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- Title
Characterization of nitrogen-bridged 1,2,4,5-tetrazine-, furazan-, and 1 H-tetrazole-based polyheterocyclic compounds: heats of formation, thermal stability, and detonation properties.
- Authors
Wei, Tao; Wu, Jianzhang; Zhu, Weihua; Zhang, Chenchen; Xiao, Heming
- Abstract
The heats of formation (HOFs), thermal stability, and detonation properties for a series of nitrogen-bridged 1,2,4,5-tetrazine-, furazan-, and 1 H-tetrazole-based polyheterocyclic compounds (3,6-bis(1 H-1,2,3,4-tetrazole-5-ylamino)-1,2,4,5- tetrazine (TST), 3,6-bis(furazan-5-ylamino)-1,2,4,5-tetrazine (FSF), 3,4-bis(1,2,4,5- tetrazine-3-ylamino)-furazan (SFS), 3,4-bis(1 H-1,2,3,4-tetrazole-5-ylamino)-furazan (TFT), 1,5-bis(1,2,4,5-tetrazine-3-ylamino)-1H-1,2,3,4-tetrazole (STS), and 1,5-bis(furazan-3-ylamino)-1H-1,2,3,4-tetrazole (FTF) derivatives) were systematically studied by using density functional theory. The results show that the -N or -NHNH group plays a very important role in increasing the HOF values of the derivatives. Among these series, the SFS derivatives have lower energy gaps, while the TFT derivatives have higher ones. Incorporation of the -NH group into the FSF, SFS, STS, or FTF ring is favorable for enhancing its thermal stability, whereas the substitution of the -NHNH group could increase the thermal stability of the TST, SFS, STS, or FTF ring. The calculated detonation properties indicate that the -NO or -NF is very helpful for enhancing the detonation performance for these derivatives. Considering the detonation performance and thermal stability, six derivatives may be regarded as promising candidates of high-energy density materials (HEDMs). These results provide basic information for the molecular design of novel HEDMs.
- Subjects
TETRAZINE; TETRAZOLES; FURAZANS; NITROGEN; HETEROCYCLIC compounds; THERMAL analysis; DENSITY functionals; HEAT of formation
- Publication
Journal of Molecular Modeling, 2012, Vol 18, Issue 8, p3467
- ISSN
1610-2940
- Publication type
Article
- DOI
10.1007/s00894-012-1357-8