Sulfur and selenium act as “alligator clips” for the attachment of molecular electronics via chemisorption to gold. There have been reports in the literature debating which attachment more effectively facilitates electron transfer. Reactive Ion Scattering Spectrometry (RISS) was used to investigate self-assembled monolayers (SAMs) formed from symmetric disulfides and diselenides. RISS utilizes a tandem quadrupole mass spectrometer to select ions of a given mass-to-charge value and collides them with a specified collision energy into the surface. All resulting ions from these collisions are recorded as a total scattered ion current (TIC) which is inversely related to the amount of ions neutralized by electron transfer at the surface. Based on previous studies, we have found that the electron transfer properties of alkylthiolate SAMs differ from those of semifluorinated thiolate SAMs. This study will look at the corresponding chain lengths of alkyl as well as semifluorinated functionalized disulfide and diselenide SAMs. Through these experiments, direct evidence can be gained on the electron transfer properties of these films on a single gold electrode. In addition, RISS will be used to characterize the SAM films based on the amount of energy deposited into impinging projectile ions as well as the amount of reactive terminal group abstractions resulting from collisions. The dependence of film formation on solvent will also be reported with respect to the amount of electron transfer exhibited and overall characterization of the films.