Figure 1 - full size

 

Figure 1.
FIG. 1. Resonance forms of TNT. Panel A, structure of TNT as the resonance hybrid of several canonical forms, illustrating the enhancement in the electrophilicity of C3 and C5, the site of hydride ion addition. Panel B, reduction of TNT by PETN reductase to form the Meisenheimer-hydride complex.

The above figure is reprinted by permission from the ASBMB: J Biol Chem (2004, 279, 30563-30572) copyright 2004.