2005
DOI: 10.1021/ja0509735
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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-nit… Show more

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Cited by 298 publications
(189 citation statements)
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References 39 publications
(51 reference statements)
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“…In DSC, physical parameters like mass, heat flow, heat capacity and enthalpy [20] are measured with respect to time and temperature. This technique is useful for thermal studies of nitrogen rich energetic molecules.…”
Section: Differential Scanning Calorimetry (Dsc)mentioning
confidence: 99%
“…In DSC, physical parameters like mass, heat flow, heat capacity and enthalpy [20] are measured with respect to time and temperature. This technique is useful for thermal studies of nitrogen rich energetic molecules.…”
Section: Differential Scanning Calorimetry (Dsc)mentioning
confidence: 99%
“…Therefore, five-or six-membered nitrogen-containing heterocycles have been traditional sources of energetic materials. Triazole, tetrazole, and tetrazine derivatives have been investigated extensively as high-energy density materials (HEDMs) both theoretically and experimentally [19][20][21][22][23][24].…”
Section: Introductionmentioning
confidence: 99%
“…[19] Recently, these derivatives have also found numerous new applications ranging from optical waveguides [20] and data storage devices [21] to lightswitchable receptors [22] , and it is likely that new applications and discoveries will be made as the chemistries and structures are further refined. [23] In contrast, very few examples of the synthesis or utilization of (N-phenyl-N'- [1,3,5]triazinyl)diazenes [24,25] , and even less of bis- [1,3,5]triazinyl diazenes [26,27] , can be found in the literature. The main reason is probably the difficulty of synthesizing such compounds by using the traditional diazotization-coupling route, which is employed in the synthesis of various azobenzene compounds.…”
Section: Introductionmentioning
confidence: 99%