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首页> 外文期刊>Chemistry: A European journal >New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles
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New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles

机译：新型含能材料：功能化的1-乙基-5-氨基四唑和1-乙基-5-硝化四唑

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摘要

Alkylation of 5-aminotetrazole (1) with 2-chloroethanol leads to a mixture of the N-1 and N-2 isomers of (2-hydroxyethyl)-5-aminotetrazole. Treatment of 1-(2-hydroxyethyl)-5-aminotetrazole (2) with SOCl2 yielded 1- (2-chlorethyl)-5-aminotetrazole (3). 1- (2-Azidoethyl)-5-aminotetrazole (4) was generated by the reaction of 3 with sodium azide. Nitration of 2, 3, and 4 with HNO3 (100%) yielded in the case of 2 and 3 1-(2-hydroxyethyl)-5-nitriminotetrazole (5) and 1-(2-chloroethyl)-5- nitriminotetrazole (6). In the case of 4, 1-(2-nitratoethyl)-5-nitriminotetrazole monohydrate (7) was obtained. 1-(2- Azidoethyl)-5-nitriminotetrazole (8) could be obtained by nitration of 4 with NO2BF4 via the formation of potassium 1-(2-azidoethyl)-5-nitriminotetrazolate (9). The reaction of 6 with NaN3 resulted in the formation of the salt sodium 1-(2-chloroethyl)-5-nitriminotetrazolate (10 a). The deprotonation reaction of 6 was further investigated by the formation of the ammonium salt (10b). The protonation of 2 and 4 with dilute nitric acid led to 1-(2-hydroxyethyl)- 5-aminotetrazolium nitrate (11)and 1-(2-azidoethyl)-5-aminotetrazolium nitrate (12), respectively. Similarly, protonation of 4 with perchloric acid led to 1-(2-azidoethyl)-5-aminotetrazolium perchlorate monohydrate (13). Since 5-nitrimino-tetrazoles can be used as bidentate ligands, the coordination abilities of 5, 6, and 8 were tested by the reaction with copper nitrate trihydrate, yielding the copper complexes trans-[diaquabis{1-(2-hydroxyethyl)-5- nitriminotetrazolato-k2N4,O5}copper(II)] (14), trans-[diaquabis{1-(2-chloroethyl)- 5-nitriminotetrazolatok2N4,O5}copper(II)] dihydrate (15), and [diaquabis{1-(2-azidoethyl)-5-nitriminotetrazolato- k2N4,O5}copper(II)] (16). All compounds were characterized by low-temperature single-crystal X-ray diffraction. In addition, comprehensive characterization (IR, Raman, and multinuclear NMR spectroscopy (1H, 13C), elemental analysis, mass spectrometry, DSC) was performed. The heats of formation of selected compounds were computed by using heats of combustion obtained by bomb calorimetry or calculated by the atomization method. With these values and the densities determined from X-ray crystallography, several detonation parameter were calculated by the EXPLO5 program. Finally, the sensitivities towards impact and friction were determined using a BAMdrop hammer and friction tester.
机译：5-氨基四唑（1）与2-氯乙醇的烷基化反应生成（2-羟乙基）-5-氨基四唑的N-1和N-2异构体的混合物。用SOCl 2处理1-（2-羟乙基）-5-氨基四唑（2），得到1-（2-氯乙基）-5-氨基四唑（3）。 3与叠氮化钠反应生成1-（2-叠氮基乙基）-5-氨基四唑（4）。在2和3的情况下，用HNO3（100％）硝化2、3和4会生成1-（2-羟乙基）-5-硝三氨基四唑（5）和1-（2-氯乙基）-5-硝亚胺四唑（6 ）。在4的情况下，获得1-（2-硝基乙基）-5-硝基三氨基四唑一水合物（7）。 1-（2-叠氮基乙基）-5-硝氨基四唑（8）可通过与NO2BF4硝化4形成1-（2-叠氮基乙基）-5-硝氮四唑酸钾（9）获得。 6与NaN3的反应导致形成1-（2-氯乙基）-5-氮杂氨基四唑酸钠盐（10 a）。通过形成铵盐（10b）进一步研究了6的去质子反应。 2和4用稀硝酸质子化分别产生1-（2-羟乙基）-5-氨基四唑硝酸盐（11）和1-（2-叠氮基乙基）-5-氨基四唑硝酸盐（12）。同样，用高氯酸对4进行质子化反应，生成高氯酸1-（2-叠氮基乙基）-5-氨基四唑一水合物（13）。由于5-nitrimino-tetrazoles可用作二齿配体，因此通过与三水合硝酸铜的反应测试了5、6和8的配位能力，得到了反-[diaquabis {1-（2-羟乙基）- 5-水合亚硝基亚氨基四唑-k2N4，O5}铜（II）]（14），二水合反式[diaquabis {1-（2-氯乙基）-5-nitriminotetrazolatok2N4，O5}铜（II）]和[diaquabis { 1-（2-叠氮基乙基）-5-硝氨基四唑并-k2N4，O5}铜（II）]（16）。所有化合物均通过低温单晶X射线衍射表征。此外，还进行了综合表征（IR，拉曼光谱和多核NMR光谱（1H，13C），元素分析，质谱，DSC）。通过使用由炸弹量热法获得的或通过雾化方法计算的燃烧热来计算所选择的化合物的形成热。利用这些值和由X射线晶体学确定的密度，通过EXPLO5程序计算了几个爆轰参数。最后，使用BAMdrop锤和摩擦测试仪确定对冲击和摩擦的敏感度。

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