A theoretical study on 1,5-diazido-3-nitrazapentane (DANP) and 1,7-diazido-2,4,6-trinitrazaheptane (DATNH): Molecular and crystal structures, thermodynamic and detonation properties, and pyrolysis mechanism

Journal of Molecular Modeling

Volumn 19, Issue 12, 2013, Pages 5367-5376

  Yang, Junqing ^a   Wang, Fang ^a   Zhang, Jianying ^a   Wang, Guixiang ^a   Gong, Xuedong ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Azido nitramine; Density functional theory; Detonation performance; Plasticizer; Pyrolysis mechanism

Indexed keywords

1,5 DIAZIDO 3 NITRAZAPENTANE; 1,7 DIAZIDO 2,4,6 TRINITRAZAHEPTANE; CYCLONITE; PLASTICIZER; PROPELLANT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DETONATION; MOLECULAR MECHANICS; PRESSURE; PRIORITY JOURNAL; PROTON TRANSPORT; PYROLYSIS; THEORETICAL STUDY; THERMODYNAMICS; THERMOSTABILITY; VELOCITY;

EID: 84890857086     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-013-2014-6     Document Type: Article

References (48)

1. Provatas A (2000) Energetic polymers and plasticisers for explosive formulations - a review of recent advances. DSTO-TR-0966.
2. Flanagan JE, Wilson ER, Frankel MB (1991) 1, 5-diazido-3-nitrazapentane and method of preparation thereof. US: 5013856
3. Ji YP, Lan Y, Li PR, Wang W, Ding F, Liu YJ (2008) Synthesis and characterization of 1,5-diazido-3-nitrazapentane (DIANP). Chin J Explos Propell 31:44-46
4. Zhang ZZ, Wang BZ, Shi ZC, Ji YP, Liu Q, Zhu CH (2003) Synthesis and properties of 1,7-Diazido-2,4, 6-trinitro-2,4,6-triazoheptane. Chin J Explos Propell 26:3-5
5. Klapötke TM, Krumm B, Steemann FX (2009) Preparation, characterization, and sensitivity data of some azidomethyl nitramines. Propell Explos Pyrotech 34:13-23
6. Wang JL, Ji YP, Gao FL, Guo W, Ren ST (2011) Experimental measurement of safety parameters of DIANP. Chin J Energ Mater 19:693-696
7. Oyumi Y, Rheingold A, Brill T (1987) Thermal decomposition of energetic materials. 19. Unusual condensed-phase and thermolysis properties of a mixed azidomethyl nitramine: 1,7-diazido-2,4,6-trinitro-2,4,6-triazaheptane. J Phys Chem 91:920-925
8. Wang W, Ding F, Liang Y, Ji YP, Liu WX (2010) Preparation and characterization of DIANP certified reference material. Chin J Explos Propell 33:52-55
9. Brill T, Karpowicz R, Haller T, Rheingold A (1984) A structural and fourier-transform infrared-spectroscopic characterization of the thermal decomposition of 1-(azidomethyl)-3,5,7-trinitro-1,3,5,7-tetraazacyclooctane. J Phys Chem 88:4138-4143
10. Dang ZM, Zhao FQ (2000) Thermal decomposition characteristics of low signature propellant containing 1,7-diazido-2,4,6-trinitrazaptane. Xi'an JiaoTong University XueBao 34:88-92
11. 2NH), hydrogen cyanide (HCN), and hydrogen isocyanide (HNC). J Phys Chem A 115:250-264
12. Chakraborty D, Muller RP, Dasgupta S, Goddard WA (2000) The mechanism for unimolecular decomposition of RDX (1,3,5-trinitro-1,3,5-triazine), an ab initio study. J Phys Chem A 104:2261-2272
13. Li JS, Xiao HM, Gong XD, Dong HS (1999) Theoretical study on the mechanism, thermodynamics and kinetics of 2-azido-1,3,5-trinitrobenzene thermolysis. Explos Shock Waves 19:1-5
14. Frisch MJ, Trucks GW, Schlegel HB, Suzerain GE, Robb MA, Cheeseman JrJR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov B, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision B.05, Gaussian: Wallingford.
15. Materials Studio 4.4 (2008) Accelrys, San Diego, CA
16. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785-789
17. Becke AD (1992) Density-functional thermochemistry. II. The effect of the Perdew-Wang generalized-gradient correlation correction. J Chem Phys 97:9173-9177
18. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648-5652
19. Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 28:213-222
20. Xu XJ, Xiao HM, Gong XD, Ju XH, Chen ZX (2005) Theoretical studies on the vibrational spectra, thermodynamic properties, detonation properties, and pyrolysis mechanisms for polynitroadamantanes. J Phys Chem A 109:11268-11274
21. Gong XD, Xiao HM (2001) Studies on the molecular structures, vibrational spectra and thermodynamic properties of organic nitrates using density functional theory and ab initio methods. J Mol Struct THEOCHEM 572:213-221
