致密含能5,5'-二硝氨基-3,3'-偶氮-1,2,4-恶二唑及其盐的合成与潜在性能
Syntheses and Promising Properties of Dense Energetic 5,5'-Dinitramino-3,3'-azo-1,2,4-oxadiazole and Its Salts.
作者信息
Tang Yongxing, Gao Haixiang, Mitchell Lauren A, Parrish Damon A, Shreeve Jean'ne M
机构信息
Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, USA.
Department of Applied Chemistry, China Agricultural University, Beijing, 100193, China.
出版信息
Angew Chem Int Ed Engl. 2016 Feb 24;55(9):3200-3. doi: 10.1002/anie.201600068. Epub 2016 Jan 28.
Abstract
A planar energetic molecule with high density, 5,5'-dinitramino-3,3'-azo-1,2,4-oxadiazole (4), was obtained by the nitration of 5,5'-diamino-3,3'-azo-1,2,4-oxadiazole using 100 % nitric acid. In addition, selected nitrogen-rich salts were prepared. Of them, the neutral compound 4 and its hydroxylammonium salt, 6, were further confirmed by single-crystal X-ray diffraction. Physicochemical and energetic properties including density, thermal stability, and sensitivity were investigated. The energetic performance from the calculated heats of formation and experimental densities indicates that many of them have potential applications as energetic materials.
摘要
通过使用100%硝酸硝化5,5'-二氨基-3,3'-偶氮-1,2,4-恶二唑制备了一种具有高密度的平面含能分子5,5'-二硝氨基-3,3'-偶氮-1,2,4-恶二唑（4）。此外，还制备了一些含氮量高的盐。其中，中性化合物4及其羟铵盐6通过单晶X射线衍射进一步得到证实。研究了包括密度、热稳定性和感度在内的物理化学和含能性能。由计算的生成热和实验密度得出的含能性能表明，它们中的许多具有作为含能材料的潜在应用。
相似文献
1
Syntheses and Promising Properties of Dense Energetic 5,5'-Dinitramino-3,3'-azo-1,2,4-oxadiazole and Its Salts.致密含能5,5'-二硝氨基-3,3'-偶氮-1,2,4-恶二唑及其盐的合成与潜在性能
Angew Chem Int Ed Engl. 2016 Feb 24;55(9):3200-3. doi: 10.1002/anie.201600068. Epub 2016 Jan 28.
2
Boosting the Energetic Performance of Trinitromethyl-1,2,4-oxadiazole Moiety by Increasing Nitrogen-Oxygen in the Bridge.通过增加桥中的氮-氧来提高三硝基甲基-1,2,4-噁二唑部分的能量性能。
Int J Mol Sci. 2022 Sep 2;23(17):10002. doi: 10.3390/ijms231710002.
3
Enhancing Energetic Properties and Sensitivity by Incorporating Amino and Nitramino Groups into a 1,2,4-Oxadiazole Building Block.通过在 1,2,4-噁二唑砌块中引入氨基和硝氨基，提高能量特性和灵敏度。
Angew Chem Int Ed Engl. 2016 Jan 18;55(3):1147-50. doi: 10.1002/anie.201509985. Epub 2015 Nov 30.
4
Studies on the synthesis and properties of nitramino compounds based on tetrazine backbones.基于四嗪骨架的硝氨基化合物的合成与性能研究。
Dalton Trans. 2020 May 7;49(17):5590-5596. doi: 10.1039/c9dt04426d. Epub 2020 Apr 9.
5
Dense energetic nitraminofurazanes.致密高能硝氨基呋咱类化合物。
Chemistry. 2014 May 19;20(21):6401-11. doi: 10.1002/chem.201400362. Epub 2014 Apr 15.
6
Synthesis and Characterization of 2,2'-Dinitramino-5,5'-bi(1-oxa-3,4-diazole) and Derivatives as Economic and Highly Dense Energetic Materials.
Chemistry. 2017 Sep 7;23(50):12087-12091. doi: 10.1002/chem.201702191. Epub 2017 Jul 21.
7
Energetic furazan-triazole hybrid with dinitromethyl and nitramino groups: decreasing sensitivity via the formation of a planar anion.含二硝基甲基和硝氨基的高能呋咱-三唑杂化物：通过形成平面阴离子降低敏感度
Dalton Trans. 2019 Jun 14;48(22):7677-7684. doi: 10.1039/c9dt01514k. Epub 2019 May 7.
8
1,1'-Nitramino-5,5'-bitetrazoles.1,1'-二硝氨基-5,5'-联四唑
Chemistry. 2016 Mar 24;22(14):4966-70. doi: 10.1002/chem.201600177. Epub 2016 Feb 24.
9
Ammonia Oxide as a Building Block for High-Performance and Insensitive Energetic Materials.一氧化二氨：高性能、钝感含能材料的基石
Angew Chem Int Ed Engl. 2017 May 15;56(21):5894-5898. doi: 10.1002/anie.201702285. Epub 2017 Apr 24.
10
Exploiting the energetic potential of 1,2,4-oxadiazole derivatives: combining the benefits of a 1,2,4-oxadiazole framework with various energetic functionalities.开发1,2,4-恶二唑衍生物的能量潜力：将1,2,4-恶二唑骨架的优势与各种含能官能团相结合。
Dalton Trans. 2017 Oct 24;46(41):14210-14218. doi: 10.1039/c7dt03320f.
