Molecular torsion balances: Evidence for favorable orthogonal dipolar interactions between organic fluorine and amide groups

ORGN 264

Felix Raoul Fischer, felix.fischer@org.chem.ethz.ch, W. Bernd Schweizer, and François Diederich, diederich@org.chem.ethz.ch. Department of Chemistry, Swiss Federal Institute of Technology Zurich, Wolfgang-Pauli-Strasse 10, HCI-G312, 8093 Zurich, Switzerland
A newly designed indole-extended molecular torsion balance provides the geometry for the measurement of a truly orthogonal noncovalent interaction between a C-F bond dipole and the face of an amide carbonyl group giving evidence for the attractive nature of orthogonal dipolar interactions. Employing a double-mutant cycle approach, interaction free enthalpies in the range of –0.8 to –1.2 kJ mol-1 were determined, confirming that orthogonal dipolar interactions provide new tools for enhancing the stability of protein-ligand complexes and for assembling supramolecular architectures.

 

Molecular Recognition and Self Assembly
1:00 PM-4:40 PM, Monday, April 7, 2008 Morial Convention Center -- Rm. R04, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008