Synthesis and characterization of high energy compounds. I. <i>Trans</i>‐1,4,5,8‐tetranitro‐1,4,5,8‐tetraazadecalin (TNAD)

Wilier, Rodney

doi:10.1002/prep.830080302

Cited by 35 publications

(15 citation statements)

References 15 publications

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“…For comparisons, the experimental detonation performance of HMX, bicycle-HMX, and TNAD is also tabulated in Table together with another known explosive RDX. The calculated detonation velocities and pressures agree well with the available experimental data, − with the relative errors +1.43% and −1.10% for HMX (A1), +0.65% and −8.57% for bicycle-HMX (B11), +2.87% and +5.90% for TNAD (C11), and +1.37% and +2.35% for RDX, respectively. This reflects that our predictions for the title compounds are reliable and further confirms the reliability of the calculation method used for these molecular systems.…”

Section: Resultssupporting

confidence: 81%

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Theoretical Studies on the Heats of Formation, Detonation Properties, and Pyrolysis Mechanisms of Energetic Cyclic Nitramines

Wang

et al. 2011

J. Phys. Chem. A

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Density functional theory calculations were performed to find comprehensive relationships between the structures and performance of a series of highly energetic cyclic nitramines. The isodesmic reaction method was employed to estimate the heat of formation. The detonation properties were evaluated by using the Kamlet-Jacobs equations based on the theoretical densities and HOFs. Results indicate the N-NO(2) group and aza N atom are effective substituents for enhancing the detonation performance. All cyclic nitramines except C11 and C21 exhibit better detonation performance than HMX. The decomposition mechanism and thermal stability of these cyclic nitramines were analyzed via the bond dissociation energies. For most of these nitramines, the homolysis of N-NO(2) is the initial step in the thermolysis, and the species with the bridged N-N bond are more sensitive than others. Considering the detonation performance and thermal stability, twelve derivatives may be the promising candidates of high energy density materials (HEDMs). The results of this study may provide basic information for the further study of this kind of compounds and molecular design of novel HEDMs.

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Section: Resultssupporting

confidence: 81%

“… a Data in parentheses are the experimental values taken from refs − . b For the explosive C a H b O c N d : OB (%) = 1600 × ( c – 2 a – b /2)/ M w , where M w is the molecular weight. …”

Section: Resultsmentioning

confidence: 99%

Theoretical Studies on the Heats of Formation, Detonation Properties, and Pyrolysis Mechanisms of Energetic Cyclic Nitramines

Wang

et al. 2011

J. Phys. Chem. A

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“…[38][39][40][41] Many research groups [42][43][44][45] over the past decades reported energetic materials rich in nitro groups. Selected examples of some familiar oxygen-rich and nitrogen rich explosives such as 1,3,5-trinitrotriazacyclohexane (RDX), [46] 1,3,5,7-tetranitrotetraazacyclooctane (HMX), [47] hexanitrobenzene (HNB), [48] trinitrotoluene (TNT), [49] 4,10-dinitro-4,10-diaza-2,6,8,12-tetraoxaisowurtzitane (TEX), [18,50] trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin (TNAD), [51] penta-erythritol tetranitrate (PETN), [52] hexanitrostilbene (HNS), [53] tetraazidomethane (TAM), [54] 2,2,4,4,6,6-hexanitroadamantane (HNA), [55] 4,4'-Azobis [1,2,4-triazole] (ABTr), [56] along with promising candidates for insensitive munitions (IM) such as 1,1-diamino-2,2-dinitroethylene (FOX-7), [57] 5-nitro-1,2,4triazole-3-one (NTO), [58] and triaminotrinitro benzene (TATB), [59] have been reported in literature.…”

Section: Introductionmentioning

confidence: 99%

Pentacycloundecane (PCUD)‐Based Cage Frameworks as Potential Energetic Materials: Syntheses and Characterization

et al. 2020

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A new variety of cage frameworks containing pentacycloundecane (PCUD) were synthesized. These compounds contain azide and triazole units. Four new cage frameworks were designed and constructed starting from easily accessible starting materials such as 2,3-dimethylhydroquinone, 1,4-dimethoxybenzene, and dicyclopentadiene using [2 + 2] photocycloaddition as the key step. The structures of these symmetrical cage bis-azide and cage bistriazole compounds have been confirmed by single-crystal X-ray diffraction studies. DFT analysis at different levels of theory were used to optimize the geometries and compute the heats of formation of the title compounds. Their propulsive and explosive properties were also calculated using suitable computational methods. The thermodynamic stability of the title compounds was theoretically analysed based on their bond dissociation energies. The thermal stability was evaluated by TGA-coupled FTIR analysis.

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“…27 The strength of bonding is fundamental to understanding the chemical process, which could be evaluated from the BDE. 21,22 Originally, it is defined as the enthalpy change at 298 K and 1.01×10 5 Pa for the chemical bond dissociation in a molecule A-B as follows:…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4] Among them, the explosive trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin (TNAD, Figure 1) was characterized as a promising high energy density material (HEDM) with superior shock sensitivity and thermal stability. 5 It was reported to melt in 232-234 ℃ and decompose only above 220 ℃ according to the thermogravimetry (TG) and differential thermal analysis (DTA). 6 The measured impact sensitivity h 50% (in terms of the height from which a falling 2.5 kg weight will cause detonation 50% of the time) is 35 cm, comparable to the values of 25-28 cm for RDX (1,3,5-trinitro-1,3,5-triazocyclohexane) and 18-26 cm for HMX (1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane) that are among the most effective and widely-used explosives and monopropellants.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Studies on Thermolysis Mechanism and Stability of trans‐1,4,5,8‐Tetranitro‐1,4,5,8‐tetraazadecalin Isomers

Qiu

Gong

Xiao³

2008

Chin. J. Chem.

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A systematic study on the thermolysis mechanism and stability of a series of energetic cyclic nitramines, trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin isomers, was performed by density functional theory (DFT) and semiempirical molecular orbital (MO) calculations. Bond dissociation energies (BDE) and activation energies (E a ) of the thermolysis processes were computed at the B3LYP/6-31G** and PM3 levels, respectively. The effect of nitroamino groups on the thermal stability and pyrolysis mechanism of the title compounds was evaluated by the BDE and E a . The correlations among BDE, E a , bond overlap populations, energies of the frontier orbitals, and energy gaps were examined in detail. The results indicate that thermal stabilities and decomposition mechanisms of the title compounds derived from the BDE, E a and static electronic parameters are basically consistent. Homolysis of the N-NO 2 bond is the initial step in the thermolysis of the title compounds, the meta-isomers are more stable than the para-isomers, and the ortho-isomers are the most sensitive.

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Synthesis and characterization of high energy compounds. I. Trans‐1,4,5,8‐tetranitro‐1,4,5,8‐tetraazadecalin (TNAD)

Cited by 35 publications

References 15 publications

Theoretical Studies on the Heats of Formation, Detonation Properties, and Pyrolysis Mechanisms of Energetic Cyclic Nitramines

Theoretical Studies on the Heats of Formation, Detonation Properties, and Pyrolysis Mechanisms of Energetic Cyclic Nitramines

Pentacycloundecane (PCUD)‐Based Cage Frameworks as Potential Energetic Materials: Syntheses and Characterization

Theoretical Studies on Thermolysis Mechanism and Stability of trans‐1,4,5,8‐Tetranitro‐1,4,5,8‐tetraazadecalin Isomers

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