Hepta- and octanitrocubanes

Angewandte Chemie - International Edition

Volumn 39, Issue 2, 2000, Pages 401-404

  Zhang, Mao Xi ^a   Eaton, Philip E ^a   Gilardi, Richard ^b  

^a UNIVERSITY OF CHICAGO   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

Carbanions; Cubanes; Explosives; Nitrations; Nitro compounds

Indexed keywords

CUBANE DERIVATIVE; EXPLOSIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; NITRATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034677028     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000117)39:2<401::AID-ANIE401>3.0.CO;2-P     Document Type: Article

References (47)

1. a) The idea originated with E. E. Gilbert and J. Alster:
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4. Sec also: a) L. T. Eremenko, D. A. Nesterenko, Chem. Phys. Reports 1997, 16, 1675-1683:
5. b) A. M. Astakhov, R. S. Stepanov, A. Yu. Babushkin, Combustion, Explosion, and Shock Waves 1998, 34, 85-87.
6. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
7. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
8. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
9. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79-273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
10. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
11. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
12. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
13. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High-Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289- 299.
14. A variety of methods have been applied: a) A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, 1973; b) A. Immirzi, B. Perini, Acta Crystallogr. Sect. A 1977, 33, 216-218; c) H. H. Cady, Estimation of the Density of Organic Explosives from Their Structural Formulas, Report #LA-7760-MS, Los Alamos National Laboratory. Los Alamos, NM, 1979; d) D. A. Cichra, J. R. Holden, C. Dickinson, Estimation of "Normal" Densities of Organic Explosives from Empirical Atomic Volumes, Report #NSWC-TR-79- 273, Naval Surface Warfare Center (White Oak), Silver Spring, MD, 1980: c) J. R. Stine, Prediction of Crystal Densities of Organic Explosives by Group Additivity, Report #LA-8920, Los Alamos National Laboratory, Los Alamos, NM, 1981; f) J. Alster, S. Iyer, O. Sandus in Chemistry and Physics of Energetic Materials (Ed.: S. N. Bulusu), Kluwer, Dordrecht, 1990, chap. 28; g) J. R. Holden, Z. Du, H. L. Ammon, J. Comput. Chem. 1993, 13, 422-437; h) K. Jayasuriya, Computational Investigation of New Potential Explosive and Propellant Molecules, Fourteenth Annual Working Group Institute on High- Energy Density Materials, Kiamesha Lake, NY, 1995, pp. 2943-2963; i) J. S. Murray, T. Brinck, P. Politzer, Chem. Phys. 1996, 204, 289-299.
15. A variety of methods have been applied: a) L. C. Allen, Estimates for the Thermodynamic Stability of Cubane and its Nitro Derivatives, Eight Annual Working Group Institute on High-Energy Density Materials, Kiamesha Lake, NY, 1989, pp. 44-63; b) S. Bourasseau, J. Energ. Mater. 1990, 8, 378-391; c) P. Politzer, J. S. Murray, M. E. Grice in Decomposition, Combustion, and Detonation Chemistry of Energetic Materials (Eds.: T. B. Brill, T. P. Russell, W. C. Tao, R. B. Wardle), Materials Research Society, Pittsburgh, PA, 1996, 418, pp. 55-66; d) R. J. Spear, I. J. Dagley in Organic Energetic Compounds (Ed.: P. L. Marinkas), Nova, Commack, NY, 1996, chap. 2.
16. A variety of methods have been applied: a) L. C. Allen, Estimates for the Thermodynamic Stability of Cubane and its Nitro Derivatives, Eight Annual Working Group Institute on High-Energy Density Materials, Kiamesha Lake, NY, 1989, pp. 44-63; b) S. Bourasseau, J. Energ. Mater. 1990, 8, 378-391; c) P. Politzer, J. S. Murray, M. E. Grice in Decomposition, Combustion, and Detonation Chemistry of Energetic Materials (Eds.: T. B. Brill, T. P. Russell, W. C. Tao, R. B. Wardle), Materials Research Society, Pittsburgh, PA, 1996, 418, pp. 55-66; d) R. J. Spear, I. J. Dagley in Organic Energetic Compounds (Ed.: P. L. Marinkas), Nova, Commack, NY, 1996, chap. 2.
