Correlation between the bond dissociation energies and impact sensitivities in nitramine and polynitro benzoate molecules with polynitro alkyl groupings

Song, Xiao-Shu; Cheng, Xinlu; Yang, Xinling; Li, Dehua; Rong-Feng, Linghu

doi:10.1016/j.jhazmat.2007.04.105

Cited by 54 publications

(26 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is important to understand the pyrolysis mechanism of the compound [35][36][37]. The BDE of the molecule, corresponding to the enthalpy of reaction which is required for homolytic bond cleavage at 298 K and 1 atm, was evaluated [34,[38][39][40] by the following Equation 6:…”

Section: Methodsmentioning

confidence: 99%

“…It is well known that the Kamlet-Jacobs equations have been proved to be reliable and widely used to compute the detonation performance of energetic materials [35,36,44]. It can be seen from Table 5 Figure 5 displays the ρ, D and P values of the designed compounds, RDX and HMX, and it is easily seen that the detonation velocities and detonation pressures of M2-M7 are considerably increased when N→O oxidation bonds are incorporated into M1.…”

Section: Detonation Performance and Specific Impulsementioning

confidence: 98%

See 1 more Smart Citation

Computational Investigation on the Structure and Performance of Novel 4,7-Dinitro-furazano-[3,4-d]-pyridazine Derivatives

Wang¹,

Yuan²,

Liu³

et al. 2017

Cent. Eur. J. Energ. Mater.

View full text Add to dashboard Cite

Seven novel energetic 4,7-dinitro-furazano-[3,4-d]-pyridazine derivatives were designed, and their optimized structures and performances were studied by density functional theory (DFT) at B3LYP/6-311g(d,p) level. The detonation performances were estimated by the Kamlet-Jacobs equations. The results show that these compounds have high crystal densities (1.818-1.925 g·cm , and some of them exhibit higher BDEs than that of RDX (N-NO2 bond, 149.654 kJ·mol , 39.00 GPa). Otherwise, the specific impulse values of M1-M7 (266-279 s) outperform HMX (266 s) by 0-13 s, which indicates that M1-M7 may show better performance as monopropellants. It is concluded that density, heat of formation, stability, detonation performance and specific impulse of the designed compounds depend on the position and number of the N→O oxidation bonds.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Detonation Performance and Specific Impulsementioning

confidence: 98%

Computational Investigation on the Structure and Performance of Novel 4,7-Dinitro-furazano-[3,4-d]-pyridazine Derivatives

Wang¹,

Yuan²,

Liu³

et al. 2017

Cent. Eur. J. Energ. Mater.

View full text Add to dashboard Cite

show abstract

“…Therefore, the article presented here mainly focuses on two series of explosive molecules, which have similar molecular structure. In order to see whether the conclusion obtained by references [24,25] is general for the title compounds, we investigate the weakest BDE scaled by the molecular total energy and the results of the present research will be herein.…”

Section: Introductionmentioning

confidence: 93%

“…These detailed theoretical studies indicated that in those energetic materials which have similar molecular structure, the relationship between the sensitivity and the molecular structure may be easily found. Recently, Song et al [24,25] substantiated a nearly linear correlation between the impact sensitivity and the ratio of the BDE value to the molecular total energy in a certain class of explosives. Su and coworkers [26] also observed a good relationship between the ratio of the BDE value to the molecular total energy and the impact sensitivity in nitroimidazole type compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Researchers' study [4,17] showed that the rupture of this bond is the first step in decomposition process. The chemical stabilities and impact sensitivities of energetic materials have recently been related to the strengths of the weakest bond R-NO 2 , which may be obtained by calculating the BDE [18][19][20][21][22][23][24][25][26]. Rice and his coworkers [7] pointed out that there was a rough correlation between the logarithm of the impact sensitivity and the weakest BDE for some nitroaromatic molecules.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Investigation of correlation between impact sensitivities and bond dissociation energies in some triazole energetic compounds

Zhao

Cheng

2010

Struct Chem

View full text Add to dashboard Cite

In this article, density functional theory has been utilized to study on the correlation between impact sensitivities h 50% and the bond dissociation energies (BDEs) of nine triazole energetic explosives. By employing B3LYP and B3P86 method with the 6-311G** basis set, all the molecules have been fully optimized. The BDEs for removal of the NO 2 group in these compounds have also been calculated at the same level. Computed results show that BDEs calculated by B3LYP method are all less than those by B3P86 method. The relationship between the impact sensitivities and the weakest C-NO 2 bond dissociation energy (BDE) values have been investigated.The results indicate a good linear correlation between the impact sensitivity h 50% and the ratio (BDE/E) of the weakest BDE to the total energy E.

show abstract

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

Correlation between the bond dissociation energies and impact sensitivities in nitramine and polynitro benzoate molecules with polynitro alkyl groupings

Cited by 54 publications

References 26 publications

Computational Investigation on the Structure and Performance of Novel 4,7-Dinitro-furazano-[3,4-d]-pyridazine Derivatives

Computational Investigation on the Structure and Performance of Novel 4,7-Dinitro-furazano-[3,4-d]-pyridazine Derivatives

Investigation of correlation between impact sensitivities and bond dissociation energies in some triazole energetic compounds

Trigger bond analysis of nitroaromatic energetic materials using wiberg bond indices

Contact Info

Product

Resources

About