On the role of fluorine in intermolecular interactions

COMP 9

Sandro Mecozzi, School of Pharmacy and Department of Chemistry, School of Pharmacy and Department of Chemistry, University of Wisconsin, 777 Highland Ave, Madison, WI 53705
We wish to report on the nature and strength of fluorine-mediated intermolecular forces. Binding energies between representative fluorinated molecules and cations / hydrogen bond donors have been calculated through high level ab initio calculations extrapolated at the complete basis set limit. NBO analysis is then used to provide an explanation for the origin of these interactions. The role of the degree of substitution on the carbon atom bearing a fluorine functionality has also been analyzed. We will provide evidence of the change in the ability of carbon-bound fluorine to engage in intermolecular interactions based upon the nature of the groups attached to the fluorine-bound carbon atom. Quantitative differences in binding abilities of mono-, di-, and trifluoromethyl functionalities will also be discussed along with corresponding applications in drug design and discovery.
 

Computers in Chemistry General
8:20 AM-12:20 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- 104A&B, Oral

Division of Computers in Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004