22. Qiu L, Xiao HM, Ju XH, Gong XD (2005) Theoretical study of the structures and properties of cyclic nitramines: tetranitrotetraazadecalin (TNAD) and its isomers. Int J Quantum Chem 105:48-56
23. Mayo SL, Olafson BD, Goddard WA (1990) Dreiding: a generic force field for molecular simulations. J Phys Chem 94:8897-8909
24. Hill TL (1960) An introduction to statistical thermodynamics. Courier Dover, New York
25. Scott AP, Radom L (1996) Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem 100:16502-16513
26. Wong MW (1996) Vibrational frequency prediction using density functional theory. Chem Phys Letters 256:391-399
27. Haynes WM, Lide DR, Bruno TJ (2012) CRC handbook of chemistry and physics. Taylor and Francis (CRC), Boca Raton
28. Atkins PW, Clugston MJ (1982) Principles of physical chemistry. Oxford University Press, Oxford
29. Rice BM, Pai SV, Hare J (1999) Predicting heats of formation of energetic materials using quantum mechanical calculations. Combust Flame 118:445-458
30. Politzer P, Ma Y, Lane P, Concha MC (2005) Computational prediction of standard gas, liquid, and solid-phase heats of formation and heats of vaporization and sublimation. Int J Quantum Chem 105:341-347
31. Gong XD (2007) Potden v.2.0. Nanjing University of Science and Technology: Nanjing.
32. Kamlet MJ, Jacobs SJ (1968) Chemistry of detonations. I. A simple method for calculating detonation properties of C-H-N-O explosives. J Chem Phys 48:23-35
33. Politzer P, Murray JS (2011) Some perspectives on estimating detonation properties of C, H, N, O compounds. Central Eur J Energ Mater 8:209-220
34. Wang GX, Gong XD, Xiao HM (2009) Theoretical investigation on density, detonation properties, and pyrolysis mechanism of nitro derivatives of benzene and aminobenzenes. Int J Quantum Chem 109:1522-1530
35. Zhang JY, Du HC, Wang F, Gong XD, Huang YS (2011) DFT studies on a high energy density cage compound 4-trinitroethyl-2, 6, 8, 10,12- pentanitrohezaazaisowurtzitane. J Phys Chem A 115:6617-6621
36. Wang F, Du HC, Zhang JY, Gong XD (2011) Computational studies on the crystal structure, thermodynamic properties, detonation performance, and pyrolysis mechanism of 2,4,6,8-tetranitro-1,3,5,7-tetraazacubane as a novel high energy density material. J Phys Chem A 115:11788-11795
37. Politzer P, Murray J, Grice M, Sjoberg P, Olah G, Squire D (1991) Chemistry of energetic materials. Academic, San Diego
38. 2 groups. J Comput Chem 32:943-952
39. Wang GX, Gong XD, Du HC, Liu Y, Xiao HM (2011) Theoretical prediction of properties of aliphatic polynitrates. J Phys Chem A 115:795-804
40. Kamlet M, Adolph H (1979) The relationship of impact sensitivity with structure of organic high explosives. II. Polynitroaromatic explosives. Propell Explos Pyrotech 4:30-34
41. Xu XJ, Zhu WH, Xiao HM (2008) Molecular packing prediction and periodic calculations on three polynitroadamantanes as potential high energy density compounds. Chin J Chem 26:602-606
42. Ghule V, Jadhav P, Patil R, Radhakrishnan S, Soman T (2009) Quantum-chemical studies on hexaazaisowurtzitanes. J Phys Chem A 114:498-503
43. Li YF, Fan XW, Wang ZY, Ju XH (2009) A density functional study of substituted pyrazole derivatives. J Mol Struct: THEOCHEM 896:96-102
44. Ju XH, Wang ZY, Yan XF, Xiao HM (2007) Density functional theory studies on dioxygen difluoride and other fluorine/oxygen binary compounds: availability and shortcoming. J Mol Struct: THEOCHEM 804:95-100
45. Harris NJ, Lammertsma K (1997) Ab initio density functional computations of conformations and bond dissociation energies for hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine. J Am Chem Soc 119:6583-6589
46. Xiao HM, Xu XJ, Qiu L (2008) Theoretical design of high energy density materials. Science, Beijing
47. Flanagan JE, Grant LE, Thompson WW, Woolery D (1985) The stable pyrolysis products of the monomers. Air Force Rocket Propulsion Laboratory, Junction, CA
48. Talawar M, Sivabalan R, Mukundan T, Muthurajan H, Sikder A, Gandhe B, Rao AS (2009) Environmentally compatible next generation green energetic materials (GEMs). J Hazard Mater 161:589-607