2,4,4,8,8‐Pentanitro‐2‐Azaadamantane: A High‐Density Energetic Compound

Hou, Tianjiao; Ruan, Hongwei; Wang, Guixiang; Luo, Jun

doi:10.1002/ejoc.201701403

Cited by 12 publications

(5 citation statements)

References 35 publications

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“…In 2017, Luo et al reported synthesis of high-density energetic compound nitramine 75 (scheme 13). [28] Adamantane diketone 73 was derivatized to dihydrazone, then treated with LDA (lithium diisopropylamide). It should be noted that authors referred this reaction as Bamford-Stevens Thus far, we discussed applications of Bamford-Stevens reaction in various areas of chemistry.…”

Section: Total Synthesismentioning

confidence: 99%

Bamford‐Stevens and Shapiro Reactions in Organic Synthesis

Ghavre¹

2020

Asian J Org Chem

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Total synthesis of natural products often requires installation of double bond without adding carbon. Bamford-Stevens and Shapiro reactions offer an option to execute such transformation. Several developments have been made in these reactions and their applications in a diverse area of chemistry. Lack of a dedicated review on these reactions in the recent time is hampering an access to collective information and a critical analysis of the new developments. This minireview highlights methodological developments and applications of Bamford-Stevens and Shapiro reactions in organic synthesis published in the past ten years.

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Section: Total Synthesismentioning

confidence: 99%

Bamford‐Stevens and Shapiro Reactions in Organic Synthesis

Ghavre¹

2020

Asian J Org Chem

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“…We studied several representative caged polynitroamino energetic compounds, including CL-20, TEX, and ONC. Additionally, for the sake of completeness, we also considered representative polynitro species containing gem-dinitro groups, viz., 2,2,4,4,6,6-hexanitroadamantane (HNA, 4 , Chart ), , and two very recently reported nitramino derivatives: 2,4,4,8,8-pentanitro-2-azaadamantane ( 5 ) and 2,4,4,6,8,8-hexanitro-2,6-diazaadamantane (HNDAA, 6 ) containing mixed dintro- and nitroamino functionalities. , Ultimately, we considered the radical and molecular primary decomposition reactions of all species studied at the DLPNO-CCSD(T)/jun-cc-pVQZ level of theory and obtained the most accurate values of bond energies and activation barriers of molecular channels among those reported up to date.…”

Section: Introductionmentioning

confidence: 99%

Accurate Prediction of Bond Dissociation Energies and Barrier Heights for High-Energy Caged Nitro and Nitroamino Compounds Using a Coupled Cluster Theory

Kiselev

Goldsmith

2019

J. Phys. Chem. A

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Highly accurate theoretical values of bond energies and activation barriers of primary decomposition reactions are crucial for reliable predictions of thermal decomposition and detonation-related phenomena of energetic materials (EM). However, due to the prohibitive computational cost, high-level ab initio calculations had been impractical for a large number of important EMs, including, e.g., hexanitrohexaazaisowurtzitane (CL-20). In the present work, we obtained accurate bond dissociation energies and the activation barriers for primary decomposition reactions for a series of novel promising caged polynitroamino and polynitro EMs, viz., CL-20, TEX, octanitrocubane (ONC), and hexanitro derivatives of adamantane, using the recently proposed domain-localized pair natural orbitals (DLPNO) modifications of coupled cluster techniques. DLPNO-CCSD(T) allows for routine quadruple-ζ basis set quality coupled cluster calculations for the species comprised of ∼30 non-H atoms. The benchmarks on a number of simpler congeners of CL-20 and ONC revealed that the DLPNO approach does not deteriorate the quality of the quadruple-ζ coupled cluster procedure. With the aid of this technique, the full set of gas-phase primary decomposition reactions for all 9 conformers of CL-20 was considered. For all species studied, C−NO 2 or N−NO 2 radical decomposition channels dominate over molecular counterparts. The best theoretical results reported in the literature so far, viz., density functional theory energies of nitro group radical elimination in CL-20 and ONC, underestimate the value by ∼10 kcal mol −1 . We also present reliable and accurate gas-phase formation enthalpies for CL-20, ONC, and related species. In a more general sense, these results offer a new level of predictive computational kinetics for polynitro-caged energetic materials.

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“…3,5,7-trinitro-1-azaadamantane 19 and 2,4,10-trinitro-2,4,10-triazaadamantane. 7 In recent years, our group has made breakthroughs in the field of polynitroazaadamantanes, such as 2,4,9-trinitro-2,4,9-triazaadamantane-7-yl nitrate, 20 2,4,4,8,8-pentanitro-2-azaadamantane ( PNAA ), 21 and 2,4,4,6,8,8-hexanitro-2,6-diazaadamantane (HNDAA). 22 However, only one series of polynitrooxaadamantanes, namely 4,4,8,8-tetranitro-2-oxaadamantane, 23 has been reported.…”

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confidence: 99%