New Energetic Materials featuring Tetrazoles and Nitramines – Synthesis, Characterization and Properties

Fischer, Niko; Karaghiosoff, Konstantin; Klapötke, Thomas M.; Stierstorfer, Jörg

doi:10.1002/zaac.200900521

Cited by 64 publications

(45 citation statements)

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“…The DFT(M06‐2X)/TZVP+‐optimized geometries of 1 – 6 (Figure ) are in good agreement with the published X‐ray crystal structures . WBIs were calculated from the optimized structures and compared to reference molecules (Table ) in order to determine potential trigger bonds.…”

Section: Resultssupporting

confidence: 68%

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis

2015

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Understanding the explosive decomposition pathways of high-energy-density materials (HEDMs) is important for developing compounds with improved properties. Rapid reaction rates make the detonation mechanisms of HEDMs difficult to understand, so computational tools are used to predict trigger bonds-weak bonds that break, leading to detonation. Wiberg bond indices (WBIs) have been used to compare bond densities in HEDMs to reference molecules to provide a relative scale for the bond strength to predict the activated bonds most likely to break to trigger an explosion. This analysis confirms that X-NO2 (X=N,C,O) bonds are trigger linkages in common HEDMs such as TNT, RDX and PETN, consistent with previous experimental and theoretical studies. Calculations on a small test set of substituted tetrazoles show that the assignment of the trigger bond depends upon the functionality of the material and that the relative weakening of the bond correlates with experimental impact sensitivities.

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Section: Resultssupporting

confidence: 68%

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis

2015

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“…[4][5][6] The unique stability of dinitrogen that arises from its strong, short, triple bond means that the decomposition of high-nitrogen compounds with the formation of nitrogen gas is highly favored energetically, thus making nitrogen-rich compounds one intensely pursued strategy in the design of energetic materials. [7][8][9] For a nitrogen-rich material to find practical use as a high explosive, it needs to possess high thermal and mechanical stabilities while concurrently satisfying the demand for ever higher-performing materials. As the nitrogen content of a material rises, the heat of formation also rises, and concurrently the energetic performance.…”

Section: Introductionmentioning

confidence: 99%

The Taming of CN₇⁻: The Azidotetrazolate 2‐Oxide Anion

Klapötke

Piercey

Stierstorfer

2011

Chemistry A European J

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114

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The highly sensitive 5-azidotetrazolate anion was oxidized to its corresponding N-oxide by aqueous oxidation in a buffered oxone solution to the azidotetrazolate 2-oxide anion. After acidic extraction and neutralization with ammonia, the ammonium salt was isolated. Several energetic salts of this novel anion were prepared from the ammonium salt, and in all cases were found to be of lower sensitivity than the corresponding 5-azidotetrazolate salt while still being highly sensitive towards mechanical stimuli. Explosive performances (detonation velocity, detonation pressure) of applicable salts were also found to be higher than the non-N-oxide variants. Preparation of the free acid 2-hydroxy-5-azidotetrazole was achieved by protonation of the anion and identified by NMR spectroscopy, whereas the majority of the azidotetrazolate 2-oxide salts have unequivocal crystallographic proof.

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“…The groups of C-NO 2 , N-NO 2 , or O-NO 2 are the most common forms of this moiety in energetic compounds [1][2][3][4]. Nitroimino compounds have attracted a continuous attention for their rather high nitrogen content, high densities, good oxygen balance, high heats of formation and reasonable sensitivities [5][6][7][8][9][10][11] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of 5-Amino-1-nitriminotetrazole and Its Salts

Liu

et al. 2012

J Chem Crystallogr

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New nitrogen-rich energetic compound 5-amino-1-nitriminotetrazole (2) and its ammonium (3), hydrazinium (4) salts have been prepared. Their structures were characterized and confirmed by 1 H NMR spectroscopy, IR spectroscopy, elemental analysis and ESI-MS, X-ray single-crystal diffraction. Compound 2 crystallizes in the orthorhombic Pna2(1) space group with unit cell parameters are a = 9.229 (2) Å , b = 5.5271 (13) Å , c = 10.295(2) Å , V = 525.1(2) Å 3 , Z = 4. Compound 3 crystallizes in the Monoclinic C2/c space group, its unit cell parameters are a = 25.932 (6) Å , b = 6.8844(15) Å , c = 14.006(3) Å , b = 102.052(3), V = 2445.3(10) Å 3 , Z = 16. Compound 4 crystallizes in the Monoclinic P2(1)/c space group with unit cell parameters are a = 7.275(3) Å , b = 14.273(5) Å , c = 6.802(2) Å , b = 97.009(5) Å , V = 701.0(4) Å 3 , Z = 4. Extensive hydrogen bonds of these compounds packed a 3D network. Finally, the influences of molecular structure on the properties of the new compounds were discussed.

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New Energetic Materials featuring Tetrazoles and Nitramines – Synthesis, Characterization and Properties

Abstract: Abstract. The alkylation of 2-nitro-2-azapropyl chloride (2) and deprotonated 5-amino-1H-tetrazole (3), 1H-tetrazole (4), 5-nitrimino-1,4H-tetrazole (5), 1-methyl-5-nitrimino-

Cited by 64 publications

References 45 publications

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis

The Taming of CN₇⁻: The Azidotetrazolate 2‐Oxide Anion

Synthesis and Characterization of 5-Amino-1-nitriminotetrazole and Its Salts

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New Energetic Materials featuring Tetrazoles and Nitramines – Synthesis, Characterization and Properties

Abstract: Abstract. The alkylation of 2-nitro-2-azapropyl chloride (2) and deprotonated 5-amino-1H-tetrazole (3), 1H-tetrazole (4), 5-nitrimino-1,4H-tetrazole (5), 1-methyl-5-nitrimino-

Cited by 64 publications

References 45 publications

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis

Predicting Trigger Bonds in Explosive Materials through Wiberg Bond Index Analysis

The Taming of CN7−: The Azidotetrazolate 2‐Oxide Anion

Synthesis and Characterization of 5-Amino-1-nitriminotetrazole and Its Salts

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The Taming of CN₇⁻: The Azidotetrazolate 2‐Oxide Anion