Citation: LI Shuailei, HU Yongpeng, HU Rongzu, MA Haixia. Crystal Structure and Thermal Behavior of 3-Nitroguanyl-6-(3,5-dimethylpyrazol-1yl)-1,2,4,5-tetrazine[J]. Chinese Journal of Applied Chemistry, ;2016, 33(1): 39-46. doi: 10.11944/j.issn.1000-0518.2016.01.150211 shu

Crystal Structure and Thermal Behavior of 3-Nitroguanyl-6-(3,5-dimethylpyrazol-1yl)-1,2,4,5-tetrazine

1.
a School of Chemical Engineering, Northwest University, Xi'an 710069, China;
2.
b Science and Technology on Combustion and Explosion Laboratory, Xi'an Modern Chemistry Research Institute, Xi'an 710065, China

Corresponding author: MA Haixia,
Received Date: 23 June 2015
Available Online: 17 September 2015
Fund Project:

3-Nitroguanyl-6-(3,5-dimethylpyrazol-1yl)-1,2,4,5-tetrazine(NDT) was synthesized and its crystal structure was determined by X-ray diffraction analysis. Crystals of NDT·DMF have the following parameters:triclinic, space group P-1, a=0.7070(4) nm, b=0.8468(6) nm, c=1.4123(9) nm, α=73.281(8)°, β=80.423(11)°, γ=81.740(9)°, Z=2. Thermal decomposition behavior of NDT was studied by DSC and TG-DTG analysis. The apparent activation energy and pre-exponential constant of the exothermic decomposition reaction were obtained as 288.25 kJ/mol and 10^29.04s^-1, respectively. The self-accelerating decomposition temperature(T_SADT), the thermal ignition temperature(T_be) and the critical temperature of thermal explosion(T_bp) are 212.19℃, 213.52℃ and 214.95℃, respectively. The adiabatic time-to-explosion was also estimated to be 5.43~6.26 s.
- nitroguanyl-(dimethylpyrazol-1yl)-tetrazine,
- crystal structure,
- thermal behavior,
- adiabatic time-to-explosion
1. [1]
  [1] Chavez D E,Hiskey M A,Naud D L.Tetrazine Exposives[J].Propell Explos Pyrot,2004,29(4):209-215.
2. [2]
  [2] Hiskey M A,Chavez D E.Insensitive High-Nitrogen Compounds:DE,2001776133[P],2001.
3. [3]
  [3] DONG Haishan.The Development and Countermeasure of High Energy Density Materials[J].Chinese J Energy Mater,2004,12:1-11(in Chinese).董海山.高能量密度材料的发展及对策[J].含能材料,2004,12:1-11.
4. [4]
  [4] JU Ronghui,FAN Xuezhong,WEI Hongjian,et al.Research Progress in Application of Tetrazine-based Energetic Compounds[J].Chem Propell Polym Mater,2013,11(4):23-28(in Chinese).巨荣辉,樊学忠,蔚红建,等.四嗪含能化合物的应用研究进展[J].化学推进剂与高分子材料,2013,11(4):23-28.
5. [5]
  [5] Ali A N,Son S F,Hiskey M A,et al.Novel High Nitrogen Propellant Use in Solid Fuel Micropropulsion[J].J Propul Power,2004,20(1):120-126.
6. [6]
  [6] FENG Jinling,ZHANG Jianguo,WANG Kun,et al.Crystal Structure and Theoretical Studies of 3,6-Dihydrazino-1,2,4,5-Tetrazine[J].Chem J Chinese Univ,2011,32(7):1519-1525(in Chinese).冯金玲,张建国,王昆,等.3,6-二肼基-1,2,4,5-四嗪的晶体结构及理论研究[J].高等学校化学报,2011,32(7):1519-1525.
7. [7]
  [7] Chavez D E,Hiskey M A,Gilardi R D.3,3'-Azobis (6-Amino-1,2,4,5-Tetrazine):A Novel High-Nitrogen Energetic Material[J].Angew Chem,2000,112(10):1861-1863.
8. [8]
  [8] Saikia A,Sivabalan R,Polke B G,et al.Synthesis and Characterization of 3,6-Bis (1H-1,2,3,4-tetrazol-5-ylamino)-1,2,4,5-tetrazine (BTATz):Novel High-Nitrogen Content Insensitive High Energy Material[J].J Hazard Mater,2009,170(1):306-313.
9. [9]
  [9] Son S F,Berghout H L,Bolme C A,et al.Burn Rate Measurements of HMX,TATB,DHT,DAAF,and BTATz[J].P Combust Inst,2000,28(1):919-924.
10. [10]
  [10] Chavez D E,Parrish D A.New Heterocycles from Tetrazines and Oxadiazoles[J].J Heterocycl Chem,2009,46(1):88-90.
11. [11]
  [11] Saracoglu N.Recent Advances and Applications in 1,2,4,5-Tetrazine Chemistry[J].Tetrahedron,2007,63(20):4199-4236.
12. [12]
  [12] Chavez D E,Hanson S K,Veauthier J M,et al.Electroactive Explosives:Nitrate Ester-Functionalized 1,2,4,5-Tetrazines[J].Angew Chem Int Edit,2013,52(27):6876-6879.
13. [13]
  [13] CHEN Hui,ZHENG Caixia,YANG Yufeng,et al.Synthesis and Anti-cancer Activities of Novel[1,2,4] Triazolo[4,3-b][1,2,4,5] Tetrazine Derivatives[J].Chinese J Synth Chem,2012,20(4):475-478(in Chinese).陈辉,郑彩霞,杨玉峰,等.新型[1,2,4] 三唑[4,3-b]均四嗪类化合物的合成及其抗癌活性[J].合成化学,2012,20(4):475-478.
14. [14]
