Trinitrobenzyl anion

The introduction of substituents can be achieved through nucleophilic substitution of nitro groups in TNT or its derivatives under the action of the corresponding nucleophiles. Yet, it is known [3,4] that, in the interaction of TNT with bases, instead of substitution of nitro groups, the formation of stable anion a-complexes is observed and a proton is eliminated from the methyl group yielding the 2,4,6-trinitrobenzyl anion with subsequent transformations of this anion taking place (Scheme 4.2). 

This colored complex was used to develop colorimetric tests for many nitro aromatic compounds. Whether the Meisenheimer complex or 2,4,6-trinitrobenzyl anion (TNT ) resulting from proton abstraction reacted further with TNT (or with excess hydroxide) to form larger species is still not clear, but alkaline hydrolysis of TNT in aqueous media led to large molecular weight compounds (60% > 30 kDa [28] 40% > 1 kDa [30]). 

All types of nitro compds react easily with bases, forming diverse types of products (Ref 36) In the case of TNT, 2,4,6-trinitrobenzyl anion (I) is formed initially and rapidly. It is a highly reactive species thought to be intermediate in the many reactions of TNT conducted under basic conditions discussed above (Refs 32 61). The anion is formed without side reactions by the action of 1,1, 3,3 -tetramethylguanidine in dimethylformamide solvent (Ref 106). Based on... 

---