Abstract
Density functional theory method was used to study the heats of formation (HOFs), electronic structure, energetic properties, and thermal stability for a series of 1,2,3,4-tetrazine-1,3-dioxide derivatives with different substituents and bridge groups. It is found that the groups –NO2, –C(NO2)3, and –N=N– play a very important role in increasing the HOFs of the derivatives. The effects of the substituents on the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels and HOMO–LUMO gaps are coupled to those of different substituents and bridges. The calculated detonation velocities and pressures indicate that the group –NO2, –NF2, –ONO2, –C(NO2)3, or –NH– is an effective structural unit for enhancing the detonation performance for the derivatives. An analysis of the bond dissociation energies for several relatively weak bonds indicates that incorporating the groups –NO2, –NF2, –ONO2, –C(NO2)3, and –N=N– into parent ring decreases their thermal stability. Considering the detonation performance and thermal stability, 18 compounds may be considered as the target compounds holding the greatest potential for synthesis and use as high-energy density compounds. Among them, the oxygen balances of four compounds are equal to zero. These results provide basic information for the molecular design of the novel high-energy compounds.
Similar content being viewed by others
References
Fried LE, Manaa MR, Pagoria PF, Simpson RL (2001) Annu Rev Mater Res 31:291–321
Qiu L, Xiao HM (2009) J Hazard Mater 164:329–336
Turker L, Varis S (2009) Polycycl Aromat Compd 29:228–266
Prabhakaran KV, Bhide NM, Kurian EM (1995) Thermochim Acta 249:249–258
Ravi P, Gore GM, Tewari SP, Sikder AK (2010) J Mol Struct Theochem 955:171–177
Qiu L, Zhu WH, Xiao JJ, Zhu W, Xiao HM, Huang H, Li JS (2007) J Phys Chem B 111:1559–1566
Ravi P, Gore GM, Tewari SP, Sikder AK (2011) Int J Quantum Chem 111:4352–4362
Talawar MB, Sivabalan R, Mukundan T, Muthurajan H, Sikder AK, Gandhe BR, Rao AS (2009) J Hazard Mater 161:589–607
Xu XJ, Zhu WH, Xiao HM (2007) J Phys Chem B 111:2090–2097
Zhang JJ, Gao HW, Wei T, Wang CJ (2010) Acta Phys Chim Sin 26:3337–3344
Wei T, Zhu WH, Zhang XW, Li YF, Xiao HM (2009) J Phys Chem A 113:9404–9412
Wei T, Zhu WH, Zhang JJ, Xiao HM (2010) J Hazard Mater 179:581–590
Tyurin AY, Churakov AM, Strelenko YA, Ratnikov MO, Tartakovsky VA (2006) Russ Chem Bull 55:1648–1653
Frumkin AE, Churakov AM, Strelenko YA, Tartakovsky VA (2006) Russ Chem Bull 55:1654–1658
Frumkin AE, Churakov AM, Strelenko YA, Tartakovsky VA (2000) Russ Chem Bull 49:482–486
Muthurajan H, Sivabalan R, Talawar MB, Anniyappan M, Venugopalan S (2006) J Hazard Mater 133:30–45
Zhu WX, Wong NB, Wang WZ, Zhou G, Tian A (2004) J Phys Chem A 108:97–106
Zhu WH, Zhang CC, Wei T, Xiao HM (2011) Struct Chem 22:149–159
Pan Y, Li JS, Cheng BB, Zhu WH, Xiao HM (2012) Comput Theor Chem 992:110–119
Wang F, Wang GX, Du HC, Zhang JJ, Gong XD (2011) J Phys Chem A 115:13858–13864
Xu XJ, Xiao HM, Ju XH, Gong XD, Zhu WH (2006) J Phys Chem A 110:5929–5933
Qiu L, Xiao HM, Gong XD, Ju XH, Zhu WH (2006) J Phys Chem A 110:3797–3807
Zeng Z, Gao H, Twamley B, Shreeve JM (2007) J Mater Chem 17:3819–3826
Thottempudi V, Gao HX, Shreeve JM (2011) J Am Chem Soc 133:6464–6471
Chavez D, Hiskey M (2009) J Energy Mater 17:357–377
Zhu WH, Zhang CC, Wei T, Xiao HM (2011) J Comput Chem 32:2298–2312
Zhang XW, Zhu WH, Xiao HM (2010) J Phys Chem A 114:603–612
Fan XW, Ju XH (2008) J Comput Chem 29:505–513
Curtiss LA, Raghavachari K, Redfern PC, Pople JA (1997) J Chem Phys 106:1063–1079
Wei T, Zhang JJ, Zhu WH, Zhang XW, Xiao HM (2010) J Mol Struct Theochem 956:55–60
Atkins PW (1982) Physical chemistry. Oxford University Press, Oxford
Politzer P, Lane P, Murray JS (2011) Cent Eur J Energy Mat 8:39–52
Politzer P, Murray JS (2011) Cent Eur J Energy Mat 8:209–220
Byrd EFC, Rice BM (2006) J Phys Chem A 110:1005–1013
Bulat FA, Toro-Labbe A, Brinck T, Murray JS, Politzer P (2010) J Mol Model 16:1679–1691
Jaidann M, Roy S, Abou-Rachid H, Lussier LS (2010) J Hazard Mater 176:165–173
Kamlet MJ, Jacobs SJ (1968) J Chem Phys 48:23–35
Politzer P, Martinez J, Murray JS, Concha MC, Toro-Labbé A (2009) Mol Phys 107:2095–2101
Benson SW (1976) Thermochemical kinetics. Wiley, New York
Mills I, Cvitas T, Homann K, Kallay N, Kuchitsu K (1988) Quantities, units, and symbols in physical chemistry. Blackwell Scientific Publications, Oxford
Blanksby SJ, Ellison GB (2003) Acc Chem Res 36:255–263
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
Dean JA (1999) Lange’s handbook of chemistry, 15th edn. McGraw-Hill Book Co., New York
Afeefy HY, Liebman JF, Stein SE (2000) Neutral thermochemical data. In: Linstrom PJ, Mallard WG (eds) NIST chemistry webbook, NIST standard reference database number 69. National Institute of Standards and Technology, Gaithersburg. http://webbook.nist.gov
Chung GS, Schmidt MW, Gordon MS (2000) J Phys Chem A 104:5647–5650
Acknowledgments
This work was supported by the National Natural Science Foundation of China (Grant No. 21273115) and the Fundamental Research Funds for the Central Universities (No. NUST2011YBXM08).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wu, Q., Pan, Y., Xia, X. et al. Theoretic design of 1,2,3,4-tetrazine-1,3-dioxide-based high-energy density compounds with oxygen balance close to zero. Struct Chem 24, 1579–1590 (2013). https://doi.org/10.1007/s11224-012-0190-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-012-0190-0