Nitroimines: II. Structure of Nitroamino-1,2,4-triazoles

Astakhov, A. M.; Vasil’ev, A. D.; Мolokeev, Maxim S.; Revenko, V. A.; Stepanov, R. S.

doi:10.1007/s11178-005-0265-0

Cited by 18 publications

(17 citation statements)

References 27 publications

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“…The X-ray crystallographic analysis data for 1 showed that it crystallizes in the orthorhombic space group P212121 with a density of 1.795 mg m À13 . All atoms are nearly coplanar with the largest torsion angle of 5.64 (18)8 between C3-N3A-N3B-O3B. Similar to other nitroaminotriazoles, for example, 3-nitroamino-1,2,4-triazole, [18] 4-nitroamino-1,2,4-triazole, and 1-nitroanimo-1,2,3-triazole, [14] the NÀH bond lengths on the ring are the same at 0.8600 which is shorter than the N À H bond length 0.880(7) of 5-azido-3-amino-1,2,4-triazole.…”

Section: Resultsmentioning

confidence: 99%

“…All atoms are nearly coplanar with the largest torsion angle of 5.64 (18)8 between C3-N3A-N3B-O3B. Similar to other nitroaminotriazoles, for example, 3-nitroamino-1,2,4-triazole, [18] 4-nitroamino-1,2,4-triazole, and 1-nitroanimo-1,2,3-triazole, [14] the NÀH bond lengths on the ring are the same at 0.8600 which is shorter than the N À H bond length 0.880(7) of 5-azido-3-amino-1,2,4-triazole. [17] This may be caused by the strong electron-withdrawing inductive effects of the nitro group.…”

Section: Resultsmentioning

confidence: 99%

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3‐Azido‐N‐nitro‐1H‐1,2,4‐triazol‐5‐amine‐Based Energetic Salts

Wang

Parrish

Shreeve

2011

Chemistry A European J

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Twelve energetic nitrogen-rich salts based on 3-azido-N-nitro-1H-1,2,4-triazol-5-amine were prepared and fully characterized by (1)H, (13)C NMR, and IR spectroscopy, differential scanning calorimetry (DSC), and elemental analysis. The crystal structures of the neutral compound 3-azido-N-nitro-1H-1,2,4-triazole-5-amine (1) and its triaminoguanidinium salt (13) were determined by single-crystal X-ray diffraction. The density of 1 and its twelve salts ranged from 1.57 to 1.79 g cm(-3), and the heat of formation was calculated with the Gaussian 03 suite of programs. Compounds 1-13 exhibit promising detonation performances (pressure: 25.3-39.3 GPa; velocity: 8159-9409 m s(-1); EXPLO 5.05). Impact sensitivities were also determined by hammer tests and resulted ranging from 2.5 J (very sensitive) to >40 J (insensitive).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

3‐Azido‐N‐nitro‐1H‐1,2,4‐triazol‐5‐amine‐Based Energetic Salts

Wang

Parrish

Shreeve

2011

Chemistry A European J

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“…The nomenclature of 5-(nitroamino)tetrazoles, also referred to as (nitramino)-or (nitrimino)tetrazoles, is usually inconsistent in literature [7], as a result of incomplete characterization of the previously reported compounds. Therefore, a complete characterization of three well-known (nitro-amino)tetrazoles is given in this work.…”

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confidence: 99%

Nitration Products of 5‐Amino‐1H‐tetrazole and Methyl‐5‐amino‐1H‐tetrazoles – Structures and Properties of Promising Energetic Materials

Klapötke

Stierstorfer

2007

Helvetica Chimica Acta

126

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The nitration of 5-amino-1H-tetrazole (1), 5-amino-1-methyl-1H-tetrazole (3), and 5-amino-2-methyl-2H-tetrazole (4) with HNO 3 (100%) was undertaken, and the corresponding products 5-(nitrimino)-1H-tetrazole (2), 1-methyl-5-(nitrimino)-1H-tetrazole (5), and 2-methyl-5-(nitramino)-2H-tetrazole (6) were characterized comprehensively using vibrational (IR and Raman) spectroscopy, multinuclear ( 1 H, 13C, 14 N, and 15 N) NMR spectroscopy, mass spectrometry, and