The preparation of, and electrochemical studies on, some substituted aryl dithiadiazolylium salts and dithiadiazolyl radicals |
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Authors: | Christine M Aherne Arthur J Banister Thomas G Hibbert Anthony W Luke Jeremy M Rawson |
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Institution: | a Department of Chemistry, Durham University, South Road, Durham DH1 3LE, U.K. b Department of Chemistry, The University of Cambridge, Lensfield, Cambridge CB2 1EW, U.K. |
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Abstract: | A series of aryl-substituted 1,2,3,5-dithiadiazolylium cations (I) and 1,3,2,4-dithiadiazolylium cations (II) were prepared as their hexafluoroarsenate(V) salts using standard methods. Electrochemical studies on I and II showed reversible one-electron reductions. The half-wave reduction potentials for a series of meta-substituted derivatives of both I and II exhibited a linear free energy relationship with the Hammett parameter, σm. The small value of the reaction constant, , for both meta and para-derivatives indicates that electronic effects are small and in the case of the ortho-derivatives of II, steric effects dominate the redox process. Reduction of the 1,2,3,5-dithiadiazolylium cations, as their chloride salts, yielded the corresponding dithiadiazolyl radicals (III). |
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Keywords: | sulfur nitrogen dithiadiazolylium dithiadiazolyl electrochemistry |
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