Influence of Methyl Substituent Position on Redox Properties of Nitroaromatics Related to 2,4,6-Trinitrotoluene

The environmental remediation of military installation sites is very important due to frequently large presence of carcinogenic derivatives of explosives in the ground and in ground waters. These nitroaromatic explosives and their derivatives are assessed by sensing devices. It is highly important to have insight on the reasons affecting the reduction potentials of these compounds. The redox properties of mono-, di- and tri-nitroaromatic compounds are studied with cyclic voltammetry at a glassy carbon electrode for comparison. We show that the presence of a methyl group in the aromatic system leads into more negative reduction potentials. The ease of nitro group reduction vary from meta>para>ortho positions relative to a methyl group. The redox properties were also studied at various pH ranging from 2 to 10. Acidic environments facilitated the reduction processes at lower potentials. These findings will have a profound influence upon understanding the processes during reductive decontaminations of the polluted sites as well as for construction of highly sensitive sensors for their determination.