Structural characteristics and reactivity relationships of nitroaromatic and nitramine explosives - A review of our computational chemistry and spectroscopic research

International Journal of Molecular Sciences

Volumn 8, Issue 12, 2007, Pages 1234-1264

  Qasim, Mohammad M ^a   Moore, Brett ^a   Taylor, Lyssa ^a   Honea, Patricia ^c   Gorb, Leonid ^a,b   Leszczynski, Jerzy ^a,d  

^a US ARMY ENGINEER RESEARCH AND DEVELOPMENT CENTER   (United States)

^b SpecPro Contractor ^*

^c UNIVERSITY OF MISSISSIPPI MEDICAL CENTER   (United States)

^d JACKSON STATE UNIVERSITY   (United States)

Author keywords

Activity relationships; degradation mechanisms; Nitramine explosives; structural; Nitroaromatic

Indexed keywords

2,4,6,8 TETRANITRO 1,3,5,7 TETRAAZA CUBANE; 2,4,6,8,10,12 HEXANITROHEXA AZOISOWURTZITANE; AMINE; AROMATIC NITRO COMPOUND; CYCLONITE; NITRAMINE; OCTAHYDRO 1,3,5,7 TETRANITRO 1,3,5,7 TETRAZOCINE; OCTONITROCUBANE; PICRIC ACID; TRINITROBENZENESULFONIC ACID; TRINITROTOLUENE; UNCLASSIFIED DRUG;

CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DEGRADATION; HYDROLYSIS; INFRARED SPECTROSCOPY; LIGHT ABSORPTION; MATHEMATICAL COMPUTING; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 38149027030     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/i8121234     Document Type: Review

References (109)

