Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound

Article abstract of DOI:10.1021/ja0509735

The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NδH_f), experimentally determined using an additive method, is shown to be the highest positive NδH_f compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C-N compounds, for example, 2,4,6-triazido-1,3,5- triazine; 4,4′,6,6′-tetra(azido)hydrazo-1,3,5-triazine; 4,4′,6,6′-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3, 4,6,7,9,9b-heptaazaphenalene (heptazine).