Florobenzene as artificial nucleobases-base pairing and stacking interactions.

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.