1. Brannon, J.; Deliman, P.; Gerald, J.; Ruiz, C.; Price, C.; Hayes, C.; Yost, S.; Qasim, M. Conceptual Model and Processes Descriptor Formulations for Fate and Transport of UXO. Tech IRRP-99-1, USACE, WES: Vicksburg, 1999.
2. Chilkapati, A.; Ginn, A.; Szecsody, J. An Analysis of Complex Reaction Networks in Groundwater Modeling. Water Resources Res. 1988, 34(7), 1767-1780.
3. Hawari, J. ; Deschamps, S. ; Beaulieu, C. ; Paquet, L.; Halasz, A. Photodegradation of CL-20: insights into the mechanisms of initial reactions and environmental fate. Elsevier Water Research 2004, 38, 4055-4064.
4. Stahl, J.; Aust, S. Biodegradation of 2,4,6-Trinitrotoluene by the White Rot Fungus Phanerochaete Chrysosporium. In Biodegradation of Nitroaromatic Compounds; Spain, J., Ed.; Plenum Press: New York, 1994; Environmental Science Research, Vol. 49, pp. 117-133.
5. Szecsody, J.; Girvin, D.; Devary, B.; Campbell, J.; Fredrickson, H.; Crocker, F.; Qasim, M.; Riley, R.; Gamerdinger, A.; Lemond, L.. Factors Effecting the Fate and Transport of CL-20 in the Vadose Zone and Groundwater: Progress Report for 2003. End of Year Tech. Report, 12/2003.
6. Szecsody, J. et al. Sorption & oxic degradation of the explosive CL-20 during transport in subsurface sediments. Chemosphere 2004, 56, 593-610.
7. Ainsworth, C.; Harvey, S.; Szecsody, J. Relationships between the leachability characteristics of unique energetic compounds and soil properties, Rep. 91PP1800.; US Army Med. Res., 1993.
8. Ownby, D.; Belden, J.; Lotufo, G.; Lydy, M. Accumulation of trinitrotoluene (TNT) in aquatic organisms: Part I - Bioconcentration and distribution in channel catfish (Ictalurus punctatus). Chemosphere 2005, 58, 1153-1159.
9. Ownby, D.; Belden, J.; Lotufo, G.; Lydy, M. Accumulation of trinitrotoluene (TNT) in aquatic organisms: Part II - Bioconcentration in aquatic invertebrates and potential for trophic transfer to channel catfish (Ictalurus punctatus). Chemosphere 2005, 58, 1161-1168.
10. Weissmahr, K.; Haderlein, S.; Schwarzenbach, R. In Situ Spectroscopic Investigations of Adsorption Mechanisms of Nitroaromatic Compounds at Clay Minerals. Environ. Sci. Technol. 1997, 31,240-247.
11. Dodard, S.; Renoux, A.; Hawari, J.; Ampleman, G.; Thiboutot, S.; Sunahara, G. Ecotoxicity Characterization of Dinitrotoluenes and some of their reduced metabolites. Chemosphere 1999, 38, 2071-2079.
12. Etnier, E. Water quality criteria for hexahydro-1,3,5-trinitro-1,3,5- triazine (RDX). Regul Toxico. Pharm. 1989, 9, 147-57.
13. Honeycutt, M.; Jarvis, A.; McFairland, V. Cytotoxicity and Mutagenicity of 2,4,6-Trinitrotoluene and Its Metabolites. Exotoxicology and Environmental Safety 1996, 35, 282-287.
14. Lachance, B.; Robidoux, P.; Hawari, J.; Ampleman, G.; Thiboutot, S.; Sunahara, G. Cytotoxic and genotoxic effects of energetic Compounds on bacterial and mammalian cells in vitro. Genetic Toxicol. and Environ Mutagenesis, Mutation Res. 1999, 444, 25-39.
15. Robidoux, P.; Hawari, J.; Thiboutot, S. Acute and chronic toxicity of the new explosive CL-20 to the earthworm (eisenia Andrei) exposed to amended natural soils. Environ. Toxico. Chem. 1999, 23, 1026.
16. Sciences International, Inc. Toxicological Profile for 2,4,6-Trinitrotoluene; U.S. Department of Health and Human Services, June 1995.
17. Bajpai, R.; Kim, J.; Qasim, M. Bioremediaion. In Ency. of Agriculture, Food, and Biological Engineering. CRC Press: Boca Raton, 2003, 108-118.
