Electrochemical behaviour of heterocyclic amine derivatives in media of controlled proton availability: Part I. Reduction mechanism and electron spin resonance study of 2-phenyl 4-substituted quinolines in DMF |
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Authors: | R. Andruzzi A. Trazza L. Greci L. Marchetti |
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Affiliation: | 1. Istituto di Chimica della Facoltà di Ingegneria dell''Università, Via del Castro Laurenziano, 7-00161 Rome, Italy;2. Centro di Studio per la Elettrochimica e la Chimica Fisica delle Interfasi del C.N.R., Via del Castro Laurenziano, 7-00161 Rome, Italy |
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Abstract: | The electroreduction of some 4-substituted 2-phenylquinolines in dimethylformamide solutions was studied by dc and ac phase selective polarography, cyclic voltammetry, controlled-potential coulometry, ESR and UV spectrometry, in the presence and absence of protonating agents.In a protic medium 2-phenylquinolines are reduced via a bielectronic polarographic step to the corresponding 1,4-dihydroquinolines. In an aprotic medium two well-defined reduction steps are observed. The first is a reversible one-electron transfer producing a stable anion radical characterized by ESR spectroscopy. The second is an irreversible one-electron transfer producing the di-anion. A multistep scheme for the reduction process consistent with the experimental results is proposed. |
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Keywords: | To whom correspondence should be addressed. |
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