The effects of substitution on the electrochemical reduction of naphthacenetetrone in N,N-Dimethylformamide

✍ Scribed by Chai-Yu Li; Frederic W. Whitehurst

• Publisher: Elsevier Science
• Year: 1982
• Tongue: English
• Weight: 411 KB
• Volume: 27
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(82)85047-0

✦ Synopsis

The polarographic reduction of 5, 6, 11, 12-naphthacenetetrone (NT) and several of its chloro, methyl, and nitro derivatives were investigated . The electrochemical behavior of NT was compared with 6,11-dihydroxy-5,12-naphthacenequinone (DHNQ) previously studied . Like DHNQ, NT exhibits two reduction waves in N, N-dimethylformamide . However, two additional post adsorption waves which were not present in DHNQ reduction were also observed. The first step reduction of NT, representing the formation of the radical anion NT --, has a potential (0.01 V vs sce) much more anodic than that of its DHNQ counterpart (-0.75 V vs see) . The substituent effects of NTs were noted . A linear Hammett relationship similar to that ofthe DHNQ series was also found for the NTs . In both cases, the averaged values of a m and a .. were used as the substituent constants .