A G4MP2 and G4 theoretical study into the thermochemical properties of explosophore substituted tetrahedranes and cubanes

Propellants, Explosives, Pyrotechnics

Volumn 36, Issue 5, 2011, Pages 410-415

  Rayne, Sierra ^a   Forest, Kaya ^b  

^a Ecologica Research   (Canada)

^b OKANAGAN UNIVERSITY COLLEGE   (Canada)

Author keywords

Cubanes; Explosophoric Substituents; High Energy Materials; Tetrahedranes; Theoretical Study

Indexed keywords

CUBANES; EXPLOSOPHORIC SUBSTITUENTS; HIGH ENERGY MATERIALS; TETRAHEDRANES; THEORETICAL STUDY;

ACETYLENE; GASES; HIGH ENERGY PHYSICS; MERCURY (METAL); MERCURY COMPOUNDS; QUANTUM CHEMISTRY;

ENTHALPY;

EID: 80054812384     PISSN: 07213115     EISSN: 15214087     Source Type: Journal    
DOI: 10.1002/prep.201000165     Document Type: Article

References (56)

1. M. W. Schmidt, M. S. Gordon, J. A. Boatz, Cubic Fuels?, Int. J. Quantum Chem. 2000, 76, 434.
2. M. B. Talawar, R. Sivabalan, M. Anniyappan, G. M. Gore, S. N. Asthana, B. R. Gandhe, Emerging Trends in Advanced High Energy Materials, Comb. Expl. Shock Waves 2007, 43, 62.
3. E. G. Lewars, Modeling Marvels, Springer, New York 2008.
4. D.M. Badgujar, M.B. Talawar, S.N. Asthana, P.P. Mahulikar, Advances in Science and Technology of Modern Energetic Materials: An Overview, J. Haz. Mater. 2008, 151, 289.
5. R.M. Minyaev, V.I. Minkin, Nonclassical Carbon: From Theory to Experiment, Russ. J. Gen. Chem. 2008, 78, 732.
6. S. Alvarez, J. Echeverria, New Perspectives on Polyhedral Molecules and their Crystal Structures, J. Phys. Org. Chem. 2010, 23, 1080.
7. S. Rayne, K. Forest, Structures, Enthalpies of Formation, and Ionization Energies For the Parent and Binary mixed Carbon, Silicon, Nitrogen, and Phosphorus Cubane Derivatives: A G4MP2Theoretical Study, Nat. Prec. 2010, doi:10.1038/npre.2010.5154.1.
8. S. Rayne, K. Forest, Gas-Phase Enthalpies of Formation, Acidities, and Strain Energies of the [m,n]Polyprismanes (m≥2; n=3-8; m-16): A CBS-Q//B3, G4MP2, and G4 Theoretical Study, Theor. Chem. Acct. 2010, 127, 697.
9. P. E. Eaton, T. W. Cole, Cubane, J. Am. Chem. Soc. 1964, 86, 3157.
10. L. A. Paquette, R. J. Ternansky, D. W. Balogh, G. Kentgen, Total Synthesis of Dodecahedrane, J. Am. Chem. Soc. 1983, 105, 5446.
11. L.A. Paquette, Dodecahedrane: The Chemical Transliteration of Platos Universe, Proc. Natl. Acad. Sci. USA 1982, 79, 4495.
12. G. Maier, S. Pfriem, U. Schafer, R. Matusch, Tetra-tert- butyltetrahedrane, Angew. Chem. Int. Ed. Engl. 1978, 17, 520.
13. G. Maier, J. Neudert, O. Wolf, D. Pappusch, A. Sekiguchi, M. Tanaka, T. Matsuo, Tetrakis(trimethylsilyl)tetrahedrane, J. Am. Chem. Soc. 2002, 124, 13819.
14. A. Nemirowski, H.P. Reisenauer, P.R. Schreiner, Tetrahedrane: Dossier of an Unknown, Chem. Eur. J. 2006, 12, 7411.
15. P.E. Eaton, M.X. Zhang, R. Gilardi, N. Gelber, S. Iyer, R. Surapaneni, Octanitrocubane: A New Nitrocarbon, Propellants Explos. Pyrotech. 2002, 27, 1.
