Development of bispidine-derived artificial receptors for organic molecules

ORGN 708

Lauri Toom, Lauri.Toom@kemi.uu.se, Helena Grennberg, and Adolf Gogoll. Department of Chemistry, Organic Chemistry, Uppsala University, Box 599, Uppsala, 75124, Sweden
We have been working on the development of host-guest systems for small organic molecules with the aim to bind these molecules to a host using a metal ion. Ultimately, we want to access structural information of the guest molecule, and to expand the variety of host and guest structures. In the current investigation we describe the synthesis and characterisation of 3,7-diazabicyclo[3.3.1]nonane (bispidine) derivatives, which contain a rigid molecular scaffold. They provide an appropriate arrangement of two nitrogen atoms for chelating a Lewis acid centre that in turn mediates the binding of small guest molecules. The structure and dynamic behaviour of the host-guest complex is then determined by NMR spectroscopy. Valuable information is also obtained from X-ray crystallography and pKa measurements.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005