Computational Evaluation of Polycyclic Bis-Oxadiazolo-Pyrazine Backbone in Designing Potential Energetic Materials

References

• H. Gao and J. M. Shreeve, “Azole-Based Energetic Salts,” Chemical Reviews 111, no. 11 (2011): 7377–436.
   PubMed Web of Science ®Google Scholar
• H. Gao, Q. Zhang, and J. M. Shreeve, “Fused Heterocycle-Based Energetic Materials (2012–2019),” Journal of Materials Chemistry A 8, no. 8 (2020): 4193–216.
   Web of Science ®Google Scholar
• S. Banik, A. K. Yadav, P. Kumar, V. D. Ghule, and S. Dharavath, “Unfolding the Chemistry of FOX-7: Unique Energetic Material and Precursor with Numerous Possibilities,” Chemical Engineering Journal 431 (2022): 133378.
   Web of Science ®Google Scholar
• S. Manzoor, Q. Tariq, X. Yin, and J. G. Zhang, “Nitro-Tetrazole Based High Performing Explosives: Recent Overview of Synthesis and Energetic Properties,” Defence Technology 17, no. 6 (2021): 1995–2010.
   Web of Science ®Google Scholar
• T. M. Klapötke, Chemistry of High-Energy Materials, 4th Edition (Berlin/Boston: Walter de Gruyter Gmbh, 2017).
   Google Scholar
• J. T. Wu, J. Xu, W. Li, and H. B. Li, “Coplanar Fused Heterocycle‐Based Energetic Materials,” Propellants, Explosives, Pyrotechnics 45, no. 4 (2020): 536–45.
   Web of Science ®Google Scholar
• S. Chen, Y. Jin, H. Xia, K. Wang, Y. Liu, and Q. Zhang, “Synthesis of Fused Tetrazolo[1,5-b]Pyridazine-Based Energetic Compounds,” Energetic Materials Frontiers 1, no. 1 (2020): 16–25.
   Google Scholar
• C. Bian, X. Dong, X. Zhang, Z. Zhou, M. Zhang, and C. Li, “The Unique Synthesis and Energetic Properties of a Novel Fused Heterocycle: 7-Nitro-4-Oxo-4,8-Dihydro-[1,2,4]Triazolo[5,1-d][1,2,3,5]Tetrazine 2-Oxide and Its Energetic Salts,” Journal of Materials Chemistry A 3, no. 7 (2015): 3594–601.
   Web of Science ®Google Scholar
• E. B. Rakhimova, V. Y. Kirsanov, E. S. Mescheryakova, L. U. Dzhemileva, V. A. D’yakonov, A. G. Ibragimov, and U. M. Dzhemilev, “Synthesis and Cytotoxic Activity of New Annulated Furazan Derivatives,” Mendeleev Communications 31, no. 3 (2021): 362–4.
   Web of Science ®Google Scholar
• A. B. Sheremetev, and I. L. Yudin, “Synthesis of Unsubstituted 4H,8H-Bisfurazano[3,4-b:3′,4′-e]Pyrazine,” Mendeleev Communications 6, no. 6 (1996): 247–8.
   Google Scholar
• B. H. Duan, N. Liu, B. Z. Wang, and X. M. Lu, “Synthesis, Crystal Structure and Properties of Aminourea Salt of 4,8-Dihydrodifurazano[3,4-b,e] Pyrazine,” Journal of Physics: Conference Series 1507, no. 2 (2020): 022029.
   Google Scholar
• W. Li, K. Wang, X. Qi, Y. Jin, and Q. Zhang, “Construction of a Thermally Stable and Highly Energetic Metal-Organic Framework as Lead-Free Primary Explosives,” Crystal Growth & Design 18, no. 3 (2018): 1896–902.
   Web of Science ®Google Scholar
• E. B. Rakhimova, V. Y. Kirsanov, E. S. Mescheryakova, L. M. Khalilov, A. G. Ibragimov, L. U. Dzhemileva, V. A. D'yakonov, and U. M. Dzhemilev, “First Example of Catalytic Synthesis of Difurazanohexahydrohexaazapyrenes and in Vitro Study of Their Antitumor Activity,” ACS Medicinal Chemistry Letters 10, no. 3 (2019): 378–82.
