title: Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound.
abstract: 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 (NDeltaHf), experimentally determined using an additive method, is shown to be the highest positive NDeltaHf 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).
authors.affiliation: Dynamic Experimentation Division, DX-2: Materials Dynamics, MS C920, Los Alamos National Laboratory, Los Alamos, New Mexico 87545, USA. huynh@lanl.gov
authors.forename: My Hang V
authors.initials: MH
authors.lastname: Huynh
authors.forename: Michael A
authors.initials: MA
authors.lastname: Hiskey
authors.forename: David E
authors.initials: DE
authors.lastname: Chavez
authors.forename: Darren L
authors.initials: DL
authors.lastname: Naud
authors.forename: Richard D
authors.initials: RD
authors.lastname: Gilardi
mesh_terms: D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013816:Thermodynamics; D014227:Triazines
chemical_list: D001386:Azides; D006571:Heterocyclic Compounds; D006575:Heterocyclic Compounds, 3-Ring; D014227:Triazines; D009584:Nitrogen; C507296:heptazine