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1 Polish Journal of Chemistry

1 1998

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Electrochemical reduction of p-chloronitrobenzene in dipolar aprotic solvents containing carboxylic acids

Wagner-Czauderna E., Orłowska E., Kalinowski M.K.

Polish Journal of Chemistry

1998

Vol. 72, nr 9

2127-2133

The effect of carboxylic acids of different strenght on polarographic behaviour of p-chloronitrobenzene in N, N-dimethylformamide has been investigated. In the presence of each acid a pre-wave appeared at a more positive potential than the original one, which was associated with the cathodic reduction of a hydrogen-bonded adduct, formed between the nitrocompound and the acid molecules in the double layer of the electrode. A linear correlation has been found between delta E-1/2 and pK(DMF/HA) (pK(DMF/HA) refers to the value of the pK-a measured in N, N-dimethylformamide, whereas delta E-1/2=E(pre-wave/1/2) - E(original wave/1/2)). Measurements in a solvent series in the presence of benzoic acid (BA) led to the correlation between delta E-1/2 and pK-BA (the symbol pK-BA denotes the value measured in a given solvent). The slopes of regression lines are discussed in terms of the double layer effect on the basicity of the -NO2 group.