Synthesis and Characterization of 1‐Nitroguanyl‐3‐nitro‐5‐amino‐1,2,4‐triazole

Abstract

The synthesis of 1‐nitroguanyl‐3‐nitro‐5‐amino‐1,2,4‐triazole (ANTA‐NQ) (1) with good yield and high purity is described. DSC analysis showed that the material displays good thermal stability. An X‐ray crystallographic analysis confirms the structure of this material, as well as displays intramolecular hydrogen bonding. A gas pycnometry density for this material was measured to be 1.79 g cm−3. The heat of formation of this material was also measured. These data, along with the molecular formula were used as inputs to calculate the detonation velocity and detonation pressure using the Cheetah thermochemical code. The sensitivity of this material towards impact, spark and friction was also measured, as well as its vacuum thermal stability. The 3‐azido derivative 2 was also prepared and its properties are described as well. The above data show that (ANTA‐NQ) may be a high performing material with low sensitivity and good thermal stability.

Sensitivity of Energetic Materials: Theoretical Relationships to Detonation Performance and Molecular Structure

“…More interestingly, a small number of molecules lead to excellent trade-offs in spite of distinct explosophores. The most prominent example is ANTA-NQ, which was recently synthesized and put forward as a high-performing material with low sensitivity by Chavez et al 54 This compound exhibits a good combination of performance and sensitivity despite the presence of both N−NO 2 and C−NO 2 bonds. The reason for this remarkable stability is unclear.…”

Energetic Derivatives of Nitroguanidine – Synthesis and Properties

“…3,5-diamino-1-nitroguanyl-1,2,4-triazole, obtained by the method mentioned above, was used as a starting material in the synthesis described in [43]. The authors used the reactivity of the amino groups in positions 3 and 5 to replace one of them with the nitro (ANTA-NQ) or azide (AATA-NQ) group (Scheme 14).…”

3-Nitro-1-(2H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine (HANTT) and its energetic salts: highly thermally stable energetic materials with low sensitivity

“…All atoms of 2 are roughly coplanar, and the largest torsion angle is 169.55 (12) . This angle is located among N2-N1-C3-N6.…”

“…5 Researchers have reported several derivatives of ANTA in the past few years, which were synthesized either by modifying the original amino group to generate new energetic compounds, such as 3-nitro-5-nitramino-1H-1,2,4-triazole 6 and 5-azido-3-nitro-1H-1,2,4-triazole; 7 using a diazo bridge, such as 5,5 0 -dinitro-3,3 0 -azo-1,2,4-triazole (DNAT); 8 or with a direct C-N/N-N connection of energetic groups/compounds to triazole, such as 1,5-diamino-3-nitro-1,2,4-triazole (BANT), 9 4,6-bis-(3-amino-5-nitro-1H-1,2,4-triazole-1-yl)-5-nitropyrimidine (DANTNP), 10,11 and 1-nitroguanyl-3-nitro-5-amino-1,2,4-triazole (ANTA-NQ). 12 However, these derivatives more or less have some drawbacks. Decomposition temperatures of 3-nitro-5-nitramino-1H-1,2,4-triazole, 5-azido-3-nitro-1H-1,2,4-triazole and ANTA-NQ are 135 C, 174 C and 200 C, respectively, which are much lower than that of ANTA; whereas DNAT and DANTNP are less energetic than ANTA due to the moderate charge density of DNAT powder (d ¼ 1.67 g cm À3 ) 8 and the poor oxygen balance (À52.74%) and the lower energy of exothermic decomposition (reduced by approximately 324 J g À1 ) of DANTNP.…”