Products from interaction of aromatic nitrocompounds with argon metastables inside a gas chromatograph

Abstract

The neutral products resulting from the degradation of aromatic nitrocompounds, following interaction with argon metastables (presumably by Penning ionization), have been studied inside a gas chromatographic system. The simplest but typical example, nitrobenzene, yields benzene and phenol. Product ratios sometimes resemble results of mass spectrometry more than they do data obtained by pyrolysis. The ease of elimination of substituents from monohalogenated nitrobenzenes follows the order I > NO2 > Br > Cl. Ratios of the products resulting from loss of NO (rearrangement) versus loss of NO2 have been measured for a variety of compounds. The leaving NO2 group can be replaced by I if the system is doped with iodine vapour. Reduction of the nitro group and ring closures are observed with some of the more complex substrates, similar to results known from discharge chemistry.