title: Changed reactivity of the 1-bromo-4-nitrobenzene radical anion in a room temperature ionic liquid.
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, ([C4mPyrr][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.
authors.affiliation: Department of Chemistry, Physical and Theoretical Chemistry Laboratory, Oxford University, Oxford, UK.
authors.forename: Sven
authors.initials: S
authors.lastname: Ernst
authors.forename: Kristopher R
authors.initials: KR
authors.lastname: Ward
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Norman
authors.forename: Christopher
authors.initials: C
authors.lastname: Hardacre
authors.forename: Richard G
authors.initials: RG
authors.lastname: Compton
mesh_terms: D000838:Anions / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry*; D013696:Temperature
chemical_list: C583462:1-bromo-4-nitrobenzene; D000838:Anions; D005609:Free Radicals; D052578:Ionic Liquids; D009578:Nitrobenzenes