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Quantum chemical studies on three novel 1,2,4-triazole N-oxides as potential insensitive high explosives

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Abstract

Three novel explosives were designed by introducing N-oxides into 1,2,4-triazole: 1-amino-3,5-dinitro-1,2,4-triazole-2 N-oxide (ADT2NO), 1-amino-2,5-dinitro-1,2,4-triazole-3 N-oxide (ADT3NO), and 1-amino-3,5-dinitro-1,2,4-triazole-4 N-oxide (ADT4NO). Their detonation performance and sensitivity were estimated by using density functional theory and compared with some famous explosives like 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) and 1-methyl–2,4,6-trinitrobenzene (TNT). All three designed molecules are more powerful than HMX and less sensitive than TNT, indicating that ADT2NO, ADT3NO, and ADT4NO have high detonation performance as HMX and low sensitivity as TNT, making them being very valuable and may be considered as the potential candidates of insensitive high explosives. Properly introducing N-oxides into the energetic triazole derivatives can generate some superior energetic compounds with both high explosive performance and reduced sensitivity.

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References

  1. Joo YH, Shreeve JM (2009) Angew Chem Int Ed 48: 564–567

  2. Stierstorfer J, Tarantik KR, Klapöke TM (2009) Chem Eur J 15:5775–5792

  3. Göbel M, Klapötke TM (2009) Adv Funct Mater 19: 347–367

  4. Joo YH, Shreeve JM (2010) Angew Chem Int Ed 49:7320–7323

  5. Thottempudi V, Gao HX, Shreeve JM (2011) J Am Chem Soc 133:6464–6471

  6. Politzer P, Lane P, Murray JS (2013) Cent Eur J Energ Mater 10: 37–52

  7. Wu Q, Zhu WH, Xiao HM (2013) J Chem Eng Data 58: 2748–2762

  8. Wu Q, Zhu WH, Xiao HM (2013) J Mol Model 19: 1853–1864

  9. Wu Q, Zhu WH, Xiao HM (2014) RSC Adv 4: 3789–3797

  10. Xue H, Gao HX, Twamley B, Shreeve JM (2007) Chem Mater 19: 1731–1739

  11. Tao GH, Twamley B, Shreeve JM (2009) J Mater Chem 19: 5850–5854

  12. Dippold AA, Klapötke TM (2012) Chem Eur J 18: 16742–16753

  13. Lin QH, Li YC, Li YY, Wang Z, Liu W, Qi C, Pang SP (2012) J Mater Chem 22: 666–674

  14. Zhang YQ, Parrish DA, Shreeve JM (2013) J Mater Chem A 1:585–593

  15. Meyer R, Köhler J, Homburg A (2007) Explosives. Wiley-VCH, Weinheim

    Book  Google Scholar 

  16. Tran TD, Pagoria PF, Hoffman DM, Cutting JL, Lee RS, Simpson RL (2002) The 33rd International Annual Conference of ICT. Karlsruhe, Germany

    Google Scholar 

  17. Hollins RA, Merwin LH, Nissan RA, Wilson WS, Gilardi R (1996) J Heterocyclic Chem 33: 895–904

  18. Politzer P, Lane P, Murray JS (2013) Struct Chem 24: 1965–1974

  19. Politzer P, Lane P, Murray JS (2014) Mol Phys 112: 719–725

  20. Demko ZP, Sharpless KB (2002) Angew Chem Int Ed 41: 2110–2113

  21. Wu Q, Zhu WH, Xiao HM (2013) J Mol Model 19: 2945–2954

  22. Atkins PW (1982) Physical chemistry. Oxford University Press, Oxford

    Google Scholar 

  23. Politzer P, Lane P, Murray JS (2011) Cent Eur J Energ Mater 8:39–52

  24. Politzer P, Murray JS, Grice ME, DeSalvo M, Miller E (1997) Mol Phys 91:923–928

  25. Bulat FA, Toro-Labbe A, Brinck T, Murray JS, Politzer P (2010) J Mol Model 16:1679–1691

  26. Jaidann M, Roy S, Abou-Rachid H, Lussier LS (2010) J Hazard Mater 176:165–173

  27. Wei T, Zhu WH, Zhang XW, Li YF, Xiao HM (2009) J Phys Chem A 113:9404–9412

  28. Kamlet MJ, Jacobs SJ (1968) J Chem Phys 48:23–35

  29. Politzer P, Martinez J, Murray JS, Concha MC, Toro-Labbé A (2009) Mol Phys 107:2095–2101

  30. Benson SW (1976) Thermochemical kinetic, 2nd edn. Wiley-Interscience, New York

    Google Scholar 

  31. Mills I, Cvitas T, Homann K, Kallay N, Kuchitsu K (1988) Quantities, units, and symbols in physical chemistry. Blackwell Scientific, Oxford

  32. Blanksby SJ, Ellison GB (2003) Accounts Chem Res 36:255–263

  33. Pospíšil M, Vávra P, Concha MC, Murray JS, Politzer P (2011) J Mol Model 17: 2569–2574

  34. Politzer P, Murray JS (2014) J Mol Model 20: 2223–2230

  35. Pospíšil M, Vávra P, Concha MC, Murray JS, Politzer P (2010) J Mol Model 16: 895–901

  36. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko, A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2009) Gaussian 09, Revision A. 01. Gaussian Inc, Wallingford

  37. Pepekin VI, Matyushin YN, Lebedev YA (1974) Russ Chem Bull 23: 1707–1710

  38. Dong HS, Zhou FF (1989) High energy detonators and correlative performances. Science, Beijing

  39. Trzciński WA, Cudziło S, Chyłek Z, Szymańczyk L (2008) J Hazard Mater 157: 605–612

  40. Rice BM, Hare JJ (2002) J Phys Chem A 106: 1770–1783

  41. Mayo SL, Olafson BD, Goddard WA (1990) J Phys Chem 94: 8897–8909

  42. Rice BM (2005) Adv Ser Phys Chem 16:335–367

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant No. 21273115) and A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions. Q. Wu would like to thank the Innovation Project for Postgraduates in Universities of Jiangsu Province (Grant No. CXZZ13_0199) for partial financial support.

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Authors and Affiliations

  1. Department of Chemistry, Institute for Computation in Molecular and Materials Science and, Nanjing University of Science and Technology, Nanjing, 210094, China

    Qiong Wu, Weihua Zhu & Heming Xiao

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  1. Qiong Wu
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  2. Weihua Zhu
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  3. Heming Xiao
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Correspondence to Weihua Zhu.

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Wu, Q., Zhu, W. & Xiao, H. Quantum chemical studies on three novel 1,2,4-triazole N-oxides as potential insensitive high explosives. J Mol Model 20, 2441 (2014). https://doi.org/10.1007/s00894-014-2441-z

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  • DOI: https://doi.org/10.1007/s00894-014-2441-z

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