C6N10O4: Thermally Stable Nitrogen-Rich Inner Bis(diazonium) Zwitterions

被引：16
|
作者：
Tang, Yongxing [1 ]
Imler, Gregory H. [2 ]
Parrish, Damon A. [2 ]
Shreeve, Jean'ne M. [1 ]
机构：
[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA
[2] Naval Res Lab, 4555 Overlook Ave, Washington, DC 20375 USA
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 20期
关键词：
ENERGETIC DERIVATIVES; DIAZONIUM SALTS; PERFORMANCE;
D O I：
10.1021/acs.orglett.9b02875
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two nitrogen-rich inner bis(diazonium) salts, the 4,4'-dinitro-5,5'-diazo-2,2'-bisimidazole (2) and the 4,4'-dinitro-5,5'-diazo-3,3'-bispyrazole (4) zwitterions, are described. Compound 2 was synthesized unexpectedly from the nitration of 4,4'-dinitro-5,5'-diamino-1H,1'H-2,2'-bisimidazole (1) in a mixture of trifluoroacetic anhydride and 100% nitric acid. Both 2 and 4 show good thermal stability, especially 2 has, a decomposition temperature of 199 degrees C, which is the highest one in any of the reported hydrogen-free nitrogen-rich diazonium salts.
引用
收藏
页码：8201 / 8204
页数：4
相关论文
共 50 条
  • [1] A COMPUTATIONAL INVESTIGATION ON THE NITROGEN-RICH C2N10, C6N12, AND C6N20 COMPOUNDS BY DENSITY FUNCTIONAL METHODS
    Zhao, Run-Ning
    Han, Cun-Shan
    Chen, Rui
    Lu, Zi Chen
    Han, Ju-Guang
    REVUE ROUMAINE DE CHIMIE, 2018, 63 (01) : 21 - 30
  • [2] Synthesis and characterization of thermally stable energetic complexes with 3,5-diaminopyrazolone-4-oxime as a nitrogen-rich ligand
    Zhang, Lu
    Dong, Wen-Shuai
    Lu, Zu-Jia
    Wang, Ting-Wei
    Zhang, Chao
    Zhou, Zun-Ning
    Zhang, Jian-Guo
    CRYSTENGCOMM, 2022, 24 (30) : 5519 - 5526
  • [3] Thermodynamically stable polymorphs of nitrogen-rich carbon nitrides: a C3N5 study
    Ghasemi, S. Alireza
    Mirhosseini, Hossein
    Kuehne, Thomas D.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (11) : 6422 - 6432
  • [4] DFT THEORETICAL STUDY OF ENERGETIC NITROGEN-RICH C4N6H8-n(NO2)n DERIVATIVES
    Jin, Xinghui
    Hu, Bingcheng
    Jia, Huanqing
    Liu, Zuliang
    Lu, Chunxu
    QUIMICA NOVA, 2014, 37 (01): : 74 - 80
  • [5] Carbon and nitrogen speciation in nitrogen-rich C-O-H-N fluids at 5.5-7.8 GPa
    Sokol, Alexander G.
    Palyanov, Yury N.
    Tomilenko, Anatoly A.
    Bul'bak, Taras A.
    Palyanova, Galina A.
    EARTH AND PLANETARY SCIENCE LETTERS, 2017, 460 : 234 - 243
  • [6] Stable structures of nitrogen-rich sulfides:: S(N3)m (m=1-4)
    Wang, LJ
    Zgierski, MZ
    Mezey, PG
    JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (12): : 2080 - 2084
  • [7] Ti(N5)4 as a Potential Nitrogen-Rich Stable High-Energy. Density Material
    Choi, Changhyeok
    Yoo, Hae-Wook
    Goh, Eun Mee
    Cho, Soo Gyeong
    Jung, Yousung
    JOURNAL OF PHYSICAL CHEMISTRY A, 2016, 120 (24): : 4249 - 4255
  • [8] DFT Theoretical Study on Nitrogen-rich Compounds C6H6-n(N3)n(n=1-6)
    Liu Xiao-Fang
    Xu Wen-Guo
    Lu Shi-Xiang
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2009, 30 (07): : 1406 - 1409
  • [9] Stable structures of nitrogen-rich sulfides:: N3SN4 and S(N4)m (m=1-4)
    Wang, LJ
    Mezey, PG
    Zgierski, MZ
    CHEMICAL PHYSICS LETTERS, 2003, 369 (3-4) : 386 - 393
  • [10] Fluorescent nitrogen-rich carbon nanodots with an unexpected β-C3N4 nanocrystalline structure
    Messina, F.
    Sciortino, L.
    Popescu, R.
    Venezia, A. M.
    Sciortino, A.
    Buscarino, G.
    Agnello, S.
    Schneider, R.
    Gerthsen, D.
    Cannas, M.
    Gelardi, F. M.
    JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (13) : 2598 - 2605
12345