Theoretical studies on polynitro-1,3-bishomopentaprismanes as potential high energy density compounds

Journal of Hazardous Materials

Volumn 166, Issue 2-3, 2009, Pages 931-938

  Qiu, Limei ^a,b   Gong, Xuedong ^a   Zheng, Jian ^b   Xiao, Heming ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Technology Corporation   (China)

Author keywords

Bond dissociation energy; Density; Density functional theory; Detonation properties; Heat of formation

Indexed keywords

BOND DISSOCIATION ENERGY; DENSITY; DETONATION PROPERTIES; DETONATION VELOCITIES; GEOMETRIC STRUCTURES; GROUP ADDITIVITY RULES; HEAT OF FORMATION; HEATS OF FORMATIONS; HIGH ENERGY DENSITIES; JACOBS EQUATIONS; NITRO GROUPS; PYROLYSIS PROCESS; SINGLE BONDS; SPACE DISTANCES; THEORETICAL STUDIES; THERMAL STABILITIES;

CHEMICAL BONDS; DETONATION; DISSOCIATION; THERMOCHEMISTRY; THERMODYNAMIC STABILITY;

DENSITY FUNCTIONAL THEORY;

CHEMICAL COMPOUND; POLYNITRO 1,3 BISHOMOPENTAPRISMANE; UNCLASSIFIED DRUG;

CHEMICAL BONDING; DENSITY; NITROGEN DIOXIDE; ORGANIC NITROGEN COMPOUND; THEORETICAL STUDY;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENERGY; GEOMETRY; PYROLYSIS; THEORETICAL STUDY; THERMOSTABILITY;

BENZENE DERIVATIVES; EXPLOSIVE AGENTS; MODELS, THEORETICAL; NITRO COMPOUNDS; POLYCYCLIC COMPOUNDS; THERMODYNAMICS;

EID: 67349127595     PISSN: 03043894     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2008.11.099     Document Type: Article

References (49)

