Dramatic acceleration of the Menshutkin reaction

ORGN 448

Jung-Jae Lee, jlee7@nd.edu1, Keith J. Stanger, kstanger@nd.edu2, and Bradley D. Smith, smith.115@nd.edu1. (1) Department of Chemistry & Biochemistry, University of Notre Dame, 380 Nieuwland Science Hall, Notre Dame, IN 46556-5670, (2) Walther Cancer Institute, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670
The quaternization of a trialkylamine is known as the Menshutkin reaction. The reaction involves an alkyl group transfer, a process of central importance in biochemistry and a widely used strategy in organic synthesis. We have developed a simple macrocyclic amine that undergoes the Menshutkin reaction with dramatically enhanced reactivity. For example, the macrocycle reacts with methylene chloride with a half life of 2 minutes at 25 °C, a rate that is about 50,000 times faster than that observed with structurally related, linear amines. Physical organic and supramolecular chemistry experiments will be described that shed light on the reaction mechanism.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005