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Article Dans Une Revue Chemical Papers Année : 2012

Reaction of aniline with ammonium persulphate and concentrated hydrochloric acid: Experimental and DFT studies

Résumé

In this paper, the reaction of aniline with ammonium persulphate and concentrated HCl was studied. As a result of our experimental studies, 2,4,6-trichlorophenylamine was identified as the main product. This shows that a high concentration of HCl does not favour oxidative polymerisation of phenylamine, even though the ammonium persulphate/HCl system is widely used in polyaniline synthesis. On the basis of the experimental data and density functional theory for reaction path modelling, we proposed a mechanism for oxidative chlorination of aniline. We assumed that this reaction proceeded in three cyclically repeated steps; protonation of aniline, formation of singlet ground state phenylnitrenium cation, and nucleophilic substitution. In order to confirm this mechanism , kinetic, thermochemical, and natural bond orbital population analyses were performed.
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Dates et versions

hal-01773005 , version 1 (09-05-2018)

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Maciej Przybyłek, Jerzy Gaca. Reaction of aniline with ammonium persulphate and concentrated hydrochloric acid: Experimental and DFT studies. Chemical Papers, 2012, 66 (7), pp.699-708. ⟨10.2478/s11696-012-0163-1⟩. ⟨hal-01773005⟩
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