1. 8: a structure analogous to pentalene, and other high-energy density minima. J. Phys. Chem. 99 (1995) 2324-2328
2. Korkin A.A., and Bartlett R.J. Theoretical prediction of 2,4,6-trinitro 1,3,5-triazine (TNTA). A new, powerful, high-energy density material?. J. Am. Chem. Soc. 118 (1996) 12244-12245
3. Eaton P.E., Gilardi R.L., and Zhang M.X. Polynitrocubanes: advanced high-density high-energy materials. Adv. Mater. 12 (2000) 1143-1148
4. Eaton P.E., Ravi Shankar B.K., Price G.D., Pluth J.J., Gilbert E.E., Alster J., and Sanders O. Synthesis of 1,4-dinitrocubane. J. Org. Chem. 49 (1984) 185-186
5. Zhang J., and Xiao H.M. Computational studies on the infrared vibrational spectra, thermodynamic properties, detonation properties and pyrolysis mechanism of octanitrocubane. J. Chem. Phys. 116 (2002) 10674-10683
6. Xu X.J., Xiao H.M., Gong X.D., Ju X.H., and Chen Z.X. Theoretical studies on the vibrational spectra, thermodynamic properties, detonation properties and pyrolysis mechanisms for polynitroadamantanes. J. Phys. Chem. A 109 (2005) 11268-11274
7. Xu X.J., Xiao H.M., Ju X.H., Gong X.D., and Zhu W.H. Computational studies on polynitrohexaazaadmantanes as potential high energy density materials (HEDMs). J. Phys. Chem. A 110 (2006) 5929-5933
8. de Vries L., and Winstein S. Neighboring carbon and hydrogen. XXXIX. Complex rearrangements of bridged ions. rearrangement leading to the bird-cage hydrocarbon. J. Am. Chem. Soc. 82 (1960) 5363-5376
9. Liebman J.F., and Greenberg A. A survey of strained organic molecules. Chem. Rev. 76 (1976) 311-365
10. 5,9]dodecane (1,3-bishomopentaprismane). J. Org. Chem. 51 (1986) 1897-1900
11. Soloway S.B., Damiana A.M., Sims J.W., Bluestone H., and Lidov R.E. Skeletal rearrangements in reactions of isodrin and endrin. J. Am. Chem. Soc. 82 (1960) 5377-5385
12. Carter P., Howe R., and Winstein S. Preparation and solvolytic behavior of a bridgehead birdcage alcohol. J. Am. Chem. Soc. 87 (1965) 914-915
13. Mehta G., and Reddy R.K. Dioxa-1,3-bishomopentaprismane: synthesis and transformations. J. Org. Chem. 52 (1987) 460-462
14. 8,11]undecane-8-carboxylic acid (homopentaprismane-8-carboxylic acid). J. Org. Chem. 54 (1989) 3226-3229
15. Paquette L.A., and Fischer J.W. Synthesis and X-ray crystal structure analysis of a vicinally dinitro-substituted bishomopentaprismane. J. Org. Chem. 50 (1985) 2524-2527
16. 9,12]dodecane-5,11-dione and its conversion to di-, tri-, and tetranitro-1,3-bishomopentaprismanes. Chem. Ber. 119 (1986) 3782-3800
17. Shen C.C., and Paquette L.A. Impact of a basal nitro group on the density characteristics of select [4]peristylane derivatives. J. Org. Chem. 54 (1989) 3324-3328
18. Qiu L., Xiao H.M., Gong X.D., Ju X.H., and Zhu W.H. Theoretical studies on the structures, thermodynamic properties, detonation properties, and pyrolysis mechanisms of spiro nitramines. J. Phys. Chem. A 110 (2006) 3797-3807
19. Qiu L., Xiao H.M., Ju X.H., and Gong X.D. Theoretical study on the structures and properties of cyclic nitramines: tetranitrotetraazadecalin (TNAD) and its isomers. Int. J. Quant. Chem. 105 (2005) 48-56
20. Wang G.X., Xiao H.M., Xu X.J., and Ju X.H. Detonation velocities and pressures, and their relationships with electric spark sensitivities for nitramines. Propellants Explos. Pyrotech. 31 (2006) 102-109
21. Qiu L., Xiao H.M., Gong X.D., and Ju X.H. Theoretical studies on the thermodynamic properties and detonation properties of bicyclic nitramines: TNAD isomers. Chin. J. Struct. Chem. 25 (2006) 1309-1320
22. 2 groups. Int. J. Quant. Chem. 106 (2006) 1561-1568
23. Wang G.X., Xiao H.M., Ju X.H., and Gong X.D. Calculation of detonation velocity, pressure, and electric sensitivity of nitro arenes based on quantum chemistry. Propellants Explos. Pyrotech. 31 (2006) 361-368
24. Wang G.X., Xiao H.M., Ju X.H., and Gong X.D. Theoretical studies on densities. detonation velocities and pressures and electric spark sensitivities of energetic materials. Acta Chim. Sin. 65 (2007) 517-524
25. Xiao H.M., Xu X.J., and Qiu L. Theoretical Design of High Energy Density Materials (2008), Science Press, Beijing
26. Frisch M.J., Trucks G.W., Schlegel H.B., et al. Gaussian 03, Revision B.03 (2003), Gaussian, Inc., Pittsburgh, PA
27. Becke A.D. Density-founctional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98 (1993) 5648-5653
28. Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37 (1988) 785-789
29. Hariharan P.C., and Pople J.A. Influence of polarization functions on MO hydrogenation energies. Theor. Chim. Acta 28 (1973) 213-222
30. Scott A.P., and Radom L. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Moiler-Plesset, quadratic configuration interaction, density functional theory and semiempirical scale factors. J. Phys. Chem. 100 (1996) 16502-16513
31. Curtiss L.A., Raghavachari K., and Redfern P.C. Assessment of complete basis set methods for calculation of enthalpies of formation. J. Chem. Phys. 108 (1998) 692-697
32. D.R. Lide, "Standard Thermodynamic Properties of Chemical Substances", in CRC Handbook of Chemistry and Physics, Internet Version 2005, , CRC Press, Boca Raton, FL, 2005.
33. Qiu L.M., Gong X.D., Zheng J., and Xiao H.M. Investigation on heats of formation for energetic compounds based on atomization reactions. Chin. J. Energ. Mater. 6 (2008) 647-650
34. Kamlet M.J., and Jacobs S.J. Chemistry of detonations. I. A simple method for calculating detonation properties of CHNO explosives. J. Chem. Phys. 48 (1968) 23-35
35. Zhang X.H., and Yun Z.H. Explosive Chemistry (1989), National Defence Industry Press, Beijing
36. J.R. Stine, Los Alamos National Laboratory's Report, New Mexico, 1981.
37. Ammon H.L. New atom/functional group volume additivity data bases for the calculation of the crystal densities of C, H, N, O, F, S, P, Cl and Br-containing compounds. Struct. Chem. 12 (2001) 205-212
38. Sorescu D.C., Rice B.M., and Thompson D.L. Intermolecular potential for the hexahydro-1,3,5-trinitro-1,3,5-s-triazine crystal (RDX): a crystal packing, monte carlo, and molecular dynamics study. J. Phys. Chem. B 101 (1997) 798-808
39. Karfunkel H.R., and Gdanitz R.J. Ab initio prediction of possible crystal structures for general organic molecules. J. Comp. Chem. 13 (1992) 1171-1183
40. Qiu L., Xiao H.M., Gong X.D., Ju X.H., and Zhu W.H. Crystal density predictions for nitramines based on quantum chemistry. J. Hazard. Mater. 141 (2007) 280-288
41. 2 scission in some nitroaromatic molecules. J. Mol. Struct.: Theochem. 583 (2002) 69-72
42. Wijeratne N.R., and Wenthold P.G. Thermochemical studies of benzoylnitrene radical anion: the N-H bond dissociation energy in benzamide in the gas phase. J. Phys. Chem. A 111 (2007) 10712-10716
43. Zhu X.Q., Hao W.F., Tang H., Wang C.H., and Cheng J.P. Determination of N-NO bond dissociation energies of N-methyl-N-nitrosobenzenesulfonamides in mechanism analyses on NO transfer. J. Am. Chem. Soc. 127 (2005) 2678-2696
44. Owens F.J. Calculation of energy barriers for bond rupture in some energetic molecules. J. Mol. Struct.: Theochem. 370 (1996) 11-16
45. 2 bonds: applications to impact sensitivities. J. Mol. Struct.: Theochem. 376 (1996) 419-424
46. Harris N.J., and Lammertsma K. 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 (1997) 6583-6589
47. 4. J. Phys. Chem. A 109 (2005) 8011-8015
48. Zhang J., Xiao H.M., and Gong X.D. Theoretical studies on heats of formation for polynitrocubanes using the density functional theory B3LYP methods and semiempirical MO methods. J. Phys. Org. Chem. 14 (2001) 583-588
49. Engler E.M., Andose J.D., and Schleyer P.R. Critical evaluation of molecular mechanics. J. Am. Chem. Soc. 95 (1973) 8005-8025