Birch reduction of chlorobenzene in gas-phase hydrated electrons

Reactions of gas-phase hydrated electrons (H2O)n−, n = 30–65, with chlorobenzene are investigated by Fourier transform ion cyclotron resonance mass spectrometry. The clusters lose water molecules via collision and black-body radiation induced dissociation. In addition, chemical reactions with chlorobenzene lead to formation of Cl−(H2O)n and OH−(H2O)n. While the former product is well-known from pulsed radiolysis studies in the bulk, the latter is observed for the first time in gas-phase clusters. It is indicative of a Birch reduction of the aromatic ring, leading to formation of a chloro-cyclohexadienyl radical C6H6Cl.