17. A variety of methods have been applied: a) L. C. Allen, Estimates for the Thermodynamic Stability of Cubane and its Nitro Derivatives, Eight Annual Working Group Institute on High-Energy Density Materials, Kiamesha Lake, NY, 1989, pp. 44-63; b) S. Bourasseau, J. Energ. Mater. 1990, 8, 378-391; c) P. Politzer, J. S. Murray, M. E. Grice in Decomposition, Combustion, and Detonation Chemistry of Energetic Materials (Eds.: T. B. Brill, T. P. Russell, W. C. Tao, R. B. Wardle), Materials Research Society, Pittsburgh, PA, 1996, 418, pp. 55-66; d) R. J. Spear, I. J. Dagley in Organic Energetic Compounds (Ed.: P. L. Marinkas), Nova, Commack, NY, 1996, chap. 2.
18. A variety of methods have been applied: a) L. C. Allen, Estimates for the Thermodynamic Stability of Cubane and its Nitro Derivatives, Eight Annual Working Group Institute on High-Energy Density Materials, Kiamesha Lake, NY, 1989, pp. 44-63; b) S. Bourasseau, J. Energ. Mater. 1990, 8, 378-391; c) P. Politzer, J. S. Murray, M. E. Grice in Decomposition, Combustion, and Detonation Chemistry of Energetic Materials (Eds.: T. B. Brill, T. P. Russell, W. C. Tao, R. B. Wardle), Materials Research Society, Pittsburgh, PA, 1996, 418, pp. 55-66; d) R. J. Spear, I. J. Dagley in Organic Energetic Compounds (Ed.: P. L. Marinkas), Nova, Commack, NY, 1996, chap. 2.
19. R. L. Simpson, P.A. Urtiew, D. L. Ornellas, G. L. Moody. K. J. Scribner, D. M. Hoffman, Propellants Explos. Pyrotech. 1997, 22, 249-255.
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31. [7b] δ = 90.1, 87.5, 83.3, 62.2;
32. 3 from two separate crystals); 2243 data measured to a 20 max. of 115 ; R = 0.0471, wR2 = 0.1141 for all 1881 unique reflections.
33. 3);
34. 3; 2345 data measured to a 20 max. of 113.5 ; R = 0.0579, wR2 = 0.1339 for all 1115 unique reflections.
35. R. S. Rowland, R. Taylor, J. Phys. Chem. 1996, 100, 7384-7391.
36. 3CN): δ = 88.3 (3C), 85.9 (1C), 82.9 (3C), 36.7 (C-1);
37. 3; 1175 data measured to a 2θ max. of 115 ; R = 0.0412, wR2 = 0.1077 for all 1079 unique reflections.
38. See a) W. Hanefeld, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1990, Vol 16/2a, pp. 950-979; b) J. M. Kauffman, J. Green, M.S. Cohen, M. M. Fein, E. L. Cottrill, J. Am. Chem. Soc. 1964, 86, 4210- 4211; c) E. Müller, H. Metzger, Chem. Ber. 1956, 89, 396-406.
39. See a) W. Hanefeld, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1990, Vol 16/2a, pp. 950-979; b) J. M. Kauffman, J. Green, M.S. Cohen, M. M. Fein, E. L. Cottrill, J. Am. Chem. Soc. 1964, 86, 4210-4211; c) E. Müller, H. Metzger, Chem. Ber. 1956, 89, 396-406.
40. See a) W. Hanefeld, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1990, Vol 16/2a, pp. 950-979; b) J. M. Kauffman, J. Green, M.S. Cohen, M. M. Fein, E. L. Cottrill, J. Am. Chem. Soc. 1964, 86, 4210- 4211; c) E. Müller, H. Metzger, Chem. Ber. 1956, 89, 396-406.
41. 3; 2241 data measured to a 2θ max. of 116 ; R = 0.0389, wR2 = 0.0962 for all 1076 unique reflections.
42. a) H. Ammon, private communication, see ref. [3g];
43. b) Using: W. R. Busing, WMIN - A Computer Program to Model Molecules and Crystals in Terms of Potential Energy Functions. Report #ORNL-5747, Oak Ridge National Laboratory, Oak Ridge, TN, 1981;
44. c) using: D. J. Willock, S. L. Price, M. Leslie, C. R. A. Catlow, J. Comput. Chem. 1995, 16, 628-647.
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46. [19) M. D. Coburn, C.B. Storm, D.W. Moore, T. U. Archibald, Magn. Reson. Chem. 1990, 28, 16-20.
47. 2 differences, and uses all data; that is, weak data are not considered "unobserved", and are included in the R-factors reported. Crystallographic data (excluding structural factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-127760 (4), -127761 (5), -127762 (6), and -127763 (7). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk)