Florobenzene as Artificial Nucleobases-Base Pairing and Stacking Interactions

Abstract

Base stacking is a complicated and not completely understood phenomenon that is influenced by contributions of electrostatic (dipole-dipole and dipole-induced dipole) interactions, dispersion (permanent dipole–induced dipole) effects and solvation effects. The plots of those factors did not show qualitative correlation (Guckian et al., J. Am. Chem. Soc. 1996, 118, 8182–8183). We tried to correlate the stacking and solvation contributions with lipophilicity, extent of fluorine substitution and dipole moment.

Keywords:

• RNA
• fluorine
• fluorine interactions
• duplex stability
• molecular modeling

Acknowledgments

The work was supported by the DFG Sonderforschungsbereich 579.

Notes

^a Modification is incorporated as X and complementary base for analogues is uridine.^{[ 3 ]}