Synthesis, characterization and quantum chemistry study of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine

doi:10.1007/s11458-009-0001-3

Front Chem Chin

2009, Vol. 4

Issue (1) : 69-74 https://doi.org/10.1007/s11458-009-0001-3

RESEARCH ARTICLE

Synthesis, characterization and quantum chemistry study of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine

Bozhou WANG(

), Weipeng LAI, Qian LIU, Peng LIAN, Yongqiang XUE

Xi′an Modern Chemistry Research Institute, Xi′an 710065, China

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Abstract

3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine (BTATz) was synthesized by the condensation of triaminoguanidinium nitrate with 2,4-pentanedione, followed by oxidation and substitution reaction. The product was characterized by elemental analysis, IR, NMR spectrometry and DSC analysis. Instead of nitrogen dioxide/N-methylpyrrolidone, acetic acid/sodium nitrite was used as the oxidizer during the oxidation. Thus, the cost was reduced and the process was simplified. The theoretical properties of BTATz were estimated by a B3LYP method based on a 6-31G(d,p) basis set, and the stable geometric configuration and bond order were obtained. The vibrational frequencies, IR spectrum and thermodynamic properties under different temperatures were obtained from vibrational analysis and the relationship between temperature and thermodynamics properties was deduced. Pyrolysis mechanism of BTATz was discussedand the transition state and activation energy of ring opening reaction of the tetrazole were deduced.

Keywords 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine (BTATz) synthesis theoretical calculation geometric configuration thermodynamics property pyrolysis mechanism

Corresponding Author(s): WANG Bozhou,Email:wbz600@163.com

Issue Date: 05 March 2009

Cite this article:

Yongqiang XUE,Bozhou WANG,Weipeng LAI, et al. Synthesis, characterization and quantum chemistry study of 3,6-bis(1H-1,2,3,4-tetrazol-5-yl-amino)-1,2,4,5-tetrazine[J]. Front Chem Chin, 2009, 4(1): 69-74.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-009-0001-3
https://academic.hep.com.cn/fcc/EN/Y2009/V4/I1/69

Fig.1

Tab.1 Comparison of the synthesis of from different oxidizers

Fig.2

Fig.3 The geometric configuration of BTATz after optimization at B3LYP/6-31G(d,p) level

Tab.2 The geometric parameters of BTATz after optimization at B3LYP/6-31G(d,p) level

Tab.3 The bond order of BTATz at B3LYP/6-31G(d,p) level

Tab.4 The vibrational frequencies (cm) and intensities (kJ?mol) of BTATz at B3LYP/6-31G (d,p) level

Tab.5 The thermodynamics properties of BTATz at different temperatures

Fig.4 The thermo-decomposition potential curves of ring-opening of BTATz

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