Theoretical study on a novel high-energy density material 4,6,10,12-tetranitro-5,11-bis(nitroimino)-2,8-dioxa-4,6,10,12-tetraaza-tricyclo[7,3,0,03,7]dodecane

Jin, Xinghui; Hu, Bingcheng; Lü, Wei; Gao, Sijing; Liu, Zuliang; Lv, Chen

doi:10.1039/c3ra46107f

Cited by 26 publications

(13 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Explosophores such as nitro (NO 2 ) and azide (N 3 ) functional groups are generally needed to sensitize energetic materials. X‐NO 2 (X = N,C,O) bonds substituted on energetic materials have been proposed to form “trigger bonds,” activated (i.e., more readily cleaved) bonds that break to initiate an explosive reaction .…”

Section: Introductionmentioning

confidence: 99%

Trigger bond analysis of nitroaromatic energetic materials using wiberg bond indices

Shoaf

Bayse

2018

J Comput Chem

View full text Add to dashboard Cite

The identification of trigger bonds, bonds that break to initiate explosive decomposition, using computational methods could help direct the development of novel, "green" and efficient high energy density materials (HEDMs). Comparing bond densities in energetic materials to reference molecules using Wiberg bond indices (WBIs) provides a relative scale for bond activation (%ΔWBIs) to assign trigger bonds in a set of 63 nitroaromatic conventional energetic molecules. Intramolecular hydrogen bonding interactions enhance contributions of resonance structures that strengthen, or deactivate, the CNO trigger bonds and reduce the sensitivity of nitroaniline-based HEDMs. In contrast, unidirectional hydrogen bonding in nitrophenols strengthens the bond to the hydrogen bond acceptor, but the phenol lone pairs repel and activate an adjacent nitro group. Steric effects, electron withdrawing groups and greater nitro dihedral angles also activate the CNO trigger bonds. %ΔWBIs indicate that nitro groups within an energetic molecule are not all necessarily equally activated to contribute to initiation. %ΔWBIs generally correlate well with impact sensitivity, especially for HEDMs with intramolecular hydrogen bonding, and are a better measure of trigger bond strength than bond dissociation energies (BDEs). However, the method is less effective for HEDMs with significant secondary effects in the solid state. Assignment of trigger bonds using %ΔWBIs could contribute to understanding the effect of intramolecular interactions on energetic properties. © 2018 Wiley Periodicals, Inc.

show abstract

Section: Introductionmentioning

confidence: 99%

Trigger bond analysis of nitroaromatic energetic materials using wiberg bond indices

Shoaf

Bayse

2018

J Comput Chem

View full text Add to dashboard Cite

show abstract

“…To achieve favorable oxygen balance, the traditional method is to introduce nitro groups, such as found in 2,4,6‐trinitrotoluene (TNT), 1,3,5‐trinitro‐1,3,5‐triazinane (RDX), and 1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocane (HMX). However, high energy density materials (HEDMs) with multiple nitro groups may pose danger to humans and the environment during both their synthesis and performance testing 5. New trends in the research and development of new energetics include two methods to improve oxygen balance, namely, introducing oxygen‐rich functional groups or heterocycles (e.g., furazan,6 N ‐oxide7), and eliminating unnecessary atoms 8…”

Section: Introductionmentioning

confidence: 99%

Energetic Salts Based on Furazan‐Functionalized Tetrazoles: Routes to Boost Energy

Wei

Zhang

et al. 2015

Chemistry A European J

View full text Add to dashboard Cite

Based on the backbone of the furazan-tetrazole structure, routes were developed to improve the properties of energetic materials. Two types of high-density energetic salts were designed, prepared, and fully characterized. Single-crystal X-ray analyses support the structural characteristics for two amino salts. A majority of the salts exhibited good detonation properties, high thermal stabilities, and relatively low impact and friction sensitivities. Hydroxylammonium and hydrazinium salts, 1-3 and 1-4, which have relatively high densities (1.84 and 1.74 g cm(-3,) , respectively), acceptable impact and friction sensitivities (14 J, 160 N and 28 J, 360 N), and good detonation pressures (38.3 and 32.2 GPa) and velocities (9323 and 9094 m s(-1) ), have performance properties superior to 1,3,5-trinitro-1,3,5-triazinane (RDX) and triaminotrinitrobenzene (TATB).

show abstract

“…During the last few decades, high-energy density compounds (HEDCs) with high positive heats of formation (HOFs), high densities (q), excellent detonation properties [detonation velocity (D) and detonation pressure (P)], good thermal stability as well as low impact, and shock sensitivities have been receiving considerable attention to meet the continuing development of national defense and economy [1][2][3][4][5]. Among various types of HEDMs, high energetic cyclic nitramines constitute a unique class of energetic materials and have played an important role in this field.…”

Section: Introductionmentioning

confidence: 99%

Theoretical studies on two novel series of energetic cyclic nitramines

Jin

Liu

2014

Struct Chem

Self Cite

View full text Add to dashboard Cite

Density functional theory calculations at the B3LYP/6-31G** theoretical level were performed for two series of guanidine-fused bicyclic skeleton derivatives (B-B7 and C-C7). The heats of formation (HOFs) were calculated via isodesmic reaction; the detonation properties were evaluated using the Kamlet-Jacobs equations; the bond dissociation energies were also analyzed to investigate the thermal stability of the cyclic nitramines. The results show that all the derivatives have high positive HOFs; compounds containing -N 3 groupshave the highest HOFs, while compounds containing -NF 2 groups have the highest density and detonation properties. Taking both of the detonation properties and thermal stabilities into consideration, compounds B1, B2, B5, C3, and C5 can be considered as the potential candidate of high-energy density compounds.

show abstract

Theoretical study on a novel high-energy density material 4,6,10,12-tetranitro-5,11-bis(nitroimino)-2,8-dioxa-4,6,10,12-tetraaza-tricyclo[7,3,0,03,7]dodecane

Cited by 26 publications

References 30 publications

Trigger bond analysis of nitroaromatic energetic materials using wiberg bond indices

Trigger bond analysis of nitroaromatic energetic materials using wiberg bond indices

Energetic Salts Based on Furazan‐Functionalized Tetrazoles: Routes to Boost Energy

Theoretical studies on two novel series of energetic cyclic nitramines

Contact Info

Product

Resources

About