Insensitive Nitrogen-Rich Materials Incorporating the Nitroguanidyl Functionality

A new class of nitroguanidyl-functionalized nitrogen-rich materials derived from 1,3,5-triazine and 1,2,4,5-tetrazine was synthesized through reactions between N-nitroso-N-alkylguanidines and the hydrazine derivatives of 1,3,5-triazine or 1,2,4,5-tetrazine. These compounds were fully characterized using multinuclear NMR and IR spectroscopies, elemental analysis, and differential scanning calorimetry (DSC). The heats of formation for all compounds were calculated with Gaussian 03 and then combined with experimental densities to determine the detonation pressures (P) and velocities (D-v) of the energetic materials. Interestingly, some of the compounds exhibit an energetic performance (P and D-v) comparable to that of RDX, thus holding promise for application as energetic materials.