Electrochemical behavior of mutagenic nitro and amino derivatives of carbazole

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