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Electrochemical behavior of mutagenic nitro and amino derivatives of carbazole
Author(s) -
Carlier Roger,
Raoult Eugène,
Tallec André,
Andre Vèronique,
Gauduchon Pascal,
Lancelot JeanCharles
Publication year - 1997
Publication title -
electroanalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 128
eISSN - 1521-4109
pISSN - 1040-0397
DOI - 10.1002/elan.1140090118
Subject(s) - carbazole , electrochemistry , chemistry , protonation , nitro , combinatorial chemistry , acetic acid , amino acid , medicinal chemistry , organic chemistry , electrode , biochemistry , ion , alkyl
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 nitrocarazoles 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. The relationships between these electrochemical behaviors and mutagenic properties of the studied compounds are also discussed.