Quantum chemical study on nitroimidazole, polynitroimidazole and their methyl derivatives

Su, Xinxin; Cheng, Xinlu; Meng, Chuanmin; Yuan, Xiaoli

doi:10.1016/j.jhazmat.2008.03.135

Cited by 55 publications

(34 citation statements)

References 41 publications

(53 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…All of the predicted BDEs are listed in Table 4. The calculated BDE for C-NO 2 in MTNI (251 kJ mol −1 ) was found to be similar to the results predicted previously (255.6 kJ mol −1 ) by Su et al [36]. The BDEs for the C-NO 2 bonds of the aminopolynitroazole derivatives were found to be >236 kJ mol −1 , while those for N-NO 2 bonds were found to be >31 kJ mol −1 .…”

Section: Thermal Stabilitysupporting

confidence: 87%

See 1 more Smart Citation

Molecular design of aminopolynitroazole-based high-energy materials

et al. 2011

View full text Add to dashboard Cite

The density functional theory (DFT) was employed to calculate the energetic properties of several aminopolynitroazoles. The calculations were performed to study the effect of amino and nitro substituents on the heats of formation, densities, detonation performances, thermal stabilities, and sensitivity characteristics of azoles. DFT-B3LYP, DFT-B3PW91, and MP2 methods utilizing the basis sets 6-31 G* and 6-311 G (2df, 3p) were adopted to predict HOFs via designed isodesmic reactions. All of the designed aminopolynitroazoles had heats of formation of >220 kJ mol(-1). The crystal densities of the aminopolynitroazoles were predicted with the cvff force field. All of the energetic azoles had densities of >1.83 g/cm(3). The detonation velocities and pressures were evaluated using the Kamlet-Jacobs equations, utilizing the predicted densities and heats of formation. It was found that aminopolynitroazoles have a detonation velocity of about 9.1 km/s and detonation pressure of 36 GPa. The bond dissociation energies for the C-NO(2) and N-NO(2) bonds were analyzed to investigate the stabilities of the designed molecules. The charge on the nitro group was used to assess impact sensitivity in the present study. The results obtained imply that the designed molecules are stable and are expected to be candidates for high-energy materials (HEMs).

show abstract

Section: Thermal Stabilitysupporting

confidence: 87%

“…Calculated heats of formation for the aminopolynitroazole derivativesValues in parentheses are theoretically predicted from[36,37] …”

mentioning

confidence: 99%

Molecular design of aminopolynitroazole-based high-energy materials

et al. 2011

View full text Add to dashboard Cite

show abstract

“…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. Therefore, the article presented here mainly focuses on two series of explosive molecules, which have similar molecular structure.…”

Section: Introductionmentioning

confidence: 85%

“…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%

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

“…Attractive properties of 2,4(5)-1H-imidazole (8) readily available by from dinitroimidazole 1 prompted Su et al 81 to theoretical quantum calculations of several data concerning not only compounds 1 and 8 but also other nitroimidazoles and their methyl derivatives. Dinitroimidazole 8 is much less sensitive to impact and is a ca.…”

Section: Theoretical Quantum Calculations Of 14-dinitro-1h-imidazolementioning

confidence: 99%