18. Adam, M.; Comfort, S.; Morley, M.; Snow, D. Remediating RDX-Contaminated Ground Water with Permanganate: Laboratory Investigation for the Pantex Perched Aquifer. J. of Environmental Quality 2004, 33, 2165-2173.
19. Balakrishnan, V.; Halasz, A.; Hawari, J. Alkaline Hydrolysis of the Cyclic Nitramine Explosives, RDX, HMX and CL-20: New Insights into Degradation Pathways Obtained by the Observation of Novel Intermediates. Environ. Sci. Tech. 2003, 37, 1838-1843.
20. Balakrishnan, V.; Monteil-Rivera, F.; Halasz, A.; Corbeanu, A.; Hawari, J. Decomposition of the Polycyclic Nitramine Explosive, CL-20 by Fe(0). Environ. Sci. Technol. 2004, 38, 6861-6866.
21. Bernasconi, C. Kinetic and Spectral Study of Some Reactions of 2,4,6-Trinitrotoluene in Basic Solution. I. Deprotonation and Janovsky Complex Formation. J. Org. Chem. 1971, 36, 1671-679.
22. Brannon, J.; Qasim, M.; Price, C.; Yost, S. Photodegradation of TNT in Water & Sediment/Water Systems. WES Rep., Env. Eng. Div.-USAE, WES, 1998.
23. Bonin, P.; Bejan, D.; Schutt, L.; Hawari, J.; Bunce, N. Electrochemical Reduction of Hexahydro-1,3,5-trinitro-1,3,5-triazine in Aqueous Solutions. Environ. Sci. Technol. 2004, 38 (5), 1595-99.
24. Emmrich, M. Kinetics of the Alkaline Hydrolysis of Important Co-contaminants of 2,4,6-Trinitrotoluene in Highly Contaminated Soils. Environ. Sci. Technol. 2001, 35, 874-877.
25. Emmrich, M. Kinetics of the Alkaline Hydrolysis of 2,4,6-Trinitrotoluene in Aqueous Solution and Highly Contaminated Soils. Environ. Sci. Technol. 1999, 33, 3802-3805.
26. Hansen, L.; Larson, S.; Fell, D.; Qasim, M.; Cullinane, M. Based-Catalyzed Transformations of Explosive Compounds in Soil & Water. In Proceedings of the USACE Env. Dev. Workshop, Portland, OR, 2001.
27. Heilmann, H.; Wiesmann, U.; Stenstrom, M. Kinetics of Alkaline Hydrolysis of High Explosives RDX and HMX in Aqueous and Adsorbed to Activated Carbon. Environ. Sci. Technol. 1996, 30, 1485-1485.
28. Heilmann, H.; Stenstrom, M. Hesselmann, R.; Wiesmann, U. Kinetics of the aqueous alkaline homogeneous hydrolysis of high explosive 1,3,5,7-tetraaza 1,3,5,7-tetranitrocyclooctane (HMX). Water Sci. Technol. 1994, 30, 53-61.
29. Li, Z.; Shea, P.; Comfort, S. Destruction of 2,4,6-Trinitrotoluene by Fenton Oxidation. J. Env. Quality. 1997, 26, 480-487.
30. Agrawal, A.; Tratnyek, P. Reduction of nitroaromatic compounds by zero-valent iron metal. Environ. Sci. Technol. 1966, 30, 153-160.
31. Bier, E.; Singh, Z.; Li, S.; Comfort, S.; Shea, P. Remediating hexahydro-1,3,5-trinitro-1,3,5-triazine-contaminated water and soil by Fenton oxidation. Env. Toxicol. Chem. 1999, 18, 1078-1084.
32. Christensen, H. et al. Reactions of Hydroxyl Radicals with Hydrogen Peroxide at Ambient and Elevated Temperatures. J. Phys. Chem. 1982, 86 (9), 1588-1590
33. Hundal, L.; Singh, J.; Bier, E.; Shea, P.; Comfort, S.; Powers, W. Removal of TNT and RDX from water and soil using iron metal. Environ. Pollut. 1997, 97, 55-64.
34. Singh, J.; Comfort, S.; Shea, P. Remediating RDX-contaminated water and soil using zero-valent iron. J. Environ Qual. 1998, 27, 1240-1245.
35. Melius, C. Thermochemical modeling. I. Application to decomposition of energetic materials. Chemistry and Physics of Energetic Materials. Bulusu, S. N. Ed. Kluwer: Dordrecht, Netherlands, 1990, 21-49.
