Novel High-nitrogen Energetic Compound Based on Semicarbazide-substituted Tetrazine

Abstract

Abstract:

A novel energetic compound 3-(3,5-dimethylpyrazol-1-yl)-6-semicarbazide-1,2,4,5-tetrazine(DSTZ) was prepared and characterized by elemental analysis and Fourier transform infrared(FTIR) spectroscopy. The crystal structure was determined by X-ray single crystal diffraction technology. The crystal belongs to the monoclinic system with a P2₁/c space group, a=0.9942(7) nm, b=0.5067(3) nm, c=1.1830(8) nm, β=109.616°, Z=2 and D_c=1.475 g/cm³. With extensive hydrogen bonds, the molecules were linked together to form a three-dimensional herringbone-like pattern. Thermal analysis of the compound was carried out via differential scanning calorimetry(DSC) and thermogravimetric-derivative thermogravimetry(TG-DTG). Under a nitrogen atmosphere at a heating rate of 10 K/min, DSTZ decomposed directly in a range of 493-513 K. Only one intense exothermic process was observed and the decomposition products were all gaseous products. Conventional sensitivity properties were determined, showing that the title complex was insensitive to friction, impact and flame.

Key words: 1,2,4,5-Tetrazine, Semicarbazide, Crystal structure, Sensitivity property

ZHANG Jian-guo, LIANG Yan-hui, XIE Shao-hua, FENG Jin-ling, WANG Kun, ZHANG Tong-lai. Novel High-nitrogen Energetic Compound Based on Semicarbazide-substituted Tetrazine[J]. Chemical Research in Chinese Universities, 2012, 28(6): 931-935.

References

[1] Chavez D. E., Hiskey M. A., Gilardi R. D., Angew. Chem. Int. Ed., 2000, 39, 1791

[2] Talawar M. B., Sivabalan R., Senthilkumar N., Prabhu G., Asthana S. N., J. Hazard. Mater., 2004, 113, 11

[3] Huynh M. H. V., Hiskey M. A., Chavez D. E., Naud D. L., Gilard R. D., J. Am. Chem. Soc., 2005, 127, 12537

[4] Saracoglu N., Tetrahedron, 2007, 63, 4199

[5] Rahanyan N., Linden A., Baldridge K. K., Siegel J. S., Org. Biomol. Chem., 2009, 7, 5273

[6] Lorincz K., Kotschy A., Tammiku-Taul J., Sikk L., Burk P., J. Org. Chem., 2010, 75, 6196

[7] Dumas-Verdes C., Miomandre F., Lepicier E., Galangau O., Vu T. T., Clavier G., Eur. J. Org. Chem., 2010, 13, 2525

[8] Feng J. L., Zhang J. G., Wang K., Zhang T. L., Chem. J. Chinese Universities, 2011, 32(7), 1519

[9] Kaim W., Coord. Chem. Rev., 2002, 230, 127

[10] Turker L., Atalar T., Guemues S., CamurY., J. Hazard. Mater., 2009, 167, 440

[11] Yi J. H., Zhao F. Q., Wang B. Z., Liu Q., Zhou C., Hu R. Z., Ren Y. H., Xu K. Z., Ren X. N., J. Hazard. Mater., 2010, 181, 432

[12] Sayed A. R., Wiggins J. S., J. Appl. Polym. Sci., 2009, 114, 3915

[13] Wei T., Zhu W. H., Zhang X. W., Li Y. F., Xiao H. M., J. Phys. Chem. A, 2009, 113, 9404

[14] Hu W. X., Xu F., J. Heterocycl. Chem., 2008, 45, 1745

[15] Bostai B., Novak Z., Benyei A. C., Kotschy A., Org. Lett., 2007, 9, 3437

[16] Saracoglu N., Tetrahedron, 2007, 63, 4199

[17] Rusinov G. L., Latosh N. I., Ishmetova R. I., Kravchenko M. A., Ganebnykh I. N., Sokolov V. A., Chupakhin O. N., Pharm. Chem. J., 2005, 39, 8

[18] Cobum M. D., Buntain G. A., Harris B. W., J. Hetrocyclic. Chem., 1991, 28, 2049

[19] Xu S. L., Lei Y. P., Yang S. Q., Zhang W., Chin. J. Energ. Mater., 2006, 14, 340

[20] Kerth J., Lobbecke S., Propellants Explos. Pyrotech., 2002, 27, 111

[21] Chavez D. E., Hiskey M. A., J. Heterocycl. Chem., 1998, 35, 1329

[22] Xu K. Z., Zhao F. Q., Ren Y. H., Ma H. X., Song J. R., Hu R. Z., Acta Phys. Chim. Sin., 2009, 25, 309

[23] Chavez D. E., Hiskey M. A., Gilardi R. D., Org. Lett., 2004, 6, 2889

[24] Chavez D. E., Hiskey M. A., Naud D. L., Propellants Explos. Pyrotech., 2004, 29, 209

[25] Chavez D. E., Hiskey M. A., J. Energ. Mater., 1999, 17, 357

[26] Li X. T., Pang S. P., Yu Y. Z., Luo Y. J., Acta Chimica Sinica, 2007, 65, 971

[27] Kerth J., Lobbecke S., Propellants Explos. Pyrotech., 2002, 27, 111

[28] Cui Y., Zhang T. L., Zhang J. G., Yang L., Zhang J., Hu X. C., Struct. Chem., 2008, 19, 269

[29] Zhang J. G., Feng L. N., Zhang S. W., Zhang T. L., Zheng H. H., J. Mol. Model, 2008, 14, 403

[30] Cui Y., Zhang T. L., Zhang J. G., Yang L., Chin. J. Chem., 2008, 26, 2021

[31] Wu R. F., Zhang T. L., Qiao X. J., Yang L., Zhang J. G., Hu X. C., J. Coord. Chem., 2008, 61, 1437

[32] Cui Y., Zhang J. G., Zhang T. L., Yang L., Zhang J., Hu X. C., J. Hazard. Mater., 2008, 160, 45

[33] Yang L., Zhang J., Zhang T. L., Zhang J. G., Cui Y., J. Hazard. Mater., 2009, 164, 962

[34] Feng J. L., Zhang J. G., Zhang T. L., Cui Y., Acta Phys. Chim. Sin., 2010, 26, 2410

[35] Sheldrick G. M., SHELXS-97, Program for the Solution of Crystal Structure, University of Göttingen,Göttingen, 1997

[36] Sheldrick G. M., SHELXL-97, Program for the Refining of Crystal Structure, University of Göttingen,Göttingen, 1997

[37] Kissinger H. E., Anal. Chem., 1957, 29, 1702

[38] Ozawa T., Bull. Chem. Soc. Jpn., 1965, 38, 1881

[39] Doyle C. D., J. Appl. Polym. Sci., 1961, 5, 285

[40] Starink M. J., Thermochim. Acta, 1996, 288, 97

[41] Hu R. Z., Yang A. Q., Ling Y. J., Thermochim. Acta, 1988, 123, 135

[42] Liu Z. T., Lao Y. L., Initiating Explosive Experimental, Beijing Institute of Technology Press, Beijing, 1995, 238