The electrochemical reduction mechanism of salicylideneaniline has been investigated by cyclic voltammetry, controlled-potential electrolysis and coulometry. The main reduction product, characterised by HPLC, IR, NMR and X-ray diffractometry, is an anionic dimer, present in two diastereoisomeric forms, together with the conjugate base of the substrate. Kinetic analysis of the voltammetric results has allowed the electrode reaction mechanism to be fully characterised, showing in particular that the rate-determining step is the coupling between two anionic radicals, promoted by intramolecular H-bridging.
Role of proton transfer in the electrochemical reduction mechanism of salicylideneaniline
AHMED ISSE, ABDIRISAK;VIANELLO, ELIO
1997
Abstract
The electrochemical reduction mechanism of salicylideneaniline has been investigated by cyclic voltammetry, controlled-potential electrolysis and coulometry. The main reduction product, characterised by HPLC, IR, NMR and X-ray diffractometry, is an anionic dimer, present in two diastereoisomeric forms, together with the conjugate base of the substrate. Kinetic analysis of the voltammetric results has allowed the electrode reaction mechanism to be fully characterised, showing in particular that the rate-determining step is the coupling between two anionic radicals, promoted by intramolecular H-bridging.
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