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Theoretical study on the structure, electronic properties, intermolecular interactions, and detonation performance of DAF:ADNP co-crystal

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Abstract

Context

Explosives have a wide range of applications in many fields due to their high energy and high density. Recently, a new synthesized co-crystal explosive DAF:ADNP presents high detonation performance and low sensitivity. This work is aimed to understand how the structure and intermolecular interactions affect the performance of the DAF:ADNP co-crystal. The results indicate that the formed π–π interactions and stronger hydrogen bonds in the co-crystal enhance its stability and its impact sensitivity is reduced. The strong intralayer H···N and H···O interactions and interlayer π–π stacking are the main driving force for the formation of the co-crystal. Compared with the pure crystals, the detonation performance of the co-crystal slightly decreases, while its sensitivity reduces.

Methods

All calculations were used the DFT-PBE-D method with Vanderbilt-type ultrasoft pseudopotentials and plane wave (340.0 eV) in the CASTEP package. Radial distribution function were calculated by NVT-MD simulations for 100 ps with a time step of 1 fs at 298 K. Hirshfeld surfaces were generated by CrystalExplorer 3.0 and reduced density gradient analyses were performed by Multiwfn 3.0.

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Data availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

References

  1. Thottempudi V, Gao HX, Shreeve JM (2011) Trinitromethylsubstituted 5-nitro- or 3-azo-1,2,4-triazoles: synthesis, characterization, and energetic properties. J Am Chem Soc 133:6464–6471

    Article  CAS  PubMed  Google Scholar 

  2. Wu Q, Tan LH, Hang ZS, Wang JY, Zhang ZW, Zhu WH (2015) A new design strategy on cage insensitive high explosives: symmetrically replacing carbon atoms by nitrogen atoms followed by the introduction of N-oxides. RSC Adv 5:93607–93614

    Article  CAS  Google Scholar 

  3. Wu Q, Zhu WH, Xiao HM (2014) A new design strategy for high-energy low-sensitivity explosives: combining oxygen balance equal to zero, a combination of nitro and amino groups, and noxide in one molecule of 1-amino-5-nitrotetrazole-3N-oxide. J Mater Chem A 2:13006–13015

    Article  CAS  Google Scholar 

  4. Sikder AK, Sikder N (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

    Article  CAS  PubMed  Google Scholar 

  5. Rice BM, Hare JJ, Byrd EFC (2007) Accurate predictions of crystal densities using quantum mechanical molecular volumes. J Phys Chem A 111:10874–10879

    Article  CAS  PubMed  Google Scholar 

  6. Hang GY, Yu WL, Wang T, Wang JT, Li Z (2017) Theoretical insights into effects of molar ratios on stabilities, mechanical properties and detonation performance of CL-20/RDX co-crystal explosives by molecular dynamics simulation. J Mol Struct 1141:577–583

    Article  CAS  Google Scholar 

  7. Guo DZ, An Q, Zybin SV, Goddard WA, Huang FL, Tang B (2015) The co-crystal of TNT/CL-20 leads to decreased sensitivity toward thermal decomposition from first principles based reactive molecular dynamics. J Mater Chem A 3:5409–5419

    Article  CAS  Google Scholar 

  8. Hang GY, Yu WL, Wang T, Wang JT, Li Z (2017) Comparative studies on structures, mechanical properties, sensitivity, stabilities and detonation performance of CL-20/TNT co-crystal and composite explosives by molecular dynamics simulation. J Mol Model 23:281

    Article  PubMed  Google Scholar 

  9. Sun T, Xiao JJ, Liu Q, Zhao F, Xiao HM (2014) Comparative study on structure, energetic and mechanical properties of a ε-CL-20/HMX co-crystal and its composite with molecular dynamics simulation. J Mater Chem A 2:13898–13904

    Article  CAS  Google Scholar 

  10. Bolton O, Simke LR, Pagoria PF, Matzger AJ (2012) High power explosive with good sensitivity: a 2:1 co-crystal of CL-20:HMX. Cryst Growth Des 12:4311–4314

