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Title
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Electrochemical reduction of halogenated aromatic compounds at metal cathodes in acetonitrile
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Author
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Abstract
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| A systematic mapping of the catalytic activity combined with mechanistic tendencies for the electrochemical reduction of aromatic halides has been conducted for different cathode materials. The electrochemical reduction of different aromatic bromides has been investigated at several bulk electrodes in CH3CN + 0.1 M TBAP. The aromatic bromides that have been selected, differing in their number of aromatic rings, ring configuration and position of the carbon-halogen bond. The observed catalytic activity is dependent on all of these factors showing that a change in C-X bond strength and stabilisation of the radical anion/radical have different consequences. Glassy Carbon (GC), Ag, Au, Pd, Cu, Ti, Pt, Ni, Zn, Mg, Mn have been used as cathode materials and obviously have a profound effect on electrocatalysis. Transfer coefficients for the dissociative electron transfer indicated that catalysis is not solely reflected by the peak potentials but also by the reaction mechanism. GC has been used as an inert reference system. Silver shows the best catalytic activity, coinciding with literature on other organic halides. Pd, Zn and Ni present instability after a certain amount of cycles. Ti, Pt, Mn and Mg did not seem to be very active for the used compounds. 9-Bromoanthracene was the most reactive of the tested reagents, reacting with all cathode materials and presenting a reversible couple at moderate overpotentials. Electrolysis products have been determined by GC/MS and quantified by HPLC/PDA for GC and Ag cathodes and showed that the corresponding hydrogenated aromatic compound was the only detectable product. |
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Language
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English
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Source (journal)
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Electrochimica acta. - London
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Publication
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London
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2020
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ISSN
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0013-4686
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DOI
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10.1016/J.ELECTACTA.2019.135484
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Volume/pages
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332
(2020)
, 9 p.
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Article Reference
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135484
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ISI
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000506201800023
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Medium
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E-only publicatie
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Full text (Publisher's DOI)
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Full text (open access)
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Full text (publisher's version - intranet only)
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