Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound
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- 20 August 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (36), 12537-12543
- https://doi.org/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 (NΔHf), experimentally determined using an additive method, is shown to be the highest positive NΔHf 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).Keywords
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