Homogenous Gas-Phase Formation and Destruction of Anthranil from o-Nitrotoluene Decomposition

Article abstract of DOI:10.1021/ja00220a006

Dilute quantities of o-nitrotoluene and anthranil have been pyrolyzed in comparative rate single pulse shock tube experiments.Rather than C-NO2 bond cleavage and NO2 isomerization found as major channels in p-nitrotoluene decomposition, we demonstrate that the important pathway for pyrolysis involves the formation of anthranil with the following overall rate expression: k(o-nitrotoluene -> anthranil) = 1.2 x 10¹³ exp(-26020/T)/s.The anthranil that is formed is very unstable under our conditions; the rate expression for disappearence has been found to be the following: k(anthranil)_d = 3.7 x 10¹⁵ exp(-25800/T)/s.Arguments are presented that suggest that the first rate expression is representative of a retroene reaction and the second expression is for the breaking of the N-O bond in anthranil.These conclusions emphasize the difference in results from shock tube and laser pyrolysis experiments.Their implications on the initiation reactions in the decomposition of nitroaromatic explosives are discussed.