Substituted nitrobenzenes were among the first organic compounds to be investigated using the polarographic technique. The early work was performed by the Japanese, Shikata and his co-workers, and from this work Shikata and Tachi3 formulated the "electronegativity rule of reduction potentials," i. e., that organic compounds are more easily reduced as more electronegative groups are substituted in the same molecule.These investigators measured the reduction potentials by the tangent method us. the normal calomel electrode. This method of measurement deviates from present practice. I t was felt desirable to extend their investigations of substituted nitrobenzenes and to determine the relative effect of the position of the substituent upon the reduction process.The ortho-, meta-and para-isomers of nitrobenzoic acid, dinitrobenzene, nitrochlorobenzene, and nitrotoluene were selected for study. The reduction of these compounds a t the dropping mercury cathode from carefully buffered solutions over the PH range 2 to 14 was investigated to determine the nature of the reduction process and the effect of the position of the substituent groups upon the half-wave reduction potential. ExperimentalAll of the compounds investigated were obtained from Eastman Kodak Company and were further purified before use. Water solutions of 0.002 M concentration of oand m-nitrobenzoic acids and of 0.001 M concentration of
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