Due presumably to the capricious nature of the electrode surface, solid electrode techniques have emerged more slowly than the electrochemical methods employing mercury 1. The consequence of this retarded development has been that the knowledge of anodic oxidations has noticeably lagged behind that of cathodic processes. This is most apparent when one notes that Hoytink's2 classical studies of aromatic hydrocarbon reductions took place during the middle fifties whereas an understanding of the oxidation of these compounds did not develop until the middle sixties 3-7. Many aspects of these electrode processes still remain controversial s-x 1. With the thought in mind of extending the information gained in the study of aromatic hydrocarbon oxidations to other aromatic nuclei, the investigation of the anodic behavior of several aromatic mono-and diazines was undertaken.
The anodic behavior of these compounds is of current interest since pyridine and its homologues are being used as model nucleophiles in the study of anodic substitution reactions12 -18 and pyridine itself has been found to possess interesting and useful properties as an electrochemical solvent 19. The electrochemical oxidation of these compounds has not been studied previously, and furthermore the suggestion that these compounds could not be anodically oxidized by conventional means 2ยฐ seemed questionable and worthy of further study.
The approach to this problem was first to survey the anodic voltammetry of several mono-and diazines using the conventional techniques of cyclic voltammetry and voltammetry at the rotated disk electrode. These studies were intended to determine whether'or not the compounds could be oxidized electrochemically and if so, to characterize that oxidation as chemically reversible or as one complicated by reaction(s) following charge transfer such as an e.c. or e.c.e, reaction scheme 21. With the survey completed, a representative molecule was selected for a more extensive characterization. Acridine was an obvious choice because of the abundance of research 22"23 which has been carried out on this molecule and its derivatives due to their chemotherapeutic importance. Finally the mechanistic questions raised by the products of the acridine oxidation were treated by potential dependent chronocoulometry24, 25 and a mechanistic pathway consistent with these measureL ments was determined.
EXPERIMENTAL
Apparatus
The electrochemical instrumentation was conventional. The triangle wave