Structural, thermochemical and detonation performance of derivatives of 1,2,4,5-tetrazine and 1,4 N-oxide 1,2,4,5-tetrazine as new high-performance and nitrogen-rich energetic materials

Roknabadi, Akbar Gholami; Keshavarz, Mohammad Hossein; Esmailpour, Karim; Zamani, Mehdi

doi:10.1007/s13738-016-0957-0

Cited by 12 publications

(8 citation statements)

References 49 publications

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“…The DFT method of B3LYP combines Becke's threeparameter (B3) 27 functional with the Lee-Yang-Parr (LYP) 28 correlation functional, which has been considered to be capable of accurately predicting the structural parameters and frequencies of many nitro-substituted compounds. [29][30][31] Moreover, the 6-311++G** basis set can generally give satisfactory geometries. 32 All of the optimized molecular structures in this paper belong to local minima on their singlet spin state potential surface and have no imaginary frequency.…”

Section: Theoretical Methodsmentioning

confidence: 99%

Carbon-free energetic materials: computational study on nitro-substituted BN-cage molecules with high heat of detonation and stability

Zeng

Jiao

2018

RSC Adv.

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A new series of high-energy density materials (HEDMs) B 6 N 6 H 6Àn (NO 2 ) n (n ¼ 1-6) are studied at the M06-2X/6-311++G**, uB97XD/6-311++G** and B3LYP/6-311++G** levels. Analysis of the structural changes caused by substituting the NO 2 and the electronic structures, such as electron localization function (ELF), Wiberg bond index (WBI), charge transfer and bond dissociation energies (BDE), provide important insights into the essence of the chemical characteristics and stability. Moreover, the Born-Oppenheimer molecular dynamic (BOMD) simulation is performed to verify their stability, which suggests that only the BN-cage derivatives with one and two nitro groups bonding with boron atoms (NO 2 -1-1 and NO 2 -2-1) can remain stable under ambient conditions. To predict the detonation performance and sensitivity of these two stable BN-cage energetic molecules accurately, the density, gas phase enthalpy of formation, enthalpy of sublimation, detonation performance, impact sensitivity and BDE are calculated systematically. The calculation results show that both NO 2 -1-1 and NO 2 -2-1 have a higher heat of detonation, higher value of h 50 , and larger BDE of trigger bonds than CL-20.

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Section: Theoretical Methodsmentioning

confidence: 99%

Carbon-free energetic materials: computational study on nitro-substituted BN-cage molecules with high heat of detonation and stability

Zeng

Jiao

2018

RSC Adv.

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“…[ 71 ] These approaches were successfully applied for the investigation of the crystal density for a variety of high‐energy materials. [ 4–6,10,12,14,19–25 ]

ρ = ((), \frac{M}{V_{m}})

ρ = α ((), \frac{M}{V_{m}}) + β ((), {italicνσ}_{tot}^{2}) + γ

…”

Section: Theoreticalmentioning

confidence: 99%

“…[ 13 ] Roknabadi et al used DFT calculations to estimate thermochemical and detonation performance of new high‐energy tetrazine derivatives. [ 14 ] Borisov et al predicted the energetic properties of carboranyl tetrazoles based on the DFT studies. [ 15 ] Wang et al used DFT calculations to explore the detonation characters for a series of NO 2 ‐substituted pyrimidine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Performance of NO₂‐rich multifunctionalized C₆₀ derivatives as new high‐energy‐density nanomaterials

Moghadam

Zamani

2020

Int J of Quantum Chemistry

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In this study, density functional theory (DFT) with the aid of B3LYP/6‐311G(d,p) calculations was used to investigate thermochemical and energetic properties for a set of NO2‐rich multifunctionalized C60 derivatives with 2‐nitrophenyl, 4‐nitrophenyl, 2,4‐dinitrophenyl, and up to six 2,4,6‐trinitrophenyl substituents for the first time. The molecular surface properties derived from electrostatic potential analysis were used to calculate enthalpies of sublimation. The gas‐phase enthalpies of formation were estimated using the isodesmic approach. The crystal densities and solid‐phase enthalpies of formation, which are the main factors for predicting detonation performance of high‐energy‐density materials, were calculated. The appropriate theoretical equations were used to predict heats of detonation, detonation velocities, and detonation pressures. It was found that the NO2‐rich multifunctionalized C60 derivatives are compounds with a large density and very high positive heat of formation. The detonation performance of molecules containing several 2,4,6‐trinitrophenyl substituents is comparable to the conventional explosives such as 1,3,5‐trinitrobenzene and 2,4,6‐trinitrotoluene. Therefore, these compounds can be introduced as new high‐energy‐density nanomaterials.

