The electrochemical behavior of nitro and amino carbazole derivatives
has been investigated. In aprotic medium, both in reduction and oxidat
ion, the electrochemical process is complicated by ''father-son'' prot
onation reactions. In protic medium, the hydroxylamines resulting from
4-electron reduction of nitrocarbazoles are unstable in very acidic m
edium, but relatively stable in acetic or ammoniacal buffer, except fo
r 3-hydroxyl-aminocarbazole; reduction of amino-nitrocarbazoles leads
to unstable hydroxylamines. Oxidation of aminocarbazoles is a 2-electr
on process, the 2-amino compounds being more difficult to oxidize than
the 3-amino derivatives. Thr relationships between these electrochemi
cal behaviors and mutagenic properties of the studied compounds are al
so discussed.