Citation
 Hof, Fraser; Palmer, Liam C.; Rebek, Julius, Jr. J. Chem. Educ. 2001 78 1519.
*  Keywords
 Intermolecular Forces; Laboratory Instruction; Molecular Recognition; NMR Spectrometry; Organic Synthesis
*  History
 Created:
Last Updated:		 October 8, 2001
August 31, 2005
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