36. Schmelling, D.; Gray, K.; Kamat, P. Role of Reduction in the Photocatalytic Degradation of TNT. Environ. Sci. Technol. 1996, 30, 2547-2555.
37. Thorn, K.; Thorne, P.; Cox, L. Alkaline Hydrolysis/Polymerization of 2,4,6-Trinitrotoluene: Characterization of Products by 13C and 15N NMR. Environ. Sci. Technol.2004, 38, 2224-2231.
38. Wight, C.; Botcher, T. Thermal decomposition of solid RDX begins with N-N bond scission. J. Am. Chem. Soc. 1992, 114, 8030-8304.
39. Zappi, M.; Miller, J.; Qasim, M. Development of Chemical Oxidation Processes for Use in Remediating Conaminated Department of Defense Sites. In Special Publ. on Military Res. Act.; Am. Soc. of Agronomy, 1996.
40. Zhao, X.; Hintsa, E.; Lee, Y. Infrared multiphoton dissociation of RDX in a molecular beam. J. Chem. Phys. 1988, 88, 801-810.
41. Bajpai, R.; Qasim, M.; Hansen, L.; Popovic, M.; Paco, J. Chemical and Biological Reactions of TNT & RDX. In Proceedings of the International Congress of Chemistry & Process Engineering, Chisa, Czech Republic, Aug 25-29, 2002; pp. 15.
42. Bajpai, R.; Parekh, D.; Herrmann, S.; Popovic, M.; Paca, J.; Qasim, M. A kinetic model of aqueous-phase alkali hydrolysis of 2,4,6-trinitrotoluene. J. Haz. Mat. 2004, 106B, 55-66.
43. Karasch, C.; Popovic, M.; Qasim, M.; Bajpai, R. Alkali Hydrolysis of Trinitrotoluene. Biochem. & Biotech. 2002, 14, 1176-1186.
44. Michalkova, A.; Rasulev, B.; Qasim, M.; Gorb, L.; Furey, J.; Fredrickson, H.; Leszczynski, J. Explosives: Modeling their interactions with Clay Minerals and Toxicity. AHPCRC Bulletin, 55458-1459; Army High Performance Computer Research Center: Minneapolis, MN, 2006.
45. Bhushan, B.; Halasz, A.; Spain, J.; Hawari, J. Initial Reaction(s) to Biotransformation of CL-20 is Catalyzed by Salicylate 1-Monooxygenase from Pseudomonas sp. Strain ATCC 29352. Appl. & Environ. Microbiology. 2004, 7, 4040-4047.
46. Coleman, N.; Nelson, D.; Duxbury, T. Aerobic biodegradation of the hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) as a nitrogen source by a Rhodococcus sp., strain DN22. Soil Biol. Biochem. 1998, 30, 1159-1166.
47. Fournier, D.; Halasz, A.; Spain, J.; Spanggord, R.; Bottaro, J.; Hawari, J. Biodegradation of the Hexadydro-1,3,5-Trinitro-1,3,5-Triazine Ring Cleavage Producing 4-Nitro-2,4-Diazabutanol by Phanerochaete chrysosporium. Appl. & Environ. Microbiology, 2004, 70(2), 1123-1128.
48. Hawari, J. Biodegradation of RDX and HMX: from Basic Research to Field Application; In Biodegradation of Nitroaromatic Compounds and Explosives; Spain, J, Hughes, J., Knackmuss, H., Eds.; Lewis Pub: Boca Raton, FL, 2000; pp. 278-310.
49. Krumholz, L.; Li, J.; Clarkson, W.; Wilber, G.; Suflita, J. Transformations of TNT and related aminotoluenes in groundwater aquifer slurries under different electron-accepting conditions. J. Indus. Microbiology & Biotech. 1997, 18(2-3), 161-169.
50. th Int. Conf. on Adv. Oxida.Tech. for Water & Air Remediation, Albuquerque, NM, May, 1999.
51. Spain, J. In Biodegradation of Nitroaromatic Compounds and Explosives. Spain, J., Hughes, J., Knackmuss, H.-J., Eds.; CRC Press: Boca Raton, FL, 2000; Chapter 1.
52. Binks, P.; Nicklin, S.; Bruce, N. Degradation of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) by Stenotrophomonas maltophilia PBI. Appl. Environ. Microbiol. 1995, 61, 1318-1322.
53. Wackett, L. Evolution of enzymes for the metabolism of new chemical inputs in the environment. J. Biol. Chem. 2004, 279, 41259-41262.
