Oxaazatetracyclo[5.5.0.03, 10.05, 8]Dodecanes – a Promising Foundation for the Design of Thermally Stable, High-Density Energetic Compounds

Paromov, Artyom E.; Sysolyatin, S. V.

doi:10.1007/s10593-017-2105-x

Cited by 23 publications

(10 citation statements)

References 32 publications

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“…[38][39][40][41] Many research groups [42][43][44][45] over the past decades reported energetic materials rich in nitro groups. Selected examples of some familiar oxygen-rich and nitrogen rich explosives such as 1,3,5-trinitrotriazacyclohexane (RDX), [46] 1,3,5,7-tetranitrotetraazacyclooctane (HMX), [47] hexanitrobenzene (HNB), [48] trinitrotoluene (TNT), [49] 4,10-dinitro-4,10-diaza-2,6,8,12-tetraoxaisowurtzitane (TEX), [18,50] trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin (TNAD), [51] penta-erythritol tetranitrate (PETN), [52] hexanitrostilbene (HNS), [53] tetraazidomethane (TAM), [54] 2,2,4,4,6,6-hexanitroadamantane (HNA), [55] 4,4'-Azobis [1,2,4-triazole] (ABTr), [56] along with promising candidates for insensitive munitions (IM) such as 1,1-diamino-2,2-dinitroethylene (FOX-7), [57] 5-nitro-1,2,4triazole-3-one (NTO), [58] and triaminotrinitro benzene (TATB), [59] have been reported in literature.…”

Section: Introductionmentioning

confidence: 99%

Pentacycloundecane (PCUD)‐Based Cage Frameworks as Potential Energetic Materials: Syntheses and Characterization

et al. 2020

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A new variety of cage frameworks containing pentacycloundecane (PCUD) were synthesized. These compounds contain azide and triazole units. Four new cage frameworks were designed and constructed starting from easily accessible starting materials such as 2,3-dimethylhydroquinone, 1,4-dimethoxybenzene, and dicyclopentadiene using [2 + 2] photocycloaddition as the key step. The structures of these symmetrical cage bis-azide and cage bistriazole compounds have been confirmed by single-crystal X-ray diffraction studies. DFT analysis at different levels of theory were used to optimize the geometries and compute the heats of formation of the title compounds. Their propulsive and explosive properties were also calculated using suitable computational methods. The thermodynamic stability of the title compounds was theoretically analysed based on their bond dissociation energies. The thermal stability was evaluated by TGA-coupled FTIR analysis.

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Section: Introductionmentioning

confidence: 99%

Pentacycloundecane (PCUD)‐Based Cage Frameworks as Potential Energetic Materials: Syntheses and Characterization

et al. 2020

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“…Yet, the preparation of the latter EMs is challenging and frequently required many synthetic steps, resulting in low overall yields and high prices of the target materials, limiting their broader use and applications. Several well-known examples of the cage-type EMs include 2,4,6,8,10,12-hexanitrohexaazaisowurtizitane (CL-20), 4,10-dinitro-2,6,8,12-tetra-oxa-4,10-diazatetracyclo[5.5.0.0 5,9 .0 3,11 ]-dodecane (TEX), and octanitrocubane (ONC) . Therefore, designing EMs with a potentially high level of performance that could be prepared by straightforward synthetic approaches is very desirable but presents a formidable challenge.…”

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confidence: 99%

Design of Zero Oxygen Balance Energetic Materials on the Basis of Diels–Alder Chemistry

et al. 2018

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Herein, a novel zero oxygen balance polycyclic energetic compound trans-3,3,4,4,7,7,8,8-octanitro-9,10dioxatricyclo[4.2.1.1 2,5 ]-decane (trans-BIT) was designed and expected to exhibit high crystal density (ρ = 2.06 g/cm 3 ), outstanding detonation performance (D = 9.473 km/s, P = 42.2 GPa), and promising thermostability and sensitivity. We proposed that the synthesis of this compound could be achieved via a facile Diels−Alder reaction, using tetranitroethylene and oxadiazole as starting materials. We also predicted that the crystal structure of trans-BIT would have P2 1 /C space group symmetry.

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“…While selecting amides, we took into account the basicity of the reagents and the ease of N-nitration of the condensation products, except for mesyl amide that is highly resistant to acidic medium and capable of generating polyheterocyclic cage compounds. − The basicity of amides and the tendency of their condensation products toward N-nitration depends on the value of the partially negative charge on the amide nitrogen atom. This charge is due to the inductive effect of the substituent and increases in the row: CH 3 SO 2 NH 2 < HCONH 2 < CH 3 CONH 2 < (CH 3 ) 2 CHCONH 2 < CH 3 CH 2 CONH 2 < (CH 3 ) 3 CCONH 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Diaminoacetic Acid Derivatives as a Promising Scaffold for the Synthesis of Polyheterocyclic Cage Compounds

Paromov

Sysolyatin

2021

ACS Omega

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Here, we explored in detail an acid-catalyzed condensation of glyoxylic acid or its ethyl ester with several carboxamides of different basicity, or with mesyl amide, to furnish diaminoacetic acid derivatives. The most suitable synthesis conditions and the reaction catalysts were identified. Properties such as structure and basicity of the starting amides were demonstrated to influence the condensation process. Elemental iodine was used for the first time herein as an acid catalyst for the condensation of glyoxylic acid or its ester, which gave access to diaminoacetic acid derivatives in higher yields in most cases, as opposed to p-toluenesulfonic acid (PTSA). An abnormally high activity of mesyl amide when condensed with ethyl glyoxylate was noticed, which may evidence a special impact of the sulfonyl moiety in the amide molecule on the condensation.

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Oxaazatetracyclo[5.5.0.03, 10.05, 8]Dodecanes – a Promising Foundation for the Design of Thermally Stable, High-Density Energetic Compounds

Cited by 23 publications

References 32 publications

Pentacycloundecane (PCUD)‐Based Cage Frameworks as Potential Energetic Materials: Syntheses and Characterization

Pentacycloundecane (PCUD)‐Based Cage Frameworks as Potential Energetic Materials: Syntheses and Characterization

Design of Zero Oxygen Balance Energetic Materials on the Basis of Diels–Alder Chemistry

Synthesis of Diaminoacetic Acid Derivatives as a Promising Scaffold for the Synthesis of Polyheterocyclic Cage Compounds

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