   PubMed Web of Science ®Google Scholar
• A. B. Sheremetev, V. L. Korolev, A. A. Potemkin, N. S. Aleksandrova, N. V. Palysaeva, T. H. Hoang, V. P. Sinditskii, and K. Y. Suponitsky, “Oxygen-Rich 1,2,4-Triazolo[3,4-d]-1,2,4-Triazolo[3,4-f]Furazano[3,4-b]Pyrazines as Energetic Materials,” Asian Journal of Organic Chemistry 5, no. 11 (2016): 1388–97.
   Web of Science ®Google Scholar
• N. Liu, Y. J. Shu, H. Li, L. J. Zhai, Y. Li, and B. Z. Wang, “Synthesis, Characterization and Properties of Heat-Resistant Explosive Materials: Polynitroaromatic Substituted Difurazano[3,4-b:3′,4′-e]Pyrazines,” RSC Advances 5, no. 54 (2015): 43780–5.
   Web of Science ®Google Scholar
• C. J. Snyder, L. A. Wells, D. E. Chavez, G. H. Imler, and D. A. Parrish, “Polycyclic N-Oxides: High Performing, Low Sensitivity Energetic Materials,” Chemical Communications 55, no. 17 (2019): 2461–4.
   PubMed Web of Science ®Google Scholar
• Q. Sun, X. Li, Q. Lin, and M. Lu, “Tetracyclic Pyrazine-Fused Furazans as Insensitive Energetic Materials: Syntheses, Structures, and Properties,” Organic & Biomolecular Chemistry 16, no. 43 (2018): 8034–7.
   PubMed Web of Science ®Google Scholar
• B. B. Averkiev, A. A. Korlyukov, M. Y. Antipin, A. B. Sheremetev, and T. V. Timofeeva, “Experimental X-Ray Diffraction Study of Stacking Interaction in Crystals of Two Furazan[3,4-b]Pyrazines,” Crystal Growth & Design 14, no. 11 (2014): 5418–27.
   Web of Science ®Google Scholar
• W. Li, J. Tian, X. Qi, K. Wang, Y. Jin, B. Wang, and Q. Zhang, “Synthesis of 4,8-Dinitraminodifurazano[3, 4-b,e] Pyrazine Derived Nitrogen-Rich Salts as Potential Energetic Materials,” ChemistrySelect 3, no. 2 (2018): 849–54.
   Web of Science ®Google Scholar
• Q. Zhang, C. Zhao, X. Zhang, C. He, and S. Pang, “Oxidation of O-Dioxime by (Diacetoxyiodo)Benzene: Green and Mild Access to Furoxans,” New Journal of Chemistry 46, no. 4 (2022): 1489–93.
   Web of Science ®Google Scholar
• R. L. Willer and D. W. Moore, “Synthesis and Chemistry of Some Furazano- and Furoxano[3,4-b]Piperazines,” The Journal of Organic Chemistry 50, no. 25 (1985): 5123–7.
   Web of Science ®Google Scholar
• B. Duan, N. Liu, B. Wang, X. Lu, and H. Mo, “Comparative Theoretical Studies on a Series of Novel Energetic Salts Composed of 4,8-Dihydrodifurazano[3,4-b,e]Pyrazine-Based Anions and Ammonium-Based Cations,” Molecules 24, no. 18 (2019): 3213.
   PubMed Web of Science ®Google Scholar
• D. B. Lempert, A. I. Kazakov, A. B. Sheremetev, A. G. Gladyshkin, A. V. Nabatova, and L. S. Yanovskii, “Experimental Determination of the Standard Enthalpy of Formation of 4H,8H-Bis(Furazano)[3,4-b:3′,4′-e]Pyrazine and Evaluation of Its Performance as a Dispersant of Solid Fuels,” Russian Chemical Bulletin 68, no. 10 (2019): 1856–9.
   Web of Science ®Google Scholar
• Y. N. Li, N. Liu, P. F. Su, Y. L. Wang, Z. X. Ge, H. Li, and B. Z. Wang, “Synthesis and Structural Characterization of N-Amino Compounds,” Asian Journal of Chemistry 26, no. 21 (2014): 7151–6.
   Google Scholar
• I. B. Starchenkov, V. G. Andrianov, and A. F. Mishnev, “Chemistry of Furazano[3,4-b]Pyrazine. 1. Synthesis and Thermodynamic Appraisal of 4,8-Dihydrodifurazano[3,4-b,e]Pyrazine and Its Derivatives,” Chemistry of Heterocyclic Compounds 33, no. 2 (1997): 216–28.
   Google Scholar
• B. B. Averkiev, M. Y. Antipin, I. L. Yudin, and A. B. Sheremetev, “X-Ray Structural Study of Three Derivatives of Dinitropyrazine,” Journal of Molecular Structure 606, no. 1–3 (2002): 139–46.
