Synthesis and Characterization of a Stable, Catenated N<sub>11</sub> Energetic Salt

Tang, Yongxing; Yang, Hongwei; Wu, Bo; Ju, Xue‐Hai; Lu, Chunmei

doi:10.1002/anie.201300117

Cited by 114 publications

(57 citation statements)

References 29 publications

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“…17 Initially, 3H-tetrazolo[1, 5-d]tetrazole (5,Scheme 6) with the N 7 structure aroused our interest. 18 Our attempts to prepare 5 following the reported literature procedure failed by treatment of DAT with sodium nitrite in concentrated HCl solution.…”

Section: Scheme 5 Extending the Nitrogen Chain By Substitution Reactionmentioning

confidence: 99%

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Yang

Cheng

Tang

2013

Synlett

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The synthesis and handling of compounds containing long catenated nitrogen chains are challenging for researchers in this field. These challenges arise from their high endothermic, thermodynamic instability, and a serious lack of nitrogen-nitrogen bond-forming reactions. This paper addresses techniques of azocoupling reaction between the diazonium salt of N-NH 2 and amine derivative to form the longest nitrogen chain (N 11 ). This type of nitrogen-nitrogen bond formation opens a new strategy for the construction of novel compounds containing odd or even numbers of catenated nitrogen atoms (≥9) especially for polynitrogen compounds.Key words: azo coupling, energetic materials, catenated nitrogenatom chain, formation of nitrogen-nitrogen bond, tetrazole Compounds containing long catenated nitrogen-atom chains and polynitrogen compounds are attracting and challenging in research areas such as propellants, explosives, and pyrotechnics. This attraction is due to their high heat of formation and environmentally bening decomposition products of nitrogen gas.However, there are also two challenges in synthesizing and handling high nitrogen compounds containing directly linked N-N single or double bonds for chemists in this fascinating field. One arises from their high endothermic and thermodynamic unstability. The triple bond in molecular nitrogen (N 2 ) with 942 kJ/mol bond energy is characterized as the strongest bond in nature. The sum of the bond energies of the N-N single and double bonds possesses much less than that of triple bonds. As a result, energetic compounds containing catenated N-N single and double bonds could be easily triggered to produce diatomic nitrogen gas accompanied by a very large energy release. 2 Therefore, the larger the string of the catenated nitrogen-nitrogen bond, the more unstable the compound is. The other challenge results from a serious lack of nitrogen-nitrogen bond-forming reactions in comparison with carbon analogues. With the development of synthetic organic chemistry, chemists have a wealth of methods to construct C-C and C-N bonds. In comparison, methods for the synthesis of nitrogen-nitrogen bonds are extremely limited.

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Section: Scheme 5 Extending the Nitrogen Chain By Substitution Reactionmentioning

confidence: 99%

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Yang

Cheng

Tang

2013

Synlett

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“…Energetic materials, focusingo np ropellants, explosives, and pyrotechnics, are continuously the focus of intense research interests in chemicala nd materials cience [1][2][3][4][5][6][7][8] as they have made great contributions to the development of civilian and military areas. With the increaseo fa pplication requirements, conventional insensitive explosives 2,4,6-triamino-1,3,5-trinitrobenzene (TATB) or classical high-energetic explosives such as 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) and 2,4,6,8,10,4,6,8,10,, which are both individual organic backbones constructed from simple elements of C, H, O, and N, leave much room for improvement because they exhibit either the insufficient energetic performance or poor safety properties.…”

Section: Introductionmentioning

confidence: 99%

Study of Six Green Insensitive High Energetic Coordination Polymers Based on Alkali/Alkali‐Earth Metals and 4,5‐Bis(tetrazol‐5‐yl)‐2 H‐1,2,3‐triazole

Chen

Dong

Zhang

et al. 2017

Chemistry An Asian Journal

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Constructing insensitive high-performance energetic coordination polymers (ECPs) with alkali/alkali-earth metal ions and a nitrogen-rich organic backbone has been proved to be a feasible strategy in this work. Six diverse dimensional novel ECPs (compounds 1-6) were successfully synthesized from Na , Cs , Ca , Sr , Ba ions and a nitrogen-rich triheterocyclic 4,5-bis(tetrazol-5-yl)-2 H-1,2,3-triazole (H BTT). All compounds show outstanding stability and low sensitivity, the thermal stability of these ECPs are significantly improved as the structural reinforcement increases from 1D to 3D, in which the decomposition temperature of 3D Ba based compound 6 is as high as 397 °C. Long-term storage experiments show that compounds 5 and 6 are stable enough at high temperature. Moreover, the six compounds hold considerable detonation performances, in which Ca based compound 5 possesses the detonation velocity of 9.12 km s , along with the detonation pressure of 34.51 GPa, exceeding those of most energetic coordination polymers. Burn tests further certify that the six compounds can be versatile pyrotechnics.

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“…[1][2][3][4][5][6][7][8][9][10][11] However, high energy and low sensitivity requirements are often contradictory, making the development of new EMs difficult and challenging. [1][2][3][4][5][6][7][8][9][10][11] We aim here to provide the synthetic chemists a simple tool for predicting the sensitivity prior to the often complex and time consuming process of synthesizing new generations of EMs.…”

Section: Introductionmentioning

confidence: 99%

Reaction mechanisms and sensitivity of silicon nitrocarbamate and related systems from quantum mechanics reaction dynamics

et al. 2018

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Synthesis and Characterization of a Stable, Catenated N₁₁ Energetic Salt

Cited by 114 publications

References 29 publications

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Study of Six Green Insensitive High Energetic Coordination Polymers Based on Alkali/Alkali‐Earth Metals and 4,5‐Bis(tetrazol‐5‐yl)‐2 H‐1,2,3‐triazole

Reaction mechanisms and sensitivity of silicon nitrocarbamate and related systems from quantum mechanics reaction dynamics

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Synthesis and Characterization of a Stable, Catenated N11 Energetic Salt

Cited by 114 publications

References 29 publications

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds

Study of Six Green Insensitive High Energetic Coordination Polymers Based on Alkali/Alkali‐Earth Metals and 4,5‐Bis(tetrazol‐5‐yl)‐2 H‐1,2,3‐triazole

Reaction mechanisms and sensitivity of silicon nitrocarbamate and related systems from quantum mechanics reaction dynamics

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Synthesis and Characterization of a Stable, Catenated N₁₁ Energetic Salt