    Article  CAS  Google Scholar 

  11. Xue XG, Ma Y, Zeng Q, Zhang CY (2017) Initial decay mechanism of the heated CL-20/HMX co-crystal: a case of the co-crystal mediating the thermal stability of the two pure components. J Phys Chem C 121:4899–4908

    Article  CAS  Google Scholar 

  12. Chen PY, Zhang L, Zhu SG, Cheng GB, Li NR (2017) Investigation of TNB/NNAP co-crystal synthesis, molecular interaction and formation process. J Mol Struct 1128:629–635

    Article  CAS  Google Scholar 

  13. Sen N (2018) A 1:1 energetic co-crystal formed between trinitrotoluene and 2,3-diaminotoluene. Maced J Chem Chem En 37:61–69

    Article  CAS  Google Scholar 

  14. Shen JP, Duan XH, Luo QP, Zhou Y, Bao QL, Ma YJ, Pei CH (2011) Preparation and characterization of a novel co-crystal explosive. Cryst Growth Des 11:1759–1765

    Article  CAS  Google Scholar 

  15. Bolton O, Matzger AJ (2011) Improved stability and smart-material functionality realized in an energetic cocrystal. Angew Chem 123:9122–9125

    Article  Google Scholar 

  16. Zhu SM, Ji JC, Zhu WH (2020) Intermolecular interactions, vibrational spectra, and detonation performance of CL-20/TNT co-crystal. J Chin Chem Soc 42:1–11

    Google Scholar 

  17. Ji JC, Zhu WH (2020) Theoretical studies on the role of each component in benzotrifuroxan:2,4,6-trinitrotoluene co-crystal. Chem Phys Lett 753:137608

    Article  CAS  Google Scholar 

  18. Zelenin AK, Trudell ML (1997) A two-step synthesis of diaminofurazan and synthesis of N-monoarylmethyl and N, N’-diarylmethyl derivatives. J Heterocyclic Chem 34:1057–1060

    Article  CAS  Google Scholar 

  19. Stoner CE, Brill TB (1991) Thermal decomposition of energetic materials 46. The formation of melamine-like cyclic azines as a mechanism for ballistic modification of composite propellants by DCD, DAG, and DAF. Combust Flame 83:302–308

    Article  CAS  Google Scholar 

  20. Bennion JC, Siddiqi ZR, Matzger AJ (2017) A melt castable energetic cocrystal. Chem Commun 53:6065–6068

    Article  CAS  Google Scholar 

  21. Schmidt RD, Lee GS, Pagoria PF, Mitchell AR, Gilardi R (2001) Synthesis of 4-amino-3,5-dinitro-1H-pyrazole using vicarious nucleophilic substitution of hydrogen. J Heterocyclic Chem 38:1227–1230

    Article  CAS  Google Scholar 

  22. Zhao GZ, Yang DF (2018) Periodic DFT study of structural transformations of cocrystal NTO/TZTN under high pressure. RSC Adv 8:32241–32251

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Payne MC, Teter MP, Allan DC, Arias TA, Joannopoulos JD (1992) Iterative minimization techniques for ab initio total-energy calculations: molecular dynamics and conjugate gradients. Rev Mod Phys 64:1045–1097

    Article  CAS  Google Scholar 

  24. Kresse G, Furthmüller J (1996) Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set. Phys Rev B 54:11169–11186

    Article  CAS  Google Scholar 

  25. Fischer TH, Almlöf J (1992) General methods for geometry and wave function optimization. J Phys Chem 96:9768–9774

    Article  CAS  Google Scholar 

  26. Perdew JP, Burke K, Ernzerhof M (1996) Generalized gradient approximation made simple. Phys Rev Lett 77:3865–3868

    Article  CAS  PubMed  Google Scholar 

  27. Grimme S (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem 27:1787–1799

    Article  CAS  PubMed  Google Scholar 

  28. Zheng ZY, Zhao JJ, Sun YY, Zhang SB (2012) Structures and lattice energies of molecular crystals using density functional theory: assessment of a local atomic potential approach. Chem Phys Lett 550:94–98

    Article  CAS  Google Scholar 

  29. Mayo SL, Olafson BD, Goddard WA (1990) Dreiding: a generic force field for molecular simulations. J Phys Chem 94:8897–8909

