Decomposition Mechanism of 5,5′-Bis(tetrazole)-1,1′-diolate(TKX-50) Anion Initiated by Intramolecular Oxygen Transfer

Zhao, Siwei; Zhao, Ying; Xiao, Xing; Ju, Xue‐Hai

doi:10.1007/s40242-019-8332-1

Cited by 8 publications

(3 citation statements)

References 17 publications

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“…A few studies have only concomitantly mentioned the variation of aromaticity in studying other problems but no further step. [107,108] Owing to the close relationship between aromaticity and stability, we employ two complexes as shown in Figure 1, where complex I is the most common molecular structure corresponding to the crystal structure of TKX-50 [109][110][111] and complex II is the most stable one in ten possible complexes obtained by Talawar et al [112] through complex searching at ωb97xd/6-311 + + g-(3df,3pd) level of theory in the gas phase, to deep study the aromaticity of TKX-50 molecules and first found that the aromaticity of TKX-50 is constituted by π-aromaticity and a comparable amount of σ-aromaticity. This provides a new and deeper perspective on the aromaticity of TKX-50 and its related properties as a promising energetic material such as stability, impact sensitivity, and heat decomposition.…”

Section: Introductionmentioning

confidence: 99%

“…However, the aromaticity of the bi‐tetrazole ring in TKX‐50 has not attracted much attention from researchers. A few studies have only concomitantly mentioned the variation of aromaticity in studying other problems but no further step [107,108] . Owing to the close relationship between aromaticity and stability, we employ two complexes as shown in Figure 1, where complex I is the most common molecular structure corresponding to the crystal structure of TKX‐50 [109–111] and complex II is the most stable one in ten possible complexes obtained by Talawar et al [112] .…”

Section: Introductionmentioning

confidence: 99%

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The σ+π dual aromaticity of typical bi‐tetrazole ring molecule TKX‐50

Yang,

Dong,

et al. 2024

ChemPhysChem

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Two complexes of dihydroxylammonium 5,5´‐bistetrazole‐1,1´‐diolate (TKX‐50) were employed to evaluate the aromaticity of their tetrazole rings via deep analysis such as the electronic structure, the ZZ component of the natural chemical shielding tensor (NICSZZ) and component orbitals, localized orbital locator purely contributed by σ‐orbitals (LOL‐σ) and localized orbital locator purely contributed by π‐orbitals (LOL‐π), the anisotropy of the induced current density(AICD) and the ZZ component of iso‐chemical shielding surface(ICSSZZ)of these tetrazole rings thereof. The conclusion shows: that all tetrazole rings and bi‐tetrazole rings in complexes have strong σ and a comparable strength π double aromaticity; all these magnetic shields almost symmetrically increase from the central axis to the tetrazole ring atoms; tetrazole rings in complex II show a little stronger dual aromaticity than that in complex I mainly due to the different orientation of the fragment 2 encompassing two hydroxylamine groups resulting in different effects on the contributions of σ orbitals and π orbitals to total aromaticity of tetrazole rings thereof; the difference in aromaticity is fundamentally caused by the atoms O with stronger electron‐withdrawing than atom N in fragment 2 interact with bi‐tetrazole ring through O in complex I but through N in complex II.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The σ+π dual aromaticity of typical bi‐tetrazole ring molecule TKX‐50

Yang,

Dong,

et al. 2024

ChemPhysChem

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“…Due to the excellent comprehensive performance of TKX-50, it has attracted extensive attention from numerous researchers, despite extensive research on thermal decomposition mechanisms, − recrystallization, − synthesis, , high pressure stability. − Most of the experimental studies on thermal decomposition of TKX-50 were based on differential scanning calorimetry, thermogravimetry, and other instruments, as its dosage was too small (0.3–1.0 mg) to detect its heat signal effectively and accurately. Lack of experimental studies exist on the effects of relatively large mass effects on the thermal decomposition of TKX-50, and the thermal decomposition of TKX-50 had a complex reaction mechanism.…”

Section: Introductionmentioning

confidence: 99%

Thermal Decomposition Characteristics and Thermal Safety of Dihydroxylammonium 5,5′-Bistetrazole-1,1′-diolate Based on Microcalorimetric Experiment and Decoupling Method

Tan

Cao

et al. 2020

J. Phys. Chem. C

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A microcalorimeter (C600) was used to conduct dynamic heating experiments on dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50), and the results were compared with those of differential scanning calorimetry (DSC). The effect of mass scale on the thermal decomposition characteristics of TKX-50 was also analyzed. The thermal decomposition curves were decoupled by mathematical method, and the kinetic parameters of each step were obtained. The thermal decomposition characteristics of TKX-50 were further analyzed by thermal history and isothermal experiment, and the thermal safety parameters were calculated by thermal analysis software (AKTS). The decomposition temperature and decomposition enthalpy of TKX-50 in the microcalorimetric experiment were higher than the corresponding parameters in the DSC experiment, and the apparent activation energy was lower than the one in the DSC experiment. When the times to maximum rate under adiabatic conditions were 2.0, 4.0, 8.0, and 24.0 h, the corresponding temperatures were 198.5, 189.6, 181.0, and 168.0 °C, respectively. After decoupling, the range of exothermic peak temperature and decomposition enthalpy of the first and second stages of TKX-50 were 226.9−245.3 and 276.3−295.7 °C and 1300.7 and 727.7 J g −1 , respectively, and the apparent activation energy of the second stage was higher than that of the first stage. The thermal history reduced the decomposition temperature and the apparent activation energy of TKX-50, the safety was reduced, and this had a great influence on the thermal decomposition kinetics of TKX-50. Thermal history and isothermal experiment showed that the first stage decomposition reaction of TKX-50 has autocatalytic properties. Therefore, it should be prevented from being placed in an adiabatic environment, and it is necessary to avoid the storage of a large mass of TKX-50 and keep the heat source off the storage location in the process of industrial production and storage, so as to prevent the formation of adiabatic environments and thermal history in the interior and further reduce the risk of explosion in TKX-50.

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The Chemical Micromechanism of Energetic Material Initiation

Zeman¹

2023

Nano and Micro‐Scale Energetic Materials

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Decomposition Mechanism of 5,5′-Bis(tetrazole)-1,1′-diolate(TKX-50) Anion Initiated by Intramolecular Oxygen Transfer

Cited by 8 publications

References 17 publications

The σ+π dual aromaticity of typical bi‐tetrazole ring molecule TKX‐50

The σ+π dual aromaticity of typical bi‐tetrazole ring molecule TKX‐50

Thermal Decomposition Characteristics and Thermal Safety of Dihydroxylammonium 5,5′-Bistetrazole-1,1′-diolate Based on Microcalorimetric Experiment and Decoupling Method

The Chemical Micromechanism of Energetic Material Initiation

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