54. Politzer, P.; Murray, J.; Seminario, J.; Lane, P.; Grice, M.; Concha, M. Computational characterization of energetic materials. J. Molecular Structure (Theochem.). 2001, 573, 1-10.
55. Qasim, M.; Fredrickson, H.; McGrath, C.; Bajpai, R. Modes of Degradation of Cyclic Nitramines: An Approximation Methods Comparison of the Relationships Between the Structures and Reactivities of CL-20, ONC, TNTAC, and RDX; Oral presentation; 11th Conference on Current Trends in Computational Chemistry, Jackson, MS, 2002.
56. Qasim, M.; Fredrickson, H.; Furey, J.; McGrath, C. Theoretical Predictions of Chemical Degradation Reaction Mechanisms of Cyclic (RDX, HMX) and Cage Cyclic (CL-20, ONC, TNTAC) Nitramines as Related to Their Molecular Structures with Experimental Verification Using CL-20 as Model; SERDP/ESTCP: Washington, DC, 2003.
57. Qasim, M.; Furey, J.; Fredrickson, H.; Szecsody, J.; McGrath, C.; Bajpai, R. Semiempirical Predictions of Chemical Degradation Reaction Mechanisms of CL-20 as Related to Molecular Structure. J. Structural Chemistry. 2004, 15 (5), 493-499.
58. Qasim, M.; Fredrickson, H.; Honea, P.; Leszczynski, J.; Okovytyy, S.; Szecsody, J.; Kholod, Y. Prediction of CL-20 Chemical Degradation Pathways, Theoretical and Experimental Evidence for Dependence on Competing Modes of Reaction. SAR and QSAR in Env. Res. 2005, 16 (5), 495-515.
59. Qasim, M.; Fredrickson, H.; McGrath, C.; Furey, J.; Bajpai, R. Theoretical Predictions of Chemical Degradation Reaction Mechanisms of RDX and Other Cyclic Nitramines Derived from Their Molecular Structures. SAR/QSAR in Environ. Res. 2005, 16 (3), 203-218.
60. Qasim, M.; Honea, P.; Gorb, L.; Leszczynski, J. Molecular Structure Determines Chemical Reactivities and, Thus, Transformation Pathways. In Proceedings of the 25th Army Science Conference, Orlando, FL, 2006.
61. Isayev, O.; Rasulev, B.; Gorb, L.; Leszczynski, L. Structure-Toxicity Relationships of Nitroaromatic Compounds. J. Mol. Diver. 2006, 10 (2), 233-245.
62. Stewart, J. MOPAC 2000 Manual; Fujitsu Limited, 1999.
63. Okovytyy, S.; Kholod, Y.; Qasim, M.; Frederickson, H.; Leszczynski, J. The Mechanism of Unimolecular Decomposition of CL-20 (2,4,6,8,10,12 Hexanitro-2,4,6,8,10,12-Hexaazaisowurtzitane). A Computational DFT Study. Technical Report for Army High Performance Computing Research Center, Report Number 2004-177.
64. Kholod, Y.; Okovytyy, S.; Qasim, M.; Honea, P.; Furey, J.; Fredrickson, H.; Leszczynski, J. A DFT Study of the IR and UV/VIS Spectra of CL-20 Degradation Products. In Proceedings of the 5th Southern Schl. on Computaional Chemistry, Jackson, MS, Apr 8-9, 2005.
65. Okovytyy, S.; Kholod, Y.; Qasim, M.; Frederickson, H.; Leszczynski, J. The Mechanism of Unimolecular Decomposition of CL-20 (2,4,6,8,10,12 Hexanitro-2,4,6,8,10,12Hexaazaisowurtzitane). A Computational DFT Study. J. Phys. Chem. 2005, 109, 2964-2970.
66. Kuz'min, V.; Muratov, E.; Artemenko, A.; Gorb, L.; Qasim, M.; Leszczynski, J. QSAR analysis and virtual screening of nitroaromatic toxicity in vivo. J. Mol. Mod. 2005, 11, 457-467 (and references cited therein).
67. Rieger, P.; Knckmuss, H. Basic knowledge and perspectives on biodegradation of 2,4,6-trinitrotoluene and related nitroaromatic compounds in contaminated soil. Biodegradation of Nitroaromatic Compounds. Spain, J. C. , Ed. Plenum Press: New York. 1995, 1-18.
