5-(1H-Tetrazolyl)-2-Hydroxy-Tetrazole: A Selective 2N-Monoxidation of Bis(1H-Tetrazole)

Klapoetke Thomas M.; Kurz Matthias Q.; Scharf Regina; Schmid Philipp C.; Stierstorfer Joerg; Suceska Muhamed

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5-(1H-Tetrazolyl)-2-Hydroxy-Tetrazole: A Selective 2N-Monoxidation of Bis(1H-Tetrazole)

机译：5-（1H-四唑基）-2-羟基 - 四唑：双（1H-四唑）的选择性2N单氧化

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摘要

Sodium 5-cyanotetrazolate sesquihydrate (1) is prepared from sodium azide and two equivalents of sodium cyanide under acidic conditions. 1 is then N-oxidized with Oxone to sodium 5-cyanotetrazolate monohydrate (2). Compound 2 is treated with sodium azide and a Lewis acid to form 5-(1H-tetrazolyl)-2-hydroxytetrazole monohydrate (3). Compound 3 can be deprotonated twice by various bases to give ionic derivatives such as the bis(hydroxylammonium) (4), bis(hydrazinium) (6), bis(guanidinium) (7), bis(aminoguanidinium) (8), bis(ammonium) (9), and diaminouronium (11) salt. In addition, compound 3 can only be deprotonated once, as demonstrated by the hydroxylammonium (4) and triaminoguanidinium (10) salts. Compounds 2-5 and 10-11 are structurally characterized by single-crystal X-ray diffraction. Additionally, compounds 2-11 are characterized by using NMR and vibrational (IR, Raman) spectroscopy as well as mass spectrometry and elemental analysis. Their thermal behaviors are studied from differential thermal analysis measurements, and the sensitivities of the compounds toward shock, friction, and electrostatic discharge are determined. In addition, the heats of formation are calculated (atomization method, CBS-4M enthalpies), and several detonation/propulsion parameters are computed with the EXPLO5 code.

机译：将5-氰基四醇钠溶质水合物（1）由氧化钠和氰化钠在酸性条件下制备。然后将1用氧化钠N-氧化至5-氰基四甲酸钠一水合物（2）。化合物2用叠氮化钠和路易斯酸处理，形成5-（1H-四唑基）-2-羟基一氢一水合物（3）。化合物3可以通过各种碱基化两次去除两次，得到离子衍生物，例如双（羟基铵）（4），双（肼鎓）（6），双（胍））（7），双（氨基胍）（8），BIS（铵）（9）和二氨基（11）盐。此外，化合物3只能由羟基（4）和Triaminoguanidinium（10）盐所证明的一次脱质。化合物2-5和10-11通过单晶X射线衍射在结构表征。另外，化合物2-11的特征在于使用NMR和振动（IR，拉曼）光谱以及质谱和元素分析。从差分热分析测量中研究了它们的热行为，并且确定了化合物对冲击，摩擦和静电放电的敏感性。此外，计算形成的形成热量（雾化方法，CBS-4M焓），并使用Explo5代码计算多个爆轰/推进参数。

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来源
《ChemPlusChem》 |2015年第1期|共10页
作者
Klapoetke Thomas M.; Kurz Matthias Q.; Scharf Regina; Schmid Philipp C.; Stierstorfer Joerg; Suceska Muhamed;
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作者单位

Univ Munich Dept Chem D-81377 Munich Germany;

Univ Munich Dept Chem D-81377 Munich Germany;

Univ Munich Dept Chem D-81377 Munich Germany;

Univ Munich Dept Chem D-81377 Munich Germany;

Univ Munich Dept Chem D-81377 Munich Germany;

Brodarski Inst Zagreb 10000 Croatia;

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正文语种 eng
中图分类化学;
关键词
energetic materials; heterocycles; N-oxides; tetrazoles; X-ray diffraction;

机译：精力充沛的材料;杂环;N-氧化物;四唑;X射线衍射;

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5-(1H-Tetrazolyl)-2-Hydroxy-Tetrazole: A Selective 2N-Monoxidation of Bis(1H-Tetrazole)

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