We have synthesized and conducted studies on two self-assembled monolayers which have an oxyaniline tail group that is tethered to a gold surface via an alkanethiol chain. Reflection-absorption infrared spectroscopy (RAIRS), electrochemical, and contact angle measurements were performed on pristine 2-(6-mercaptohexan-1-oxy)aniline (AnC6SH) and 2-(7-mercaptoheptan-1-oxy)aniline (AnC7SH) monolayers on planar Au surfaces. The pristine monolayers were electrochemically oxidized in 1 M H2SO4, and the resulting voltammetry was compared to that of dimeric model compounds and electrochemically deposited poly(o-phenetidine) films on Au electrodes, RAIRS and electrochemical data reveal that electrochemical oxidation of AnC6SH and AnC7SH monolayers on Au results in the formation of surface-confined poly(aniline) as well as aniline dimers and hydrolyzed aniline dimers.