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Synthesis and Characterization of N5‐(2‐Fluoro‐2,2‐dinitroethyl)‐N1‐methyl‐1H‐tetrazole‐5‐amine and its Nitramide Based on Functionalized Amino Group in 5‐Amino‐1H‐tetrazole
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-06-26 , DOI: 10.1002/slct.201800854
Jie Li 1, 2 , Guojie Zhang 1, 3 , Zhenqi Zhang 1 , Qing Ma 1 , Guijuan Fan 1 , Shuihua Tang 2
Affiliation  

N5‐(2‐fluoro‐2,2‐dinitroethyl)‐N1‐methyl‐1H‐tetrazole‐5‐amine and its nitramide were designed and synthesized by a strategy based on functionalized amino group in 5‐amino‐1H‐tetrazole. Their structures were fully determined by 1H, 13C NMR, infrared spectrum as well as elementary analysis. Single‐crystal X‐ray diffraction was employed for characterizing their crystal structures. Comparing with its nitramide N5‐(2‐fluoro‐2,2‐dinitroethyl)‐N1‐methyl‐1H‐tetrazol‐5‐yl)‐nitramide (Tm: 76 oC, Td: 135 oC, Tp: 163 oC), N5‐(2‐fluoro‐2,2‐dinitroethyl)‐N1‐methyl‐1H‐tetrazole‐5‐amine exhibits better thermal stability (Tm: 167 oC, Td: 191 oC, Tp: 205 oC), which is superior to those of N3,N4‐bis(2‐fluoro‐2,2’‐dinitroethyl)‐1,2,5‐oxadiazole‐3,4‐diamine (LLM‐208) (Tm: 149 oC, Tp: 188 oC). They both present insensitivity towards impact but slightly sensitive to friction. It is worth noting that N5‐(2‐fluoro‐2,2‐dinitroethyl)‐N1‐methyl‐1H‐tetrazol‐5‐yl)‐nitramide shows its detonation performance approaching those of RDX. The above‐mentioned energetic performance show that they are insensitive and worth further potential applications as oxidizers, melt‐cast explosives, energetic plasticizers, or high‐performance ligands for constructing energetic coordination polymers.

中文翻译:

N5-(2-氟-2-,2-二硝基乙基)-N1-甲基-1H-四唑-5-胺及其在5-氨基-1H-四唑中基于官能团氨基的硝酰胺的合成和表征

N 5-(2-氟-2-,2-二硝基乙基)-N 1-甲基-1H-四唑-5-胺及其硝酰胺是通过基于5-氨基-1H-四唑中官能团氨基的策略设计和合成的。它们的结构通过1 H,13 C NMR,红外光谱以及元素分析完全确定。单晶X射线衍射用于表征其晶体结构。与其硝酰胺N 5-(2-氟-2-,2-二硝基乙基)-N 1-甲基-1H-四唑-5-基)硝酰胺(T m:76 o C,T d:135 o C,T p:163o C),N 5-(2-氟-2-,2-二硝基乙基)-N 1-甲基-1H-四唑-5-胺表现出更好的热稳定性(T m:167 o C,T d:191 o C,T p:205 o C),优于N 3,N 4-双(2-氟-2-,2'-二硝基乙基)-1,2,5-恶二唑-3,4-二胺(LLM- 208)(T m:149 o C,T p:188 o C)。它们都对撞击不敏感,但对摩擦稍敏感。值得注意的是N 5-(2-氟-2-2,2-二硝基乙基)-N 1-甲基-1H-四唑-5-基)-硝酰胺显示出接近RDX的爆炸性能。上述高能性能表明它们不敏感,值得作为氧化剂,熔体炸药,高能增塑剂或用于构造高能配位聚合物的高性能配体进一步应用。
更新日期:2018-06-26
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