16. R. Gilardi, R.J. Butcher, The Structure of Nitrocubane: The Last in the Series of Nitrocubanes, J. Chem. Crystallogr. 2003, 33, 281.
17. M. Zhang, P. E. Eaton, R. Gilardi, Hepta- and Octanitrocubanes, Angew. Chem. Int. Ed. 2000, 39, 401.
18. P.E. Eaton, R. Gilardi, M. Zhang, Polynitrocubanes: Advanced High-Density, High-Energy Materials, Adv. Mater. 2000, 12, 1143.
19. P. E. Eaton, B. K. R. Shankar, G. D. Price, J. J. Pluth, E. E. Gilbert, J. Alster, O. Sandus, Synthesis of 1,4-Dinitrocubane, J. Org. Chem. 1984, 49, 185.
20. P.E. Eaton, Y. Xiong, R. Gilardi, Systematic Substitution on the Cubane Nucleus. Synthesis and Properties of 1,3,5-Trinitrocubane and 1,3,5,7-Tetranitrocubane, J. Am. Chem. Soc. 1993, 115, 10195.
21. K. A. Lukin, J. Li, P. E. Eaton, N. Kanomata, J. Hain, E. Punzalan, R. Gilardi, Synthesis and Chemistry of 1,3,5,7-Tetranitrocubane including Measurement of its Acidity, Formation of o-Nitro Anions, and the First Preparations of Pentanitrocubane and Hexanitrocubane, J. Am. Chem. Soc. 1997, 119, 9591.
22. 3,6]heptane-2-carboxylic Acid, Acta Crystallogr., Sect. E 2002, 58, 862.
23. x (x=1-8)
24. J. Haz. Mater. 2009, 164, 1595.
25. X. W. Fan, X. H. Ju, Q. Y. Xia, H. M. Xiao, Strain Energies of Cubane Derivatives with Different Substituent Groups, J. Haz. Mater. 2008, 151, 255.
26. x (x=1-8), J. Haz. Mater. 2009, 164, 1552.
27. X. H. Ju, Y. M. Li, H. M. Xiao, Theoretical Studies on the Heats of Formation and the Interactions Among the Difluoroamino Groups in Polydifluoroaminocubanes, J. Phys. Chem. A 2005, 109, 934.
28. X. H. Ju, Z. Y. Wang, Theoretical Study on Thermodynamic and Detonation Properties of Polynitrocubanes, Propellants Explos. Pyrotech. 2009, 34, 106.
29. 4n (n=0-4), Compd. Mater. Sci. 2009, 46, 849.
30. F. J. Owens, Molecular Orbital Calculation of Decomposition Pathways of Nitrocubanes and Nitroazacubanes, THEOCHEM 1999, 460, 137.
31. J. Li, An Evaluation of Nitro Derivatives of Cubane using Ab Initio and Density Functional Theories, Theor. Chem. Acc. 2009, 122, 101.
32. J. Kortus, M.R. Pederson, S.L. Richardson, Density Functional-based Prediction of the Electronic, Structural, and Vibrational Properties of the Energetic Molecule: Octanitrocubane, Chem. Phys. Lett. 2000, 322, 224.
33. J. A. Bumpus, A. Lewis, C. Stotts, C. J. Cramer, Characterization of High Explosives and other Energetic Compounds by Computational Chemistry and Molecular Modeling, J. Chem. Educ. 2007, 84, 329.
34. D. A. Hrovat, W. T. Borden, P. E. Eaton, B. Kahr, A Computational Study of the Interactions Among the Nitro Groups in Octanitrocubane, J. Am. Chem. Soc. 2001, 123, 1289.
35. X. H. Ju, H. M. Xiao, Q. Y. Xia, A Periodic DFT Approach to Octanitrocubane Crystal, Chem. Phys. Lett. 2003, 382, 12.
36. P. Politzer, J. M. Seminario, Computational Analysis of the Structures, Bond Properties, and, Electrostatic Potentials of some Nitrotetrahedranes and Nitroazatetrahedranes, J. Phys. Chem. 1989, 93, 4742.
