ISSN:
1040-0397
Keywords:
Nitroimidazoles
;
Reduction
;
Polarography
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1, 2-Dialkyl-4-nitroimidazoles are reduced between pH 0 and 13 in a four-electron wave. The resulting arylhydroxylamine is stable and in acidic media reduced further to the amine. 1,2-Dialkyl-5-nitroimidazoles and 2-alkyl-4(5)-nitroimidazoles are reduced in alkaline media with the number of electrons approaching six. The hydroxylamine derivative formed in these reductions can be dehydrated and yields an easily reducible, quinone-like ketimine. The rate of the dehydration governs the heights of the first step and is base catalyzed. The sequence of electron and proton transfers for 2- alkylsubstituted nitroimidazoles is the same as that observed for corresponding desalkyl compounds.1-Alkyl-4-amino-5-nitroimidazoles, as well as 1-alkyl-4-nitro-5-aminoimidazoles, are reduced in a single wave, the height of which approaches that of a six-electron process. The dehydration of the hydroxylamino derivative is favored, probably due to an internal base catalysis. The shifts of half-wave potentials with pH differ principally from those of all other nitroimidazoles and indicate the predominant role of the amino group in the proton transfer.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/elan.1140040909
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