Electrochemical reduction of N-aryl- and N-arylsulphonylbenzoquinonemonoimines in acetonitrile—I. Electroreduction mechanism and effects of proton donors on electrochemical process

✍ Scribed by V. Glezer; B. Turovska; J. Stradins; J. Freimanis

• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 851 KB
• Volume: 35
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(90)87102-8

✦ Synopsis

Electrochemical reduction of 1,6benzoquinonemonoimine

derivatives have been studied in acetonitrile. As a rule reduction of monoimines proceeds in two steps, the lirst of them results in the formation of an anion-radical. Introduction of sulpho-group between the quinoneimine and aryl moieties leads to a considerable increase of electronacceptor properties of compounds under investigation and to decrease of their reduction products nucleophilicity.

In the case of quinonemonoiminium perchlorates electrochemical reduction proceeds also in two one-electron steps. The binding of the nitrogen lone pair electrons and a change in the total charge of the system during the protonation of the quinoneimine molecules leads to an anodic shift of the lirst reduction wave about 1.2 V. The free radical forming during the first electron transfer seems to be reduced by more positive potentials as molecules of initial quinoneimines.