Voltammetric Studies on Some Thiadiazoles and Their Derivatives
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The redox characteristics of 2-arylaldehydehydrazono-3-phenyl-5-substituted-2,3-dihydro- 1,3,4-thiadiazoles (1a-h) have been investigated in nonaqueous solvents such as 1,2-dichloroethane (DCE), dichloromethane (DCM), acetonitrile (AN), Tetrahydrofuran (THF), and dimethylsulfoxide (DMSO) at platinum electrode. Through controlled potential electrolysis, the oxidation and reduction products of the investigated compounds had been separated and indentified. The redox mechanism had been suggested and proved. It had been found that all the investigated compounds were oxidized in two irreversible one-electron processes following the well-known pattern of The EC-mechanism; the first electron loss gives the corresponding cation- radical which is followed by proton removal from the ortho-position in the N-phenyl ring forming the radical. The obtained radical undergoes a second electron uptake from the nitrogen in the N = C group forming the unstable intermediate (di-radical cation) which undergoes ring closure forming the corresponding cation. The formed cation was stabilized in solution through its combination with a perchlorate anion from the medium. On the other hand, these compounds are reduced in a single two-electron process or in a successive two one-electron processes following the well known pattern of the EEC-mechanism according to the nature of the substituent; the first one gives the anion-radical followed by a second electron reduction to give the dianion which is basic enough to abstract protons from the media to saturate the (C = O) bond.
Abstract
The redox characteristics of 2-arylaldehydehydrazono-3-phenyl-5-substituted-2,3-dihydro- 1,3,4-thiadiazoles (1a-h) have been investigated in nonaqueous solvents such as 1,2-dichloroethane (DCE), dichloromethane (DCM), acetonitrile (AN), Tetrahydrofuran (THF), and dimethylsulfoxide (DMSO) at platinum electrode. Through controlled potential electrolysis, the oxidation and reduction products of the investigated compounds had been separated and indentified. The redox mechanism had been suggested and proved. It had been found that all the investigated compounds were oxidized in two irreversible one-electron processes following the well-known pattern of The EC-mechanism; the first electron loss gives the corresponding cation- radical which is followed by proton removal from the ortho-position in the N-phenyl ring forming the radical. The obtained radical undergoes a second electron uptake from the nitrogen in the N = C group forming the unstable intermediate (di-radical cation) which undergoes ring closure forming the corresponding cation. The formed cation was stabilized in solution through its combination with a perchlorate anion from the medium. On the other hand, these compounds are reduced in a single two-electron process or in a successive two one-electron processes following the well known pattern of the EEC-mechanism according to the nature of the substituent; the first one gives the anion-radical followed by a second electron reduction to give the dianion which is basic enough to abstract protons from the media to saturate the (C = O) bond.
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