Research progress on design, synthesis and performance of energetic polynitro hexaazaisowurtzitane derivatives: Towards improved CL-20 analogues

Parakhin, V. V.; Smirnov, G. A.

doi:10.1016/j.fpc.2023.05.006

Cited by 8 publications

(5 citation statements)

References 131 publications

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“…Benzyl carbamate proved to be an active amide sufficiently stable towards acid hydrolysis and had the ability to engage in a condensation reaction with glyoxal under relatively low acidity conditions. For instance, in a relatively weak AcOH, the condensation between two benzyl carbamate molecules and two glyoxal molecules proceeded to yield a cyclic compound, N,N -bis(carbobenzoxy)-3,6-diamino-1,4-dioxane-2,5-diol (2). Increasing the acidity of the solvents by adding H 2 SO 4 to the reaction mixture allowed the activation of the condensation process and the preparation of products containing a greater quantity of secondary amido groups: N,N -bis(carbobenzoxy)ethan-1,2-diol (3), N,N ,N -tris(carbobenzoxy)ethanol (4) and N,N ,N ,N -tetrakis(carbobenzoxy)ethan (5).…”

Section: Discussionmentioning

confidence: 99%

“…The syntheses were effected for 20 h. Note: 1 In the pure form. 2 Mass content in the mixture. 3 Compound 1 was taken as 0.72 g.…”

Section: Entrymentioning

confidence: 99%

“…The search for and development of synthetic methods for new, more powerful highenergy-density materials (HEDMs) is a relevant objective for chemists and materials scientists worldwide [1][2][3][4][5][6][7][8][9][10][11][12][13]. One of the most actively developing directions in the synthesis of these substances is the synthesis of caged nitramines of aza-and oxaazaisowurtzitanes.…”

Section: Introductionmentioning

confidence: 99%

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Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Paromov

2023

Molecules

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The synthesis of substituted 2,4,6,8,10,12-hexaazaisowurtzitane via direct condensation is challenging. The selection of starting ammonia derivatives is very limited. The important step in developing alternative synthetic routes to these compounds is to investigate their formation process in detail. Here, we examined an acid-catalyzed condensation between benzyl carbamate and glyoxal in a ratio of 2:1 in a range of polar protic and aprotic solvents, and discovered a new process occurring during the cascade condensation of glyoxal with ammonia derivatives as well as discovered several processes hindering the formation of caged compounds. More specifically, a cyclic compound, N,N′-bis(carbobenzoxy)-3,6-diamino-1,4-dioxane-2,5-diol, was found to form at the early stage of condensation under low acidity conditions. The formation of this compound is governed by an easier condensation of alcohol groups compared to the amide ones. The condensation intermediates, N,N′-bis(carbobenzoxy)ethan-1,2-diol, N,N′,N″-tris(carbobenzoxy)ethanol, and N,N′,N″,N‴-tetrakis(carbobenzoxy)ethan, were obtained at a higher acidity. A range of solvents were identified: those that react with benzyl carbamate, those that promote the progress of side processes, and those that promote precipitation of condensation intermediates. A few byproducts were isolated and identified. It was found that DMSO exhibits a strong deactivating ability, while CH3CN exhibits a strong activating ability towards the acid-catalyzed condensation process of benzyl carbamate with glyoxal.

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Section: Discussionmentioning

confidence: 99%

“…The syntheses were effected for 20 h. Note: 1 In the pure form. 2 Mass content in the mixture. 3 Compound 1 was taken as 0.72 g.…”

Section: Entrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Paromov

2023

Molecules

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“…For instance, HMX molecules combined with DMF molecules mainly through four intermolecular hydrogen bonds in the HMX/DMF cocrystal. Molecules with H-donors and acceptors can easily form ECCs via forming hydrogen bonds [32]. The nitrogen atoms in the -NO 2 groups of CL-20 molecules can form intermolecular hydrogen bonds with the hydrogen atoms in -NH 2 groups of two nitroguanidine (NQ) molecules [33].…”

Section: Some Cl-20 Based Energetic Cocrystals -A Reviewmentioning

confidence: 99%

Some CL-20 based energetic cocrystals - A review

Türker

2024

EJCS

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There exists an inherent contradiction between the energy density and safety of energetic materials. To ameliorate and get an accord between energy and safety, cocrystallization seems to be a remedy which has been getting quite popular in the field of energetic materials. Energetic cocrystals represent one of the most important classes of research advances in the area of energetic materials. The cocrystallization significantly improves performance of energetic cocrystals, such as density, solubility, sensitivity, and thermal stability. This mini review summaries some of CL-20 based energetic cocrystals in terms of various aspects of them.

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“…NDOs are a highly unique and relatively underexplored functional group which possess high enthalpies of formation and high oxygen content. Accordingly, NDOs should be of interest to a variety of disciplines as they serve to address fundamental problems in energetic materials design and further the understanding of molecular stability in highly unique N/O group systems [ 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Nitrodiazene oxides: a unique nitrogen- and oxygen-containing functional group

Scherschel,

Piercey

2024

R. Soc. Open Sci.

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Nitrogen-/oxygen-containing functional groups (N/O groups) may be found in a wide variety of areas such as agriculture, drug design and energetic materials. Exploring the chemistry and synthesis of N/O groups is desirable as compounds containing their functionality may prove to be invaluable in a variety of fields. A unique N/O functional group which may offer additional insight into the design of high-heteroatom content systems is the 2-nitrodiazene-1- N -oxide group (NDO group). While unique on their own, NDOs combine the well-known azoxy (N(O)=N) and nitro (–NO 2 ) groups into a single unique N/O functional group. Although NDOs may offer superior densities and enthalpies of formations relative to their nitro counterparts, NDOs have been significantly less investigated than their nitro-bearing counterparts. This work will discuss NDOs in chemical literature from their initial discovery to modern synthesis techniques, energetic properties and chemical stability.

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Research progress on design, synthesis and performance of energetic polynitro hexaazaisowurtzitane derivatives: Towards improved CL-20 analogues

Cited by 8 publications

References 131 publications

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Some CL-20 based energetic cocrystals - A review

Nitrodiazene oxides: a unique nitrogen- and oxygen-containing functional group

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