引用本文的文献
1
Monocyclic Bis(‑nitramine) Triazole: A High-Density Energetic Material with Exceptionally Weak N-N Bond.单环双（硝胺）三唑：一种具有异常弱N-N键的高密度含能材料。
JACS Au. 2025 Jun 26;5(7):3603-3611. doi: 10.1021/jacsau.5c00609. eCollection 2025 Jul 28.
2
Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives.用于大尺度研究炸药落锤冲击感度的化学描述符
J Chem Inf Model. 2023 Feb 13;63(3):753-769. doi: 10.1021/acs.jcim.2c01154. Epub 2023 Jan 25.
3
Simple and Efficient Synthesis of Diamino Derivatives of bis-1,2,4-oxadiazole Tandem Staudinger/aza-Wittig Reaction.双-1,2,4-噁二唑的二氨基衍生物的简单高效合成 通过Staudinger/aza-Wittig 串联反应。
Curr Org Synth. 2023;20(6):589-594. doi: 10.2174/1570179420666221006113032.
4
Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines.肟氯化物与 3,4-二氢异喹啉亚胺反应，简便合成三环 1,2,4-恶二唑啉并四氢异喹啉。
Molecules. 2022 May 10;27(10):3064. doi: 10.3390/molecules27103064.
5
Synthetic Strategies Toward Nitrogen-Rich Energetic Compounds the Reaction Characteristics of Cyanofurazan/Furoxan.富氮含能化合物的合成策略——氰基呋咱/呋咱的反应特性
Front Chem. 2022 Mar 17;10:871684. doi: 10.3389/fchem.2022.871684. eCollection 2022.
6
Nitrification Progress of Nitrogen-Rich Heterocyclic Energetic Compounds: A Review.富氮杂环含能化合物的硝化进展：综述
Molecules. 2022 Feb 22;27(5):1465. doi: 10.3390/molecules27051465.
7
New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan.通过调控三呋咱并氧化呋咱构型增强能量性能的新策略：3,4-双(3-硝基呋咱-4-基)呋咱并氧化呋咱
Sci Rep. 2019 Mar 13;9(1):4321. doi: 10.1038/s41598-019-39723-z.
8
Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-]indolone Derivatives.基于互变异构的腈氧化物与内酰胺环加成反应：1,2,4-恶二唑并[4,5-]吲哚酮衍生物的简便合成
ACS Omega. 2017 Jul 31;2(7):3123-3134. doi: 10.1021/acsomega.7b00490. Epub 2017 Jul 3.
本文引用的文献
1
Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe.核独立化学位移：一种简单高效的芳香性探针。
J Am Chem Soc. 1996 Jul 3;118(26):6317-6318. doi: 10.1021/ja960582d.
2
Potassium 4,5-Bis(dinitromethyl)furoxanate: A Green Primary Explosive with a Positive Oxygen Balance.四,五-双(二硝基甲基)呋咱基氧化钾：正氧平衡的绿色单质炸药。
Angew Chem Int Ed Engl. 2016 Jan 11;55(2):772-5. doi: 10.1002/anie.201509209. Epub 2015 Nov 6.
3
1,5-Di(nitramino)tetrazole: High Sensitivity and Superior Explosive Performance.1,5-二（硝氨基）四唑：高感度与优越的爆炸性能。
Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10299-302. doi: 10.1002/anie.201502919. Epub 2015 Jun 19.
4
Synthesis and structural characterization of 3,5-dinitro-1,2,4-triazolates.3,5-二硝基-1,2,4-三唑盐的合成与结构表征
Dalton Trans. 2015 Feb 21;44(7):2978-88. doi: 10.1039/c4dt03583f.
5
3,3'-Bi(1,2,4-oxadiazoles) featuring the fluorodinitromethyl and trinitromethyl groups.含有氟代二硝基甲基和三硝基甲基的3,3'-联（1,2,4-恶二唑）
Chemistry. 2014 Jun 16;20(25):7622-31. doi: 10.1002/chem.201402291. Epub 2014 May 7.
6
N-diazo-bridged nitroazoles: catenated nitrogen-atom chains compatible with nitro functionalities.N-重氮桥连硝基唑类：与硝基官能团兼容的连环氮原子链
Chemistry. 2014 May 26;20(22):6707-12. doi: 10.1002/chem.201402762. Epub 2014 Apr 24.
7
Maximum compaction of ionic organic explosives: bis(hydroxylammonium) 5,5'-dinitromethyl-3,3'-bis(1,2,4-oxadiazolate) and its derivatives.离子有机炸药的最大压实：双（羟铵）5,5'-二硝基甲基-3,3'-双（1,2,4-恶二唑）及其衍生物
Chemistry. 2014 Jan 27;20(5):1410-7. doi: 10.1002/chem.201303825. Epub 2013 Dec 27.
8
Synthesis and characterization of energetic 3-nitro-1,2,4-oxadiazoles.含能 3-硝基亚氧杂二唑的合成与表征。
Chemistry. 2012 Feb 13;18(7):1886-9. doi: 10.1002/chem.201103159. Epub 2012 Jan 20.
9
Multiwfn: a multifunctional wavefunction analyzer.Multiwfn：一款多功能波函数分析软件。
J Comput Chem. 2012 Feb 15;33(5):580-92. doi: 10.1002/jcc.22885. Epub 2011 Dec 8.
10
Azole-based energetic salts.基于唑类的含能盐。
Chem Rev. 2011 Nov 9;111(11):7377-436. doi: 10.1021/cr200039c. Epub 2011 Aug 12.
Zotero 插件