Molecular Design of New Nitramine Explosive: 1,3,5,7-Tetraaza-1,2,3,5, 6,7-hexahydros-indacene Derivatives

REFERENCES

• Bushuyev , O. S. , Brown , P. , Maiti , A. , Gee , R. H. , Peterson , G. R. , Weeks , B. L. and Hope-Weeks , L. J. 2012 . Ionic Polymers as a New Structural Motif for High-Energy-Density Materials . J. Amer. Chem. Soc. , 134 : 1422 – 5 .
   PubMed Web of Science ®Google Scholar
• Gutsev , G. L. , Weatherford , C. A. , Johnson , L. E. and Jena , P. 2012 . Structure and Properties of the Aluminum Borates Al(BO2)n and Al(BO2)n-, (n = 1–4) . J. Comput. Chem. , 33 : 416 – 24 .
   PubMed Web of Science ®Google Scholar
• Li , X. H. , Fu , Z. M. and Zhang , X. Z. 2012 . Computational DFT Studies on a Series of Toluene Derivatives as Potential High Energy Density Compounds . Struct. Chem. , 23 : 515 – 24 .
   Web of Science ®Google Scholar
• Scott , A. M. , Petrova , T. , Odbadrakh , K. , Nicholson , D. M. , Fuentes-Cabrera , M. , Lewis , J. P. , Hill , F. C. and Leszczynski , J. 2012 . Molecular Simulations of Adsorption of RDX and TATP on IRMOF-1(Be) . J. Mol. Model. , 18 : 3363 – 78 .
   PubMed Web of Science ®Google Scholar
• Liu , H. , Wang , F. , Wang , G. X. and Gong , X. D. 2012 . Theoretical Investigations on Structure, Density, Detonation Properties, and Sensitivity of the Derivatives of PYX . J. Comput. Chem. , 33 : 1790 – 6 .
   PubMed Web of Science ®Google Scholar
• Murray , J. S. , Concha , M. C. and Politzer , P. 2009 . Links between Surface Electrostatic Potentials of Energetic Molecules, Impact Sensitivities and C‒NO2/N‒NO2 Bond Dissociation Energies . Mol. Phys. , 107 : 89 – 97 .
   Web of Science ®Google Scholar
• Pospisil , M. , Vavra , P. , Concha , M. C. , Murray , J. S. and Politzer , P. 2011 . Sensitivity and the Available Free Space per Molecule in the Unit Cell . J. Mol. Model. , 17 : 2569 – 74 .
   PubMed Web of Science ®Google Scholar
• Kohno , Y. , Hiyoshi , R. I. , Yamaguchi , Y. , Matsumoto , S. , Koseki , A. , Takahashi , O. , Yamasaki , K. and Ueda , K. 2009 . Molecular Dynamics Studies of the Structural Change in 1,3-Diamino-2,4,6-trinitrobenzene (DATB) in the Crystalline State under High Pressure . J. Phys. Chem. A , 113 : 2551 – 60 .
   PubMed Web of Science ®Google Scholar
• Ghule , V. D. , Sarangapani , R. , Jadhav , P. M. and Tewari , S. P. 2011 . Computational Design and Structure-property Relationship Studies on Heptazines . J. Mol. Model. , 17 : 2927 – 37 .
   PubMed Web of Science ®Google Scholar
• Zhao , G. Z. and Lu , M. 2012 . A Theoretical Investigation on the Densities and Detonation Properties of Polynitrotetraazabenzimidazoles . CR. Chim. , 15 : 808 – 814 .
   Web of Science ®Google Scholar
• Boddu , V. M. , Viswanath , D. S. , Ghosh , T. K. and Damavarapu , R. 2010 . 2,4,6-Triamino-1,3,5- trinitrobenzene (TATB) and TATB-based Formulations-A review . J. Hazard. Mater. , 181 : 1 – 8 .
   PubMed Web of Science ®Google Scholar
• An , C. W. , Wang , J. Y. , Xu , W. Z. and Li , F. S. 2010 . Preparation and Properties of HMX Coated with a Composite of TNT/Energetic Material . Propelllants Explos. Pyrotech. , 35 : 365 – 72 .
   Web of Science ®Google Scholar
• Manaa , M. R. , Reed , E. J. , Fried , L. E. and Goldman , N. 2009 . Nitrogen-Rich Heterocycles as Reactivity Retardants in Shocked Insensitive Explosives . J. Amer. Chem. Soc. , 131 : 5483 – 7 .
   PubMed Web of Science ®Google Scholar
• Carboni , R. A. and Castle , J. E. 1962 . Dibenze-1,3a,4,6a-tetrazapentalene: A New Heteroatomic System . J. Amer. Chem. Soc. , 84 : 2453 – 4 .
