Unraveling the reactivity of the azo bridge in 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate in the synthesis of energetic compounds

Peng Chen; Lili Qiu; Ping Yin; Chunlin He; Siping Pang; Jean’ne M. Shreeve

doi:10.1039/D2CC00215A

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Unraveling the reactivity of the azo bridge in 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate in the synthesis of energetic compounds†

Peng Chen,

‡^ab Lili Qiu,‡^ab Ping Yin,

^ab Chunlin He,

*^abc Siping Pang

*^b and Jean’ne M. Shreeve

*^c

Author affiliations

* Corresponding authors

^a Experimental Center of Advanced Materials, School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 10081, China
E-mail: chunlinhe@bit.edu.cn

^b School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 10081, China
E-mail: pangsp@bit.edu.cn

^c Department of Chemistry, University of Idaho, Moscow, Idaho, USA
E-mail: jshreeve@uidaho.edu

Abstract

The introduction of an azo bridge into an energetic compound is an efficient strategy to improve its nitrogen content, heat of formation and detonation performances. 3,3′-(5-Methyl dinitroacetate-1,2,4-oxadiazolyl)-4,4′-azofurazan exhibits unusual reactivity with several bases while preparing its corresponding azo bridged energetic salts. These interesting phenomena were explained by both experimental and theoretical calculations with Gaussian 09. The physical and chemical properties of three energetic salts were evaluated. These materials exhibit high densities, excellent detonation properties and acceptable sensitivities.

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DOI: https://doi.org/10.1039/D2CC00215A
Article type: Communication
Submitted: 12 Jan 2022
Accepted: 01 Feb 2022
First published: 01 Feb 2022

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Chem. Commun., 2022,58, 2874-2877

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Unraveling the reactivity of the azo bridge in 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate in the synthesis of energetic compounds

P. Chen, L. Qiu, P. Yin, C. He, S. Pang and J. M. Shreeve, Chem. Commun., 2022, 58, 2874 DOI: 10.1039/D2CC00215A

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Chemical Communications

Unraveling the reactivity of the azo bridge in 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate in the synthesis of energetic compounds†

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Unraveling the reactivity of the azo bridge in 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate in the synthesis of energetic compounds

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