Crystal Engineering of Energetic Materials: Co‐crystals of Ethylenedinitramine (EDNA) with Modified Performance and Improved Chemical Stability

Aakeröy, Christer B.; Wijethunga, Tharanga K.; Desper, John

doi:10.1002/chem.201501721

Cited by 89 publications

(86 citation statements)

References 58 publications

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“…As one of the active research topics, cocrystallization of energetic coformers provides an opportunity to obtain new explosives from established components . Normally, promising cocrystal explosives consist of a high‐energy component and an insensitive one at a certain ratio, which are stabilized by noncovalent interactions such as hydrogen bonds, p–π stacking, π–π stacking as well as halogen bonds . The ease of rupture for trigger linkage of energetic molecules is regulated by vibrations of inter‐ and intra‐ molecular interactions and vibrational energy redistributions, thus it allows tuning the crucial properties of the explosives including density and sensitivity .…”

Section: Introductionmentioning

confidence: 99%

Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability

Liu

Duan²,

et al. 2019

Propellants Explo Pyrotec

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In this study, the energetic 2,4,6,8,10,12‐hexanitrohexaazaisowurtzitane/2,4‐dinitro‐2,4‐diazapentane (CL‐20/DNDAP) cocrystals were successfully fabricated via an efficient self‐assembly strategy. The formation processes of CL‐20/DNDAP cocrystal in solvents of H2O, H2O/methyl acetate, and 2‐propanol have been investigated by using the powder X‐ray diffraction (PXRD) qualitative/quantitative analysis and scanning electron microscopy (SEM). Both theoretical and experimental studies confirmed that the most satisfying results can be achieved by using 2‐propanol at 30 °C with crystallization time of 2 h, with a high yield up to 98.2 %. The addition of sodium dodecyl benzene sulfonate (SDBS) is effective in controlling its morphology with a narrow size distribution. Furthermore, the cocrystal exhibits better thermal stability and improved mechanical sensitivity compared with the one prepared by spray drying method. This work provides a simple and convenient approach for the preparation of energetic cocrystals, and the CL‐20/DNDAP cocrystal with high energy and low sensitivity is desirable for various applications.

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Section: Introductionmentioning

confidence: 99%

Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability

Liu

Duan²,

et al. 2019

Propellants Explo Pyrotec

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“…This approach has been widely used in pharmaceutical field to improve the solubility and/or stability of either component of the co-crystal. In the area of energetic materials, co-crystallization is emerging as a new technology for modifying or enhancing the properties of existing energetic substances [2].Therefore co-crystallisation would potentially provide a way to achieve the combination of high energy and low sensitivity on the molecular level [3].…”

Section: Introductionmentioning

confidence: 99%

Explosive performance of HMX/NTO co-crystal

Li¹,

Jiao

Gong³

et al. 2018

IOP Conf. Ser.: Mater. Sci. Eng.

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Abstract.A new co-crystal explosive of 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) and 3-nitro-1, 2, 4-triazol-5-one (NTO) in a molar ratio of 1:1 has been prepared by solvent/antisolvent method. The SEM photographs show that HMX/NTO co-crystals are distinctly different from HMX and NTO crystals. The co-crystals are prisms with well formed crystal surfaces. Thermal analysis results indicate the melting point of the co-crystal is 29.3℃higher than that of NTO. Moreover, the co-crystal exhibits a modified mechanical sensitivity. The characteristic height (H 50 ) of impact sensitivity increases 14.8cm, and the explosion percentage (P) of friction sensitivity decreases by 40% compared with HMX. The HMX/NTO co-crystals possess good thermal property and low sensitivity, which mean huge advantages in blasting engineering.

