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

J Am Chem Soc. 2005 Sep 14;127(36):12537-43. doi: 10.1021/ja0509735.

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides* / chemical synthesis
  • Azides* / chemistry
  • Crystallography, X-Ray
  • Heterocyclic Compounds* / chemical synthesis
  • Heterocyclic Compounds* / chemistry
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Models, Molecular
  • Molecular Structure
  • Nitrogen / chemistry*
  • Thermodynamics*
  • Triazines

Substances

  • Azides
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 3-Ring
  • Triazines
  • Nitrogen
  • heptazine