Synthesis and chemistry of some furazano- and furoxano[3,4-b]piperazines

Willer, Rodney L.; Moore, Donald W.

doi:10.1021/jo00225a029

Cited by 65 publications

(54 citation statements)

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“…(1) and (2) is defined as follows: D, detonation velocity (km•s -1 ); P, detonation pressure (GPa); ρ, density of a compound (g•cm -3 ); N, moles of gaseous detonation products per gram of explosive; M , average molecular weight of gaseous products; Q, chemical energy of detonation (kJ•g -1 ). Here, the parameters N, M , and Q were calculated according to the chemical composition of each explosive as listed in Table 1.…”

Section: Methodsmentioning

confidence: 99%

“…In recent years, syntheses of heterocyclic compounds have attracted a great amount of interest since heterocycles generally have higher heat of formation, density, and oxygen balance than their carbocyclic analogues, in which furazan and furoxan-fused cyclic nitramines have raised popular interest due to their improved density, energy, and detonation performances than the simpler nitramines. [1][2][3][4][5][6][7] Furthermore, compounds containing the furazan or furoxan rings decompose exothermically and have, therefore, potential interest in the explosive and solid rocket-propellant fields. It has been stated that replacing the nitro group by the furoxan ring in the explosives will achieve an increase in their density, detonation velocity, and stability.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Study on the High Energy Density Compound Hexanitrohexaazatricyclotetradecanedifuroxan

Qiu¹,

Xiao²,

Zhu³

et al. 2006

Chin. J. Chem.

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Density functional theory (DFT) has been employed to study the molecular geometries, electronic structures, infrared (IR) spectra, and thermodynamic properties of the high energy density compound hexanitrohexaazatricyclotetradecanedifuroxan (HHTTD) at the B3LYP/6-31G** level of theory. The calculated results show that there are four conformational isomers (α, β, γ and δ) for HHTTD, and the relative stabilities of four conformers were assessed based on the calculated total energies and the energy-gaps between the frontier molecular orbitals. The computed harmonic vibrational frequencies are in reasonable agreement with the available experimental data. Thermodynamic properties derived from the IR spectra on the basis of statistical thermodynamic principles are linearly correlated with the temperature. Detonation performances were evaluated by using the Kamlet-Jacobs equations based on the calculated densities and heats of formation. It was found that four HHTTD isomers with the predicted densities of ca. 2 g•cm -3 , detonation velocities near 10 km•s -1 , and detonation pressures over 45 GPa, may be novel potential candidates of high energy density materials (HEDM). These results may provide basic information for the molecular design of HEDM.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the High Energy Density Compound Hexanitrohexaazatricyclotetradecanedifuroxan

Qiu¹,

Xiao²,

Zhu³

et al. 2006

Chin. J. Chem.

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show abstract

“…Some researchers investigated furazano [12][13][14] and tetrazole derivatives, 14,15 which belonged to fused systems with six-membered azacyclanes. Recently, a new designed furazano-fused seven-membered N-nitrated azacyclane, 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f ]-1,3,5-triazepine was reported.…”

Section: 11mentioning

confidence: 99%

Theoretical Investigation on the Structure, Detonation Performance and Pyrolysis Mechanism of 4,6,8-Trinitro-4,5,7,8-tetrahydro -6H-furazano[3,4-f]-1,3,5-triazepine

Li¹,

Zhang²,

Zhang³

2014

Bulletin of the Korean Chemical Society

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Based on the full optimized molecular geometric structures at B3LYP/cc-pvtz method, a new designed compound, 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f ]-1,3,5-triazepine was investigated in order to look for high energy density compounds (HEDCs). The analysis of the molecular structure indicates that the seven-membered ring adopts chair conformation and there exist intramolecular hydrogen bond interactions. IR spectrum and heat of formation (HOF) were predicted. The detonation velocity and pressure were evaluated by using Kamlet-Jacobs equations based on the theoretical density and condensed HOF. The bond dissociation energies and bond orders for the weakest bonds were analyzed to investigate the thermal stability of the title compound. The results show that N 1 -N 6 bond is the trigger bond. The crystal structure obtained by molecular mechanics belongs to Pna2 1 space group, with lattice parameters Z = 4, a = 15.3023 Å, b = 5.7882 Å, c = 11.0471 Å, ρ = 2.06 g cm . In addition, the analysis of frontier molecular orbital shows the title compound has good stability and high chemical hardness.

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“…Nucleophilic substitutions of tetrazines, in particular 3,6-bis(3,5-dimethylpyrazol-1yl)-1,2,4,5-tetrazine (1), have been studied extensively by us [10] and others [11,12]. Additionally, the nucleophilicity of 3,4-diamino-1,2,5-oxadiazole (2) has been studied as well [13], but there exist no literature examples describing the reactivity of 1 with 2 or any other tetrazine. We began our investigations by studying the substitution reaction of 1 with 2.…”

Section: Introductionmentioning

confidence: 99%

New heterocycles from tetrazines and oxadiazoles

Chávez

Parrish

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).The reactivity of 3,4-diamino-1,2,5-oxadiazole (2) toward nucleophilic substitution of 3,6-bis(3,5-dimethylpyrazol-1yl)-1,2,4,5-tetrazine (1) was studied. A new class of high nitrogen heterocyclic systems was prepared. It was determined that 3,4-diamino-1,2,5-oxadiazole did not display the required nucleophilicity to be reactive. However, the anion of 3,4-diamino-1,2,5-oxadiazole, prepared by treatment with strong base, was sufficiently reactive to act as a nucleophile.

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Synthesis and chemistry of some furazano- and furoxano[3,4-b]piperazines

Cited by 65 publications

References 0 publications

Theoretical Study on the High Energy Density Compound Hexanitrohexaazatricyclotetradecanedifuroxan

Theoretical Study on the High Energy Density Compound Hexanitrohexaazatricyclotetradecanedifuroxan

Theoretical Investigation on the Structure, Detonation Performance and Pyrolysis Mechanism of 4,6,8-Trinitro-4,5,7,8-tetrahydro -6H-furazano[3,4-f]-1,3,5-triazepine

New heterocycles from tetrazines and oxadiazoles

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