Issue 17, 2013

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.

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

Article information

Article type
Paper
Submitted
06 Mar 2013
Accepted
14 Mar 2013
First published
15 Mar 2013

Phys. Chem. Chem. Phys., 2013,15, 6382-6389

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

S. Ernst, K. R. Ward, S. E. Norman, C. Hardacre and R. G. Compton, Phys. Chem. Chem. Phys., 2013, 15, 6382 DOI: 10.1039/C3CP51004B

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