   Web of Science ®Google Scholar
• Nair , U. R. , Gore , G. M. , Sivabalan , R. , Pawar , S. J. , Asthana , S. N. and Venugopalan , S. 2007 . Preparation and Thermal Studies on Tetranitrodibenzo Tetraazapentalene (TACOT): A Thermally Stable High Explosive . J. Hazard. Mater. , 143 : 500 – 5 .
   PubMed Web of Science ®Google Scholar
• Sikder , A. K. and Nirmala , S. 2004 . A Review of Advanced High Performance, Insensitive and Thermally Stable Energetic Materials Emerging for Military and Space Applications . J. Hazard. Mater. , 112 : 1 – 15 .
   PubMed Web of Science ®Google Scholar
• Bellamy , A. J. 2010 . Synthesis of Hexanitrostilbene (HNS) using a Kenics Static Mixer . Org. Process. Res. Dev. , 14 : 632 – 9 .
   Web of Science ®Google Scholar
• Wang , G. X. , Shi , C. H. , Gong , X. D. and Xiao , H. M. 2009 . Theoretical Investigation on Structures, Densities, Detonation Properties, and the Pyrolysis Mechanism of the Derivatives of HNS . J. Phys. Chem. A , 113 : 1318 – 26 .
   PubMed Web of Science ®Google Scholar
• Zhao , G. Z. and Lu , M. 2012 . Theoretical Studies on High Energetic Density Nitramine Explosives Containing Pyridine . Sci. China Chem. , 55 : 1903 – 9 .
   Web of Science ®Google Scholar
• Witko , E. M. and Korter , T. M. 2012 . Terahertz Spectroscopy of the Explosive Taggant 2,3-Dimethyl-2,3-Dinitrobutane . J. Phys. Chem. A , 116 : 6879 – 84 .
   PubMed Web of Science ®Google Scholar
• Reed , E. J. 2012 . Electron-Ion Coupling in Shocked Energetic Materials . J. Phys. Chem. C , 116 : 2205 – 11 .
   Web of Science ®Google Scholar
• Sharia , O. and Kuklja , M. M. 2011 . Modeling Thermal Decomposition Mechanisms in Gaseous and Crystalline Molecular Materials: Application to beta-HMX . J. Phys. Chem. B , 115 : 12677 – 86 .
   PubMed Web of Science ®Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Montgomery , J. A. , Vreven , T. , Kudin , K. N. , Burant , J. C. , Millam , J. M. , Iyengar , S. S. , Tomasi , J. , Barone , V. , Mennucci , B. , Cossi , M. , Scalmani , G. , Rega , N. , Petersson , G. A. , 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 , J. E. , Hratchian , H. P. , Cross , J. B. , Bakken , V. , Adamo , C. , Jaramillo , J. , Gomperts , R. , Stratmann , R. E. , Yazyev , O. , Austin , A. J. , Cammi , R. , Pomelli , C. , Ochterski , J. W. , Ayala , P. Y. , Morokuma , K. , Voth , G. A. , Salvador , P. , Dannenberg , J. J. , Zakrzewski , V. G. , Dapprich , S. , Daniels , A. D. , Strain , M. C. , Farkas , O. , Malick , D. K. , Rabuck , A. D. , Raghavachari , K. , Foresman , J. B. , Ortiz , J. V. , Cui , Q. , Baboul , A. G. , Clifford , S. , Cioslowski , J. , Stefanov , B. B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Martin , R. L. , Fox , D. J. , Keith , T. , Al Laham , M. A. , Peng , C. Y. , Nanayakkara , A. , Challacombe , M. , Gill , P. M. W. , Johnson , B. , Chen , W. , Wong , M. W. , Gonzalez , C. and Pople , J. A. 2003 . Gaussian 03 , Pittsburgh , PA : Gaussian, Inc. .
   Google Scholar
• Wei , T. , Zhu , W. H. , Zhang , J. and Xiao , H. M. 2010 . DFT Study on Energetic Tetrazolo-[1,5-b]- 1,2,4,5-tetrazine and 1,2,4-Triazolo-[4,3-b]-1,2,4,5-tetrazine Derivatives . J. Hazard. Mater. , 179 : 581 – 90 .
   PubMed Web of Science ®Google Scholar
• Fan , X. W. , Ju , X. H. and Xiao , H. M. 2008 . Density Functional Theory Study of Piperidine and Diazocine Compounds . J. Hazard. Mater. , 156 : 342 – 7 .