    Article  CAS  Google Scholar 

  30. Karasawa N, Goddard WA (1992) Force fields, structures, and properties of poly(vinylidene fluoride) crystals. Macromolecules 25:7268–7281

    Article  CAS  Google Scholar 

  31. Sangster MJL, Dixon M (1976) Interionic potentials in alkali halides and their use in simulations of the molten salts. Adv Phys 25:247–342

    Article  CAS  Google Scholar 

  32. Wolff SK, Grimwood DJ, Mckinnon JJ, Turner MJ, Jayatilaka D, Spackman MA (2012) Crystal explorer 3.0. University of Western Australia

  33. Lu T, Chen FW (2012) Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem 33:580–592

    Article  PubMed  Google Scholar 

  34. Zhao X, Huang SL, Liu Y, Li JS, Zhu WH (2019) Effects of noncovalent interactions on the impact sensitivity of HNS-based cocrystals: a DFT study. Cryst Growth Des 19:756–767

    Article  CAS  Google Scholar 

  35. Tian BB, Xiong Y, Chen LZ, Zhang CY (2018) Relationship between the crystal packing and impact sensitivity of energetic materials. CrystEngComm 20:837–848

    Article  CAS  Google Scholar 

  36. Ma Y, Zhang AB, Zhang CH, Jiang DJ, Zhu YQ, Zhang CY (2014) Crystal packing of low-sensitivity and high-energy explosives. Cryst Growth Des 14:4703–4713

    Article  CAS  Google Scholar 

  37. Zhu W, Xiao H (2010) First-principles band gap criterion for impact sensitivity of energetic crystals: a review. Struct Chem 21:657–665

    Article  CAS  Google Scholar 

  38. Rice BM, Hare JJ (2002) A quantum mechanical investigation of the relation between impact sensitivity and the charge distribution in energetic molecules. J Phys Chem A 106:1770–1783

    Article  CAS  Google Scholar 

  39. Waseda Y (1980) The structure of non-crystalline materials. McGraw-Hill, New York

    Google Scholar 

  40. Xiong SL, Chen SS, Jin SL, Zhang CY (2016) Molecular dynamics simulations on dihydroxylammonium 5,5’-bistetrazole-1,1’-diolate/hexanitrohexaazaisowurtzitane cocrystal. RSC Adv 6:4221–4226

    Article  CAS  Google Scholar 

  41. Keshavarz MH (2007) Reliable estimation of performance of explosives without considering their heat contents. J Hazard Mater 147:826–831

    Article  CAS  PubMed  Google Scholar 

  42. Mader CL (1988) Numerical modeling of explosives and propellants. CRC Press

    Google Scholar 

  43. Keshavarz MH, Pouretedal HR (2006) Predicting adiabatic exponent as one of the important factors in evaluating detonation performance. Indian J Eng Mater Sci 13:259–263

    CAS  Google Scholar 

  44. Li JS (2010) Relationships for the impact sensitivities of energetic C-nitro compounds based on bond dissociation energy. J Phys Chem B 114:2198–2202

    Article  CAS  PubMed  Google Scholar 

  45. Liu H, Li QK, He YH (2013) Pyrolysis of CL-20-TNT co-crystal from ReaxFF/lg reactive molecular dynamics simulations. Acta Phys Sin 20:208202

    Article  Google Scholar 

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Funding

This research was supported by the National Natural Science Foundation of China (Grant No. 21773119).

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Authors and Affiliations

  1. Institute for Computation in Molecular and Materials Science, School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, China

    Li Tang & Weihua Zhu

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  1. Li Tang
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  2. Weihua Zhu
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Contributions

Conceptualization, design, material preparation, data collection, analysis, and writing—original draft preparation were performed by Li Tang. Supervision, conceptualization, writing—reviewing and editing, and funding acquisition were performed by Weihua Zhu.

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Correspondence to Weihua Zhu.

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Tang, L., Zhu, W. Theoretical study on the structure, electronic properties, intermolecular interactions, and detonation performance of DAF:ADNP co-crystal. J Mol Model 29, 191 (2023). https://doi.org/10.1007/s00894-023-05601-9

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