AI Article Synopsis
- - The study investigates how tris(4-bromophenyl)amine is oxidized electrochemically with the help of 2,6-lutidine in acetonitrile using voltammetry and spectroscopy.
- - It finds that the oxidation process involves a radical cation that interacts with 2,6-lutidine through a specific electron transfer mechanism, and it provides an estimated equilibrium constant for this reaction.
- - Finally, the research uses electrochemical Electron Spin Resonance (ESR) to analyze the oxidation of phenyl selenoglycoside, determining the resulting products using proton NMR and mass spectrometry, supporting the proposed mechanism with computational simulation results.
Article Abstract
The electrochemical oxidation of tris(4-bromophenyl)amine in the presence of 2,6-lutidine is examined in acetonitrile. Voltammetric and spectroscopic investigations suggest that the electrogenerated triaryl aminium radical cation oxidizes 2,6-lutidine in an EC' mechanism, and an equilibrium constant for this homogeneous electron transfer is estimated. The mediated oxidation of a protected phenyl selenoglycoside by this reaction mixture is studied by the use of electrochemical ESR, employing a tubular flow cell, and signal intensity data is found to be consistent with the proposed mechanism, allowing the determination of kinetic parameters by computational simulation. Products of the mediated glycoside oxidation are determined by proton NMR and mass spectrometry.
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| http://dx.doi.org/10.1021/jp0535137 | DOI Listing |
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