37. M. Grodzicki, J. M. Seminario, P. Politzer, Conformation-dependent Effects of the Nitro Group upon some Strained Tertiary Ci-C Bonds, J. Phys. Chem. 1990, 94, 624.
38. G. Zhou, J. L. Zhang, N. B. Wong, A. Tian, Computational Studies on a Kind of Novel Energetic Materials Tetrahedrane and Nitro Derivatives, THEOCHEM 2004, 668, 189.
39. L. A. Curtiss, P. C. Redfern, K. Raghavachari, Gaussian-4 Theory using Reduced Order Perturbation Theory, J. Chem. Phys. 2007, 127, 124105.
40. L. A. Curtiss, P. C. Redfern, K. Raghavachari, Gaussian-4 Theory, 16405 J. Chem. Phys. 2007, 126, 84108.
41. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, etal., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT 2009.
42. R. Allouche, Gabedit: A Graphical User Interface for Computational Chemistry Softwares, J. Comput. Chem. 2011, 32, 174.
43. W. M. F. Fabian, Accurate Thermochemistry From Quantum Chemical Calculations?, Monatsh. Chem. 2008, 139, 309.
44. M. Saeys, M.F. Reyniers, G.B. Marin, V. vanSpeybroeck, M. Waroquier, Ab Initio Calculations for Hydrocarbons: Enthalpy of Formation, Transition State Geometry, and Activation Energy for Radical Reactions, J. Phys. Chem. A 2003, 107, 9147.
45. V. vanSpeybroeck, R. Gani, R. J. Meier, The Calculation of Thermodynamic Properties of Molecules, Chem. Soc. Rev. 2010, 39, 1764.
46. S. Rayne, K. Forest, Estimated Gas-Phase Standard State Enthalpies of Formation for Organic Compounds using the Gaussian-4 (G4) and W1BD Theoretical Methods, J. Chem. Eng. Data 2010, 55, 5359.
47. 2 Chlorofluorocarbons and Hydrochlorofluorocarbons, THEOCHEM 2010, 953, 47.
48. 2n (n=1-6) isomers, THEOCHEM 2010, 948, 111.
49. S. Rayne, K. Forest, Gas Phase Isomerization Enthalpies of Organic Compounds: A Semiempirical, Density Functional Theory, and Ab initio Post-Hartree-Fock Theoretical Study, THEOCHEM 2010, 948, 102.
50. J. D. Cox, D. D. Wagman, V. A. Medvedev, CODATA Key Values For Thermodynamics, Hemisphere, New York 1984.
51. J. Akhavan, The Chemistry of Explosives, Royal Society of Chemistry, Cambridge 2004.
52. J. Abdelmalik, D. W. Ball, DFT Calculations on Nitrodiborane Compounds as New Potential High Energy Materials, J. Mol. Model. 2010, 6, 915.
53. R. L. Simpson, P. A. Urtiew, D. L. Ornellas, G. L. Moody, K. J. Scribner, D. M. Hoffman, CL-20 Performance Exceeds that of HMX and its Sensitivity is Moderate, Propellants Explos. Pyrotech. 1997, 22, 249.
54. M. X. Zhang, P. E. Eaton, R. Gilardi, Hepta- and Octanitrocubanes, Angew. Chem. Int. Ed. 2000, 39, 401.
55. K.Y. Mathews, D.W. Ball, New Potential High Energy Materials: High-level Calculations on the Properties of Aminonitromethanes, THEOCHEM 2008, 868, 78.
56. K.Y. Mathews, D.W. Ball, Calculated Thermochemistry of Aminonitroacetylene: A New High-Energy Material?, J. Phys. Chem. Lett. 2009, 113, 4855.