   PubMed Web of Science ®Google Scholar
• Wei , T. , Zhu , W. H. , Zhang , X. W. , Li , Y. F. and Xiao , H. M. 2009 . Molecular Design of 1,2,4,5-Tetrazine-based High-Energy Density Materials . J. Phys. Chem. A , 113 : 9404 – 12 .
   PubMed Web of Science ®Google Scholar
• Wang , G. X. , Gong , X. D. , Liu , Y. and Xiao , H. M. 2010 . A Theoretical Investigation on the Structures, Densities, Detonation Properties, and Pyrolysis Mechanism of the Nitro Derivatives of Phenols . Int. J. Quantum Chem. , 110 : 1691 – 701 .
   Web of Science ®Google Scholar
• Zhang , G. H. , Zhao , Y. F. , Hao , F. Y. , Zhang , P. X. and Song , X. D. 2009 . Theoretical Study on Structures and Stabilities of N4X (X = O, S, Se, Te) Series . Int. J. Quantum. Chem. , 109 : 226 – 35 .
   Web of Science ®Google Scholar
• Becke , A. D. 1992 . Density-functional Thermochemistry. II. The Effect of the Perdew-Wang Generalized-gradient Correlation Correction . J. Chem. Phys. , 97 : 9173 – 7 .
   Web of Science ®Google Scholar
• Hill , T. L. 1960 . Introduction to Statistic Thermodynamics , New York : Addison-Wesley .
   Google Scholar
• Kamlet , M. J. and Jacobs , S. J. 1968 . A Simple Method for Calculating Detonation Properties of C [single bond] H [single bond] N [single bond] O Explosives . J. Chem. Phys. , 48 : 23 – 35 .
   Web of Science ®Google Scholar
• Zhang , X. H. and Yun , Z. H. 1989 . Explosive Chemistry , Beijing : National Defence Industry Press .
   Google Scholar
• 2008 . Materials Studio 4.4 , San Diego , CA : Accelrys, Inc. .
   Google Scholar
• Sun , H . 1998 . COMPASS: An ab Initio Force-Field Optimized for Condensed-Phase Applications-Overview with Details on Alkane and Benzene Compounds . J. Phys. Chem. B , 102 : 7338 – 64 .
   Web of Science ®Google Scholar
• Xu , X. J. , Zhu , W. H. and Xiao , H. M. 2007 . “ DFT Studies on the Four Polymorphs of Crystalline CL-20 and the Influences of Hydrostatic Pressure on Epsilon-CL-20 Crystal ” . In J. Phys. Chem. B Vol. 111 , 2090 – 7 .
   Google Scholar
• Xu , X. J. , Zhu , W. H. and Xiao , H. M. 2008 . Molecular Packing Prediction and Periodic Calculations on Three Polynitroadamantanes as Potential High Energy Density Compounds . Chin. J. Chem. , 26 : 602 – 6 .
   Web of Science ®Google Scholar
• 1988 . Space Groups Rare for Organic Structures. I. Triclinic, Monoclinic and Orthorhombic Crystal Classes . Acta Crystallogr., Sect. A: Found. Crystallogr. , 44 : 715 – 24 .
   Web of Science ®Google Scholar
• Mighell , A. D. , Himes , V. L. and Rodgers , J. 1983 . Space-group Frequencies for Organic Compounds . Acta Crystallogr., Sect. A: Found. Crystallogr. , 39 : 737 – 40 .
   Web of Science ®Google Scholar
• Lide , D. R. 2002 . CRC Handbook of Chemistry and Physics , Boca Raton , FL : CRC Press LLC .
   Google Scholar
• Jursic , B. S. 1997 . A Density Functional Theory Estimation of the Heat of Formation for FOOCl . J. Chem. Phys. , 106 : 2555 – 6 .
   Web of Science ®Google Scholar
• Scott , A. P. and 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 – 13 .
   Web of Science ®Google Scholar
• Agrawal , J. P. and Hodgson , R. D. 2007 . Organic Chemistry of Explosives , New York : John Wiley & Sons .
   Google Scholar
• Pagoria , P. F. , Lee , J. S. , Mitchell , A. R. and Schmidt , R. D. 2002 . A Review of Energetic Materials Synthesis . Thermochim. Acta. , 384 : 187 – 204 .
   Web of Science ®Google Scholar
• Fukui , K. 1975 . Theory of Orientation and Stereoselection, Reactivity and Structure, Concepts in Organic Chemistry , Berlin : Springer .
   Google Scholar
• Scrocco , E. and Tomasi , J. 1973 . The Electrostatic Molecular Potential as a Tool for the Interpretation of Molecular Properties . Top. Curr. Chem. , 42 : 95 – 170 .
   Google Scholar