Synthesis and Characterization of Binary, Highly Endothermic, and Extremely Sensitive 2,2′-Azobis(5-azidotetrazole)

IF 14.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Journal of the American Chemical Society Pub Date : 2022-03-31 DOI:10.1021/jacs.2c00995
Maximilian Benz, Thomas M. Klapötke*, Jörg Stierstorfer and Michael Voggenreiter, 
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引用次数: 21

Abstract

2,2′-Azobis(5-azidotetrazole) (C2N16, 3), a highly energetic nitrogen-rich binary CN compound was obtained in a three-step synthesis through the formation of 5-azidotetrazole (1), subsequent amination using O-tosylhydroxylamine to give 2-amino-5-azidotetrazole (2), and oxidative azo coupling of 2 using tBuOCl as an oxidant in MeCN. A nitrogen:carbon ratio of 8:1, eight nitrogen atoms in a row, and a nitrogen content of over 90% was unknown for a binary heterocyclic compound until now. The successful isolation was confirmed through X-ray diffraction as well as by vibrational and 13C NMR spectroscopy. C2N16 can explode instantly and shows mechanical sensitivities far higher than quantitatively measurable. Nevertheless, it features interesting energetic performances, which were calculated using different quantum-chemical methods.

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二元、高吸热、极敏感的2,2′-偶氮杂氮(5-叠氮四唑)的合成与表征。
2,2'-偶氮二(5-叠氮四唑)(C2N16,3)是一种高能富氮的二元CN化合物,通过形成5-叠氮五唑(1),随后使用O-甲苯磺酰基羟胺胺化得到2-氨基-5-叠氮四噻唑(2),并使用tBuOCl作为MeCN中的氧化剂氧化偶氮偶联2,通过三步合成得到。氮碳比为8:1,连续八个氮原子,氮含量超过90%,对于二元杂环化合物来说,直到现在都是未知的。通过X射线衍射以及振动和13C NMR光谱证实了成功的分离。C2N16可以立即爆炸,并且显示出远高于定量测量的机械灵敏度。然而,它具有有趣的能量性能,这些性能是使用不同的量子化学方法计算的。
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来源期刊
CiteScore
24.40
自引率
6.00%
发文量
2398
审稿时长
1.6 months
期刊介绍: The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
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