68. Haderlein, S.; Hofstetter, T.; Schwarzenbach, R. Surface Chemistry of Nitroaromatic Compounds. In Biodegradation of Nitroaromatic Compounds and Explosives; Spain, J.C., Hughes, J.B., Knackmuss, H.J, Eds.; CRC Press: Boca Raton, FL, 2000.
69. Davis, E.; Boopathy, R.; Manning, J. Use of trinitrobenzene as a nitrogen source by Pseudomonas vesicularis isolated from soil. Curr. Microbiology. 1997, 34 (3), 192-197.
70. Boopathy, R.; Manning, J. Surfactant-Enhanced Bioremediation of Soil Contaminated with 2,4,6-Trinitrotoluene in Soil Slurry Reactors. Water Environment Research. 2001, 71, 19-24.
71. Meharg, A.; Dennis, G.; Calmey, J. Biotransformation of 2,4,6-trinitrotoluene (TNT) by ecomycorrhizal basidiomycetes. Chemosphere 1997, 35 (3), 513-521.
72. Hawari, J.; Halasz, A.; Sheremata, T.; Beaudet, S.; Groom, C.; Paquet, L.; Rhofir, L.; Ampleman, G.; Thiboutot, S. Characterization of metabolites during biodegradation of hexahydro-1,3,5-trinitro-1,3,5 triazine (RDX) with municipal anaerobic sludge. Appl. Environ. Microbiol. 2000, 66, 2652-2657.
73. McCormick, N.; Cornell, J.; Kaplan, A. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5 triazine. Appl. Environ. Microbiol. 1981, 42, 817-823.
74. McCormick, N.; Cornell, J.; Kaplan, A. The anerobic biotransformation of RDX, HMX and their acetylated derivatives. Technical Report for the US Army Natick Res. & Dev. Center, Natick, MA, AD Rep. A149464 (TR85-008), 1985.
75. Rajan, J.; Valli, K.; Perkins, R.E.; Sariaslani, F.; Barns, S.; Reysenbach, A.; Rehm, S.; Ehringer, M.; Pace, N. Mineralization of 2,4,6-Trinitrophenol (Picric acid); Characterization and Phylogenic Identification of Microbial Strains. J. Indus. Microbiol. 1996, 16, 319-324.
76. Vorbeck, C.; Lenke, H.; Fischer, P.; Knackmuss, H. Identification of a Hydride-Meisenheimer Complex as a Metabolite of 2,4,6-Trinitrotoluene by a Mycobacterium Strain. J. Bacteriology 1994, 176 (3), 932-934.
77. Major, M. Conversion of TNT to Biodegradable Compounds by Dissolution in Alkaline Solutions. Submitted, U.S. Army Center for Health Promotion and Preventive Medicine, Aberdeen Proving Ground, MD. Army Technical Manual TM9-1300-214, Ref.1, 1998.
78. Carper, W.; Davis, E.; Extine, M. Molecular Structure of 2,4,6-Trinitrotoluene. J. Phys. Chem. 1982, 86, 459-459.
79. Carey, F. Organic Chemistry; McGraw-Hill: New York, 1994; pp. 418-424, 448-461.
80. Ege, S. Organic Chemistry; Heath and Co.: Lexington, MA, 1989, pp. 555+, 967.
81. Fessenden, R.; Fessenden, J. Organic Chemistry; Willard Grant Press: Boston, MA, 1982.
82. th edition of the March book was edited by M. Smith, 2001)
83. McMurray, J. Organic Chemistry; Brooks/Cole Pub.: Pacific Grove, CA, 1988; pp. 548-565.
84. Morrison, R.; Boyd, R. Organic Chemistry, 5th Ed.; Allyn and Bacon: Boston, MA, 1987.
85. Streitwieser, A.; Heathcock, C.; Kosower, E. Introduction to Organic Chemistry; Macmillan: New York, 1987; pp. 780-781.
86. th Army Science Conference, Orlando, FL, Nov, 2006.
87. Qasim, M.; Hansen, L.; Bajpai, R. Minimized Energy Calculations of TNT and Its Possible Transformation Products under Competing Conditions. Oral presentation, 7th Conference on Current Trends in Computaional Chemistry, Vicksburg, MS, Nov, 1998.
88. Qasim, M.; Honea, P.; Fredrickson, H. Comparative Study of Reaction Mechanisms of TNT and Selected Analogues Using Free Radical Generators and Alkaline Hydrolysis. Oral presentation, 2nd DoD Sustainable Ranges Initiative, San Antonio, TX, Aug 22-25, 2005.