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“…The multiple linear regression method [29] was used to find the optimized model as: give increasing and decreasing functions in the triazolium-based EISs, respectively. For the design of high detonation or combustion performance compounds, it is desirable to choose those materials with high positive heats of formation [3,[5][6][7][8][9][10]30]. Coefficients in Equation 1 show the contributions of the different variables for obtaining a high heat content in triazolium-based EISs.…”

Section: Deriving the New Modelmentioning

confidence: 99%

“…Since energetic derivatives of nitrogen-rich heterocyclic materials have usually more than 50 wt.% nitrogen, they are called high nitrogen content (HNC) materials [4]. Different predictive methods can be used to design high-performance HNC explosives with desirable physicothermal, detonation and combustion properties as well as low sensitivities [3,[5][6][7][8][9][10][11]. Due to the importance of the condensed phase heats of formation of HNCs, several methods, including group additivities and quantitative structure-property relationships (QSPR), have been used in recent years [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Accurate Prediction of the Condensed Phase (Solid or Liquid) Heat of Formation of Triazolium-based Energetic Ionic Salts at 298.15 K

Jafari¹,

Davtalab²,

Keshavarz³

et al. 2018

Cent. Eur. J. Energ. Mater.

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A novel method is introduced for the reliable prediction of the condensed phase (solid or liquid) heat of formation (Δf H θ (c)) of triazolium-based energetic ionic salts (EISs) at 298.15 K. It is based on the influence of some specific elemental compositions of cations and anions as additive parts. Two correcting functions, as non-additive quantities, are also used to adjust the first part. The coefficients of the specific elemental compositions of cations and anions in the new correlation, with a negative sign as well as a negative correcting function in the triazolium-based EISs, can decrease the value of Δf H θ (c) for the corresponding EISs. The reported Δf H θ (c) values of 57 different triazolium-based EISs were used to derive the new model. For 34 triazolium-based EISs, where the outputs of quantum mechanical methods were available, the Root Mean Squared Error (RMSE) of the new model was 156.0 kJ/mol. Meanwhile, the RMSE of complicated quantum mechanical methods is very large, i.e. 298.0 kJ/mol. The high reliability of the new model was also confirmed for a further 5 complex triazolium-based EISs as compared to the results of quantum mechanical calculations.

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Structural, thermochemical and detonation performance of derivatives of 1,2,4,5-tetrazine and 1,4 N-oxide 1,2,4,5-tetrazine as new high-performance and nitrogen-rich energetic materials

Cited by 12 publications

References 49 publications

Carbon-free energetic materials: computational study on nitro-substituted BN-cage molecules with high heat of detonation and stability

Carbon-free energetic materials: computational study on nitro-substituted BN-cage molecules with high heat of detonation and stability

Performance of NO₂‐rich multifunctionalized C₆₀ derivatives as new high‐energy‐density nanomaterials

Accurate Prediction of the Condensed Phase (Solid or Liquid) Heat of Formation of Triazolium-based Energetic Ionic Salts at 298.15 K

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Structural, thermochemical and detonation performance of derivatives of 1,2,4,5-tetrazine and 1,4 N-oxide 1,2,4,5-tetrazine as new high-performance and nitrogen-rich energetic materials

Cited by 12 publications

References 49 publications

Carbon-free energetic materials: computational study on nitro-substituted BN-cage molecules with high heat of detonation and stability

Carbon-free energetic materials: computational study on nitro-substituted BN-cage molecules with high heat of detonation and stability

Performance of NO2‐rich multifunctionalized C60 derivatives as new high‐energy‐density nanomaterials

Accurate Prediction of the Condensed Phase (Solid or Liquid) Heat of Formation of Triazolium-based Energetic Ionic Salts at 298.15 K

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Performance of NO₂‐rich multifunctionalized C₆₀ derivatives as new high‐energy‐density nanomaterials