   Web of Science ®Google Scholar
• C. J. Snyder, G. H. Imler, D. E. Chavez, and D. A. Parrish, “Synergetic Explosive Performance through Cocrystallization,” Crystal Growth & Design 21, no. 3 (2021): 1401–5.
   Web of Science ®Google Scholar
• 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, et al, Gaussian 09, Revision E.01 (Wallingford CT: Gaussian, Inc.. 2013).
   Google Scholar
• V. D. Ghule, “Computational Studies on the Triazole-Based High Energy Materials,” Computational and Theoretical Chemistry 992 (2012): 92–6.
   Web of Science ®Google Scholar
• A. Devi, V. D. Ghule, and A. Nirwan, “Replacement of an Azide Group with Carbonyl‐Azide in Nitrogen‐Rich Energetic Materials: Searching for Possible Alternatives with a Computational Approach,” ChemistrySelect 3, no. 30 (2018): 8651–5.
   Web of Science ®Google Scholar
• A. Nirwan, A. Devi, and V. D. Ghule, “Theoretical Determination of the Effects of Various Linkages between Trinitrobenzenes on Energetic Properties and Sensitivity,” Journal of Molecular Modeling 25, no. 10 (2019): 315.
   PubMed Web of Science ®Google Scholar
• A. Maan, R. S. Mathpati, and V. D. Ghule, “Substituted Triazolo-Triazine Derivatives as Energetic Materials: A Computational Investigation and Assessment,” Journal of Molecular Modeling 26, no. 7 (2020): 184.
   PubMed Web of Science ®Google Scholar
• P. Politzer, J. S. Murray, M. E. Grice, M. Desalvo, and E. Miller, “Calculation of Heats of Sublimation and Solid Phase Heats of Formation,” Molecular Physics 91, no. 5 (1997): 923–8.
   Web of Science ®Google Scholar
• E. F. C. Byrd, and B. M. Rice, “Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations,” The Journal of Physical Chemistry. A 110, no. 3 (2006): 1005–13.
   PubMed Web of Science ®Google Scholar
• M. A. Suntsova, and O. V. Dorofeeva, “Prediction of Enthalpies of Sublimation of High-Nitrogen Energetic Compounds: Modified Politzer Model,” Journal of Molecular Graphics & Modelling 72 (2017): 220–8.
   PubMed Web of Science ®Google Scholar
• L. Huang, and L. Massa, “Applications of Energetic Materials by a Theoretical Method (Discover Energetic Materials by a Theoretical Method),” International Journal of Energetic Materials and Chemical Propulsion 12, no. 3 (2013): 197–262.
   Google Scholar
• Y. Pan, W. Zhu, and H. Xiao, “Theoretical Studies on the Structures, Heats of Formation, Energetic Properties and Pyrolysis Mechanisms of Nitrogen-Rich Difurazano[3,4-b:3′,4′-e]Piperazine Derivatives and Their Analogues,” Structural Chemistry 24, no. 4 (2013): 1071–87.
   Web of Science ®Google Scholar
• V. P. Sinditskii, A. D. Smirnova, V. V. Serushkin, N. S. Aleksandrova, and A. B. Sheremetev, “Furazan‐Fused Azacyclic Nitramines: Influence of Structural Features on the Combustion and the Thermolysis,” ChemistrySelect 5, no. 44 (2020): 13868–77.
   Web of Science ®Google Scholar
• L. Qiu, H.-M. Xiao, W.-H. Zhu, X.-H. Xiao, and X.-D. Gong, “Theoretical Study on the High Energy Density Compound Hexanitrohexaazatricyclotetradecanedifuroxan,” Chinese Journal of Chemistry 24, no. 11 (2006): 1538–46.
   Web of Science ®Google Scholar
• H. Muthurajan, R. Sivabalan, N. P. Saravanan, and M. B. Talawar, “Computer Code to Predict the Heat of Explosion of High Energy Materials,” Journal of Hazardous Materials 161, no. 2–3 (2009): 714–7.
   PubMed Web of Science ®Google Scholar
• H. Muthurajan, R. Sivabalan, M. B. Talawar, and S. N. Asthana, “Computer Simulation for Prediction of Performance and Thermodynamic Parameters of High Energy Materials,” Journal of Hazardous Materials 112, no. 1-2 (2004): 17–33.
