[The role of halogenation in the electro-oxidation of halogenated anilines in acetonitrile as the solvent].
The 4-halogeno-, 2,4-dihalogeno- and 2,4,6-trihalogenoanilines were the model substances of the research described. Acetonitrile being one of the most popular aprotic solvent was used. The halogeno monomers were chloro and bromoanilines. The electrodimerised substrate is stabilised by rejecting halogenide ion and protons. The rejected halogenide ions are oxidisable more easier compared to the substrate therefore the halogene formed substitutes both the substrate, and the dimer as well. The protons formed during the oxidation bind by the strong base monomer primary amine. Because of these not only a simple electrodimerisation will take place, but protonised monomers, higher halogenated monomers, and the corresponding dimer molecules are formed in the solution.
Pusztai
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ELTE Szervetlen és Analitikai Kémiai Tanszék, 1117 Budapest, Pázmány P. sétány 1/A.
Dankházi
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Farsang
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D000097:Acetonitriles; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry / Q000379:methods; D006219:Halogens; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012997:Solvents
D000097:Acetonitriles; D000814:Aniline Compounds; D006219:Halogens; D006846:Hydrocarbons, Halogenated; D012997:Solvents; C032159:acetonitrile