Changed reactivity of the 1-bromo-4-nitrobenzene radical anion in a room temperature ionic liquid

Sven Ernst, Kristopher R. Ward, Sarah E. Norman, Christopher Hardacre, Richard G. Compton*

*Corresponding author for this work

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Radical anions of 1-bromo-4-nitrobenzene (p-BrC6H4NO2) are shown to be reactive in the room temperature ionic liquid N-butyl-N-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, ([C(4)mPyrr][NTf2]), by means of voltammetric measurements. In particular, they are shown to react via a DISP type mechanism such that the electrolysis of p-BrC6H4NO2 occurs consuming between one and two electrons per reactant molecule, leading to the formation of the nitrobenzene radical anion and bromide ions. This behaviour is a stark contrast to that in conventional non-aqueous solvents such as acetonitrile, dimethyl sulfoxide or N,N-dimethylformamide, which suggests that the ionic solvent promotes the reactivity of the radical anion, probably via stabilisation of the charged products.

Original languageEnglish
Pages (from-to)6382-6389
Journal Physical Chemistry Chemical Physics
Volume15
Issue number17
Early online date15 Mar 2013
DOIs
Publication statusPublished - 07 May 2013

Keywords

  • HALONITROBENZENES
  • SOLVENTS
  • MOLTEN-SALTS
  • ELECTRON-TRANSFER
  • VITREOUS CARBON
  • ELECTROCHEMICAL REDUCTION
  • VOLTAMMETRY
  • PHOTOELECTROCHEMICAL REDUCTION
  • BEHAVIOR
  • NITROBENZENE

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