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Reaction of aniline with ammonium persulphate and concentrated hydrochloric acid: Experimental and DFT studies
Abstract
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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- Category:
- Magazine publication
- Type:
- Magazine publication
- Published in:
-
CHEMICAL PAPERS
no. 66,
edition 7,
pages 699 - 708,
ISSN: 0366-6352 - Publication year:
- 2012
- DOI:
- Digital Object Identifier (open in new tab) 10.2478/s11696-012-0163-1
- Verified by:
- No verification
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