Interaction of a C-F Bond with the π-System of a C=C Bond or Head On with a Proximate C-H Bond

We describe the synthesis and preliminary study of two molecules, in which a fluorine atom is positioned proximately above the pi-orbitals of a C=C bond or else wherein a C-F bond interacts in a head on fashion with a proximate C-H bond. The spectroscopic characteristics of these unusual interactions are documented, X-ray crystallographic analyses are reported, and theoretical calculations are employed to support the observed spectroscopy.