ORGN 590 |
| Byron W. Purse1, Pablo Ballester2, and Julius Rebek Jr.1. (1) The Skaggs Institute for Chemical Biology and The Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Rd. MB-26, La Jolla, CA 92037, (2) Departament de Química, Universitat de les Illes Balears, Crta. Valldemossa Km. 7.5. Edifici Mateu Orfila Campus de la UIB, 07122 Palma de Mallorca, Spain |
| One focus of research in supramolecular chemistry is host molecules with inwardly-directed functional groups. The functional groups of these hosts can direct specificity of guest binding and affect stoichiometric or catalytic chemical reactivity in the host cavity. Our research in the supramolecular chemistry of cavitands has led us to develop a vase-shaped host with a carboxylic acid rigidly oriented in the cavity interior (see figure; one host wall removed for clarity in model). The reactivity of the acid is profoundly influenced by its environment. The acid reacts with carbodiimides at substantially different rates depending on host-guest complementarity. We have also observed that the corresponding methyl ester cavitand quaternizes specific tertiary amines in a methyl transfer reaction at rates greater than 20,000 fold higher than similar reactions without supramolecular effects. The most recent results of our ongoing investigation of the chemistry of this host will be described. |
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Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Thursday, April 1, 2004 Anaheim Convention Center -- 303A, Oral
Division of Organic Chemistry |