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“…N‐oxides have been attracting attention because of their potential applications in crystal materials and biological systems . For example, a large number of tertiary amine drugs produce N‐oxides as metabolites or intermediates in drug metabolism .…”

Section: Introductionmentioning

confidence: 99%

Tetrel bonds between PhSiF₃/PhTH₃(T = Si, Ge, Sn) and H₃ZO (Z = N, P, As): A pentacoordinate silicon (IV) complex

Cheng

et al. 2018

Int J of Quantum Chemistry

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The nature of the complexes PhTH 3 AH 3 ZO and PhSiF 3 AH 3 ZO (T 5 Si, Ge, and Sn; Z 5 N, P, and As) has been investigated at the MP2/aug'-cc-pVTZ(PP) level. These complexes are primarily stabilized by one TÁÁÁO tetrel bond. Interaction energies of these complexes vary from 11 to 220 kJ/mol, and TÁÁÁO separations from 1.89 to 3.09 Å. Charge transfer from the O lone pair into the CAT and TAH r* antibonding orbitals leads to the stabilization of these complexes. The TÁÁÁO tetrel bond between PhTH 3 /PhSiF 3 and H 3 NO exhibits a significant degree of covalence, characterized by the large interaction energy, negative energy density, and large charge transfer.Furthermore, a pentacoordinate silicon (IV) complex is formed in PhSiF 3 AH 3 NO with the SiÁÁÁO distance almost close to the length of SiAO bond. This indicates that the oxygen atom in N-oxides shows a strong affinity to the silicon atom in organosilicon compounds. K E Y W O R D S ab initio calculations, N-oxides, pentacoordinate silicon (IV) complex, phenyltrifluorosilane, tetrel bonds 1 | I N T R O D U C T I O NN-oxides have been attracting attention because of their potential applications in crystal materials [1][2][3] and biological systems. [4][5][6] For example, a large number of tertiary amine drugs produce N-oxides as metabolites or intermediates in drug metabolism. [4] The NAO bond in N-oxides is classified as the N!O donating bond with an important contribution from the O!N back-donation. The NAO bond in pyridine-N-oxide is stabilized and destabilized by an electron-withdrawing group (ANO 2 ) and an electron-donating substituent (ANH 2 ), respectively. [7] The character of NAO bond in N-oxides renders the oxygen atom as a potential electron donor to form noncovalent interactions including hydrogen bonds, [7][8][9][10][11][12] halogen bonds, [7,[13][14][15][16][17][18] and chalcogen bonds. [19] Prezhdo and coworkers found that pyridine-N-oxides and proton donors could form hydrogen-bonded complex, and its stability is primarily dependent on steric conditions of pyridine-N-oxides. [9] These studies showed that the oxygen atom of N-oxides is a very good electron donor. Generally, nitrogen atom is a better electron donor than oxygen atom, but the reverse is true when the nitrogen atom of pyridine derivatives and the oxygen atom of the corresponding N-oxides are compared. [13] Like N-oxides, phosphine oxides are also potential electron donors in hydrogen bonds [10,[20][21][22] and halogen bonds. [14,[22][23][24][25] Alkorta et al., found that phosphine oxides can form eclipsed and staggered hydrogen-bonded complexes with similar stabilities. [10] Generally, the hydrogen/halogen bond involving phosphine oxides is weaker than that involving amine oxides. Phosphine oxides have a shorter bond length of PAO than that of NAO in amine oxides due to the stronger electrostatic interaction between P and O, [26] This partly results in a lower dipole moment of a phosphine oxide, indicating that it is a weaker electron donor. On the formation of a halogen bond, the ox...

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Crystal Engineering of Energetic Materials: Co‐crystals of Ethylenedinitramine (EDNA) with Modified Performance and Improved Chemical Stability

Cited by 89 publications

References 58 publications

Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability

Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability

Explosive performance of HMX/NTO co-crystal

Tetrel bonds between PhSiF₃/PhTH₃(T = Si, Ge, Sn) and H₃ZO (Z = N, P, As): A pentacoordinate silicon (IV) complex

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Crystal Engineering of Energetic Materials: Co‐crystals of Ethylenedinitramine (EDNA) with Modified Performance and Improved Chemical Stability

Cited by 89 publications

References 58 publications

Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability

Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability

Explosive performance of HMX/NTO co-crystal

Tetrel bonds between PhSiF3/PhTH3(T = Si, Ge, Sn) and H3ZO (Z = N, P, As): A pentacoordinate silicon (IV) complex

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Tetrel bonds between PhSiF₃/PhTH₃(T = Si, Ge, Sn) and H₃ZO (Z = N, P, As): A pentacoordinate silicon (IV) complex