   PubMed Web of Science ®Google Scholar
• P. Politzer, J. Martinez, J. S. Murray, M. C. Concha, and A. Toro-Labbé, “An Electrostatic Interaction Correction for Improved Crystal Density Prediction,” Molecular Physics 107, no. 19 (2009): 2095–101.
   Web of Science ®Google Scholar
• M. J. Kamlet and S. J. Jacobs, “Chemistry of Detonations. I. A Simple Method for Calculating Detonation Properties of C–H–N–O Explosives,” The Journal of Chemical Physics 48, no. 1 (1968): 23–35.
   Web of Science ®Google Scholar
• M. J. Kamlet and J. E. Ablard, “Chemistry of Detonations. II. Buffered Equilibria,” The Journal of Chemical Physics 48, no. 1 (1968): 36–42.
   Web of Science ®Google Scholar
• D. M. Badgujar, M. B. Talawar, S. N. Asthana, and P. P. Mahulikar, “Advances in Science and Technology of Modern Energetic Materials: An Overview,” Journal of Hazardous Materials 151, no. 2–3 (2008): 289–305.
   PubMed Web of Science ®Google Scholar
• P. Politzer, and J. S. Murray, “High Performance, Low Sensitivity: Conflicting or Compatible?,” Propellants Explosives, Pyrotechnics 41, no. 3 (2016): 414–25.
   Web of Science ®Google Scholar
• H. H. Licht, “Performance and Sensitivity of Explosives,” Propellants, Explosives, Pyrotechnics 25, no. 3 (2000): 126–32.
   Web of Science ®Google Scholar
• Z. X. Chen and H. M. Xiao, “Quantum Chemistry Derived Criteria for Impact Sensitivity,” Propellants Explosives, Pyrotechnics 39, no. 4 (2014): 487–95.
   Web of Science ®Google Scholar
• D. Mathieu, “Sensitivity of Energetic Materials: Theoretical Relationships to Detonation Performance and Molecular Structure,” Industrial & Engineering Chemistry Research 56, no. 29 (2017): 8191–201.
   Web of Science ®Google Scholar
• X. Xiong, X. He, Y. Xiong, X. Xue, H. Yang, and C. Zhang, “Correlation between the Self-Sustaining Ignition Ability and the Impact Sensitivity of Energetic Materials,” Energetic Materials Frontiers 1, no. 1 (2020): 40–9.
   Google Scholar
• P. Politzer and J. S. Murray, “Impact Sensitivity and the Maximum Heat of Detonation,” Journal of Molecular Modeling 21, no. 10 (2015): 262.
   PubMed Web of Science ®Google Scholar
• J. Joy, D. Danovich, and S. Shaik, “Nature of the Trigger Linkage in Explosive Materials is a Charge-Shift Bond,” The Journal of Organic Chemistry 86, no. 21 (2021): 15588–96.
   PubMed Web of Science ®Google Scholar
• T. L. Jensen, J. F. Moxnes, E. Unneberg, and D. Christensen, “Models for Predicting Impact Sensitivity of Energetic Materials Based on the Trigger Linkage Hypothesis and Arrhenius Kinetics,” Journal of Molecular Modeling 26, no. 4 (2020): 65.
   PubMed Web of Science ®Google Scholar
• G. Li, and C. Zhang, “Review of the Molecular and Crystal Correlations on Sensitivities of Energetic Materials,” Journal of Hazardous Materials 398 (2020): 122910.
   PubMed Web of Science ®Google Scholar
• S. V. Bondarchuk, “Quantification of Impact Sensitivity Based on Solid-State Derived Criteria,” The Journal of Physical Chemistry A 122, no. 24 (2018): 5455–63.
   PubMed Web of Science ®Google Scholar
• S. Zeman and M. Jungová, “Sensitivity and Performance of Energetic Materials,” Propellants, Explosives, Pyrotechnics 41, no. 3 (2016): 426–51.
   Web of Science ®Google Scholar
• D. Mathieu and T. Alaime, “Impact Sensitivities of Energetic Materials: Exploring the Limitations of a Model Based Only on Structural Formulas,” Journal of Molecular Graphics & Modelling 62 (2015): 81–6.
   PubMed Web of Science ®Google Scholar
• D. Mathieu, and T. Alaime, “Predicting Impact Sensitivities of Nitro Compounds on the Basis of a Semi-Empirical Rate Constant,” The Journal of Physical Chemistry A 118, no. 41 (2014): 9720–6.
   PubMed Web of Science ®Google Scholar