  [14] YANG Zhenzhen,XU Feng,CHEN Hongyun,et al.Synthesis and Antitumor Activities of 6-(2-(1,2,4,5-tetrazin-3-yl) hydrazinyl)-1,3,5-Triazine Derivatives[J].Appl Chem Ind,2014,43(2):241-244(in Chinese).杨珍珍,徐峰,陈红云,等.6-[2-(1,2,4,5-四嗪-3-基)肼基]-1,3,5-三嗪类化合物的合成和抗肿瘤活性研究[J].应用化工,2014,43(2):241-244.
15. [15]
  [15] Zhao D,Lyu M F,Cai C.Study on the Azido-Tetrazolo Tautomerizations of 3,6-Bis (azido)-1,2,4,5-tetrazine[J].Propell Explos Pyrot,2015,40(5):627-631.
16. [16]
  [16] Coburn M D,Buntain G A,Harris B W,et al.An Improved Synthesis of 3,6-Diamino-1,2,4,5-Tetrazine.Ⅱ.From Triaminoguanidine and 2,4-Pentanedione[J].J Heterocycl Chem,1991,28(8):2049-2050.
17. [17]
  [17] MAI Tao.Synthesis,Characterization,Structural Analysis,Theoretical Calculations,Thermal Behavior and Thermodynamic Study of 1,2,4,5-Tetrazine Salts[D].Xi'an:Northwest University,2012(in Chinese).买涛.1,2,4,5-四嗪盐的合成、表征、结构解析、理论计算、热行为以及热力学研究[D].西安:西北大学,2012.
18. [18]
  [18] Chavez D E,Hiskey M A,Gilardi R D.Novel High-Nitrogen Materials Based on Nitroguanyl-Substituted Tetrazines[J].Org Lett,2004,6(17):2889-2891.
19. [19]
  [19] Sheldrick G M.SHELXS 97,Program for Crystal Structure Solution[CP],University of G ttingen,G ttingen,Germany,1997.
20. [20]
  [20] Sheldrick G M.SHELXL 97,Program for Crystal Structure Refinement[CP],University of G ttingen,G ttingen,Germany,1997.
21. [21]
  [21] HU Yongpeng,ZHAO Xufang,ZHAO Ningning,et al.Non-isothermal Thermal Decomposition Kinetics and Thermal Safety of DNGTz[J].Chinese J Energ Mater,2014,22(6):767-773(in Chinese).胡拥鹏,赵旭芳,赵宁宁,等.DNGTz的非等温热分解动力学及热安全性[J].含能材料,2014,22(6):767-773.
22. [22]
  [22] Kissinger H E.Reaction Kinetics in Differential Thermal Analysis[J].Anal Chem,1957,29(11):1702-1706.
23. [23]
  [23] Ozawa T.A New Method of Analyzing Thermogravimetric Data[J].Bull Chem Soc Jpn,1965,38(11):1881-1886.
24. [24]
  [24] MA Haixia,YAN Bao,LI Zhaona,et al.Preparation,Non-Isothermal Decomposition Kinetics,Heat Capacity and Adiabatic Time-to-Explosion of NTO DNAZ[J].J Hazard Mater,2009,169(1/2/3):1068-1073.
25. [25]
  [25] Zhang T L,Hu R Z,Xie Y,et al.The Estimation of Critical Temperature of Thermal Explosion for Energetic Materials Using Non-Isothermal DSC[J].Thermochim Acta,1994,244(2):171-176.
26. [26]
  [26] Zhang H,Xu K Z,Gao S,et al.Characterization and Thermal Properties of 2-(Dinitromethylene)-1,3-Diazacyclopentane Guanidine Salt[J].Indian J Chem,2013,52(4):473-479.
27. [27]
  [27] XU Kangzhen,ZUO Xian'gang,SONG Jirong,et al.Preparation,Crystal Structure and Thermal Behavior of K (FOX-7) H₂O[J].Chem J Chinese Univ,2010,31(4):638-643(in Chinese).徐抗震,左现刚,宋纪蓉,等.K (FOX-7)·H₂O的合成、晶体结构和热行为[J].高等学校化学报,2010,31(4):638-643.
1. [1]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
2. [2]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
3. [3]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
4. [4]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
5. [5]
  Yan Liu , Yuexiang Zhu , Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084
6. [6]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
7. [7]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
8. [8]
  Junqiao Zhuo , Xinchen Huang , Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100
9. [9]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
10. [10]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
11. [11]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
12. [12]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
13. [13]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
14. [14]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
15. [15]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
16. [16]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
17. [17]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
18. [18]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
19. [19]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
20. [20]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(280)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142