89. Chakraborty, D.; Muller, R.; Dasgupta, S.; Goddard, W., III. The Mechanism for Unimolecular Decomposition of RDX (1,3,5-Trinitro-1,3,5-triazine), an ab initio study. J. Phys. Chem A. 2000, 104, 2261-2272.
90. Qasim, M.; Hansen, L. Two Pathways generated through approximation methods: a mechanistic study of RDX Degradation. Oral presentation, 9th Conference on Current Trends in Computational Chemistry, Vicksburg, MS, Nov 4, 2000.
91. Sewell, T.; Thompson, D. Classical dynamics study of unimolecular dissociation of hexahydro-1,3,5-trinitro-1,3,5-triazine. J. Phys. Chem. 1991, 95, 6228-6242.
92. Rice, B.; Sorescu, D. Assessing a Generalized CHNO Intermolecular Potential through ab Initio Crystal Structure Prediction. J. Phys. Chem. B 2004, 108, 17730-17739.
93. Monteil-Rivera, F.; Paquet, L.; Deschamps, S.; Balakrishnan, V.; Beaulieu, C.; Hawari, J. Physico-chemical measurements of CL-20 for environmental applications comparison with RDX and HMX. Elsevier, J. of Chromatog. A 2004, 1025, 125-132.
94. Lewis, J.; Glaesemann, K.; VanOpdorp, K.; Voth, G. Ab Initio Calculations of Reactive Pathways for α-Octahydro-1,3,5,7-tetranitro-1,3,5,7- tetrazocine (α-HMX). J. Phys. Chem. A 2000, 104, 11384-11386.
95. Lewis, J.; Sewell, T.; Evans, R.; Voth, G. Electronic Structure Calculation of the Structures and Energetics of the Three Pure Polymorphic Forms of Crystalline HMX. J. Phys. Chem. B 2000, 104, 1009-1013.
96. Sorescu, D.; Rice, B.; Thompson, D. Molecular Packing & NPT-Molecular Dynamics Investigation of the Transferability of the RDX Intermolecular Potential to 2,4,6,8,10,12-Hexanitrohexaazaisowurtzitane. J. Phys. Chem. B 1998, 102, 948-52.
97. Nielsen, A.; Chafin, S.; Christian, D.; Moore, M.; Nadler, R.; Nissan, D. Synthesis of polyazapolycylic caged Polynitramines. Tetrahedron 1998, 54, 11793-11812.
98. Nielsen, A. Nitrocarbons. In Organic Nitro Chemistry Series; VCH Publishers: New York, 1995.
99. Chan, M.; Boggs, T. Advanced CL-20 Based propellant Formulated by China Lake Team, 02/07/2001.
100. Research Team, Naval Weapons Center, China Lake, CA. Technical reports regarding CL-20, separate booklets: Parts 1-8, 1990-1994.
101. Honea, P.; Qasim, M.; Fredrickson, H.; Furey, J.; Okovytyy, S.; Kholod, Y.; Leszcynski, J. Stopped-Flow and UV-VIS Spectrophotometric Studies of the Transformation of CL-20. Poster presented at the 13th Conference on Current Trends in Computational Chemistry, Nov 12-13, 2004.
102. Qasim, M.; Simplified Concepts in Spectroscopy and Photochemistry, USAE WES Tech. Rep. IRRP-97- 4/1997.
103. Clark, G.; Hawley, G. The Encyclopedia of Chemistry, 2nd Ed.; Reinhold Publ. Corp.: New York, 1966.
104. Dean, J. Lange's Handbook of Chemistry, 14th Ed.; McGraw-Hill: New York, 1992.
105. Lide, D., Ed. Handbook of Chemistry and Physics, 76th Ed.; CRC Press: Boca Raton, FL, 1996.
106. Nielson, A. Nitrocarbons Organic Nitro Chemistry Series. VCH Publishers: New Jersey, 1995.
107. Bard, A., Dekker, M., Eds.; Encyclopedia of Electrochemistry of the Elements; Marcel Dekker Inc, New York, 1976; Volume 8.
108. Patai, S. The Chemistry of the Carbon Nitrogen Double Bond; Interscience Pub.: London, UK, 1970.
109. Kholod, Y.; Okovytyy, S.; Kuramshina, G.; Qasim, M.; Gorb, L.; Leszczynski, J. An Analysis of stable forms of CL-20: A DFT study of conformational transitions, infrared and Raman spectra. J. Mol. Struct. 2007, 843, 14-25.