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A study of the polarographic reduction of some organic nitro compounds in anhydrous acetic acid

University of British Columbia

Polarographic results for the reduction of a number of aromatic compounds in anhydrous acetic acid were obtained. The compounds studied included: o-, m- and p-nitroanilines and nitro-phenols; o-nitrobenzoic acid; 2,4-dinitro substituted phenol, benzoic acid and toluene; 3,5-dinitro substituted phenol and benzoic acid; 2,4,6-trinitro substituted phenol, benzoic acid and toluene. It has been shown that activating substituents on the benzene nucleus hinder the reduction of nitro groups on the ring, the effect being most pronounced for the o- and p- positions. Hydrogen bonding has been shown to occur to a lesser extent in acetic acid than in aqueous solution. Deactivating groups have been shown to cause nitro substituents to be more easily reduced, the effect decreasing in the order o<m<p. The polarographic reduction of a nitro group has been postulated to proceed with the same mechanism as in aqueous solvents. This reduction has been assumed to be a four or six electron irreversible reaction to the hydroxylamino or amino group repectively. Acetic acid, although limited in the potential range available, has been determined to be a suitable solvent for polarographic studies of organic compounds.

Text

2012-02-08

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http://hdl.handle.net/2429/40555

Chemistry

University of British Columbia

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