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Polarographic and electrochemical studies of some aromatic and heterocyclic nitro compounds, part II: Polarographic and voltammetric reduction of some nitramines, pyrazolium, and imidazolium nitro derivatives
Author(s) -
Dumanović D.,
Jovanović J.,
Sužnjević D.,
Erceg M.,
Zuman P.
Publication year - 1992
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.1140040809
Subject(s) - chemistry , hydroxylamine , nitro , polarography , ring (chemistry) , electrochemistry , medicinal chemistry , hydrazine (antidepressant) , nitrous acid , inorganic chemistry , organic chemistry , electrode , alkyl , chromatography
Reduction of 1‐nitropyrazole (I) results in acidic media in a cleavage of the NN bond and formation of nitrous acid which is further reduced at more negative potentials. At pH > 4 a competitive reduction of the nitramine to nitrosamine occurs. Four‐electron reduction of nitro derivatives of pyrazolium (II) and (III) and imidazolium (IV) and (V) salts results in a formation of a hydroxylamine derivative. The reduction follows the scheme: H+, e, e, H+, 2e, 2H+. In the reduction product the azolium ring is reduced at more negative potentials. Whereas the effect of pyrazolium and imidazolium rings on the reducibility of the nitro group is comparable, the interaction between the nitro group and the azolium ring markedly depends on the position of the nitro group on the ring.