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The effects of substitution on the eletrochemical reduction of dihydroxynaphtacenequinone in N,N-dimethylformamide

✍ Scribed by Chia-Yu Li; Myron L. Caspar; Donald W. Dixon Jr.


Publisher
Elsevier Science
Year
1980
Tongue
English
Weight
765 KB
Volume
25
Category
Article
ISSN
0013-4686

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✦ Synopsis


Abstrmct -The electrochemical reduction of 6,11-dihydroxy-5,12-naphthacenequinone (DHNQ) in N,Ndimethylformamide was investigated. Under polarographic conditions, DHNQ behaves like a simple aromatic quinone with reduction occurring in two successive one-electron steps followed by protonation in the aprotic system and a single two-electron irreversible step in the protic medium. The substituent inductive effects in several DHNQ derivatives were noted. The electron withdrawing groups, chloro and phenylsulfonyl, enhance the oxidation potentials, and the electron-releasing groups, methyl and methoxy, make the reduction more difficult. The strength of the substituents follows the order: C,H,S02 > Cl r CH, z CH .O. A linear Hammett relationshin exists in this series when the averaged value of umctu and c~,__ are used as substitution constants.


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