Abstract
The electrochemical reduction of aliphatic t-nitro compounds was studied in anhydrous acetonitrile by polarography and large scale controlled potential electrolysis. The first step of the electrode process involved a one-electron transfer leading to an unstable nitro anion radical which cleaved to nitrite ion and the corresponding free radical. This mechanism was substantiated by controlled potential electrolysis of t-nitrobutane and three α-nitroisobutyric acid derivatives. The differences in polarographic behaviour between t-nitrobutane and α-nitroisobutyric acid derivatives and the results of their electrolysis in the presence of a proton donor were related to the stability of the nitro anion radical and the reducibility of the nitroso derivatives. The predominant factor governing the half-wave potential was the inductive effect of the substituent. An extended Hückel MO calculation was carried out, but the results are unsatisfactory.
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