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

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

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