Challenging the Limitations of Tetranitro Biimidazole through Introducing a gem-Dinitromethyl Scaffold

Shangbiao Feng; Baoseng Zhang; Chunwang Luo; Yang Liu; Shuangfei Zhu; Ruijun Gou; Shuhai Zhang; Ping Yin; Siping Pang

doi:10.1021/acs.orglett.3c00149

Challenging the Limitations of Tetranitro Biimidazole through Introducing a gem-Dinitromethyl Scaffold

Shangbiao Feng^*
, Baoseng Zhang
, Chunwang Luo
, Yang Liu
, Shuangfei Zhu
, Ruijun Gou
, Shuhai Zhang^*
, Ping Yin^*
, Siping Pang

^*Corresponding author for this work

School of Material Science and Engineering

North University of China
Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

A gem-dinitromethyl group was successfully introduced into the TNBI·2H₂O structure (TNBI: 4,4′,5,5′-tetranitro-2,2′-bi-1H-imidazole) to obtain 1-(dinitromethyl)-4,4′,5,5′-tetranitro-1H,1′H-2,2′-biimidazole (DNM-TNBI). Benefiting from the transformation of an N-H proton into a gem-dinitromethyl group, the current limitations of TNBI were well solved. More importantly, DNM-TNBI has high density (1.92 g·cm^-3, 298 K), good oxygen balance (15.3%), and excellent detonation properties (D_v = 9102 m·s^-1, P = 37.6 GPa), suggesting that it has great potential as an oxidizer or a high-performance energetic material.

Original language	English
Pages (from-to)	1290-1294
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.3c00149
Publication status	Published - 3 Mar 2023

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title = "Challenging the Limitations of Tetranitro Biimidazole through Introducing a gem-Dinitromethyl Scaffold",

abstract = "A gem-dinitromethyl group was successfully introduced into the TNBI·2H2O structure (TNBI: 4,4′,5,5′-tetranitro-2,2′-bi-1H-imidazole) to obtain 1-(dinitromethyl)-4,4′,5,5′-tetranitro-1H,1′H-2,2′-biimidazole (DNM-TNBI). Benefiting from the transformation of an N-H proton into a gem-dinitromethyl group, the current limitations of TNBI were well solved. More importantly, DNM-TNBI has high density (1.92 g·cm-3, 298 K), good oxygen balance (15.3\%), and excellent detonation properties (Dv = 9102 m·s-1, P = 37.6 GPa), suggesting that it has great potential as an oxidizer or a high-performance energetic material.",

author = "Shangbiao Feng and Baoseng Zhang and Chunwang Luo and Yang Liu and Shuangfei Zhu and Ruijun Gou and Shuhai Zhang and Ping Yin and Siping Pang",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = mar,

day = "3",

doi = "10.1021/acs.orglett.3c00149",

language = "English",

volume = "25",

pages = "1290--1294",

journal = "Organic Letters",

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TY - JOUR

T1 - Challenging the Limitations of Tetranitro Biimidazole through Introducing a gem-Dinitromethyl Scaffold

AU - Feng, Shangbiao

AU - Zhang, Baoseng

AU - Luo, Chunwang

AU - Liu, Yang

AU - Zhu, Shuangfei

AU - Gou, Ruijun

AU - Zhang, Shuhai

AU - Yin, Ping

AU - Pang, Siping

PY - 2023/3/3

Y1 - 2023/3/3

N2 - A gem-dinitromethyl group was successfully introduced into the TNBI·2H2O structure (TNBI: 4,4′,5,5′-tetranitro-2,2′-bi-1H-imidazole) to obtain 1-(dinitromethyl)-4,4′,5,5′-tetranitro-1H,1′H-2,2′-biimidazole (DNM-TNBI). Benefiting from the transformation of an N-H proton into a gem-dinitromethyl group, the current limitations of TNBI were well solved. More importantly, DNM-TNBI has high density (1.92 g·cm-3, 298 K), good oxygen balance (15.3%), and excellent detonation properties (Dv = 9102 m·s-1, P = 37.6 GPa), suggesting that it has great potential as an oxidizer or a high-performance energetic material.

AB - A gem-dinitromethyl group was successfully introduced into the TNBI·2H2O structure (TNBI: 4,4′,5,5′-tetranitro-2,2′-bi-1H-imidazole) to obtain 1-(dinitromethyl)-4,4′,5,5′-tetranitro-1H,1′H-2,2′-biimidazole (DNM-TNBI). Benefiting from the transformation of an N-H proton into a gem-dinitromethyl group, the current limitations of TNBI were well solved. More importantly, DNM-TNBI has high density (1.92 g·cm-3, 298 K), good oxygen balance (15.3%), and excellent detonation properties (Dv = 9102 m·s-1, P = 37.6 GPa), suggesting that it has great potential as an oxidizer or a high-performance energetic material.

UR - https://www.scopus.com/pages/publications/85148669064

U2 - 10.1021/acs.orglett.3c00149

DO - 10.1021/acs.orglett.3c00149

M3 - Article

C2 - 36795059

AN - SCOPUS:85148669064

SN - 1523-7060

VL - 25

SP - 1290

EP - 1294

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Challenging the Limitations of Tetranitro Biimidazole through Introducing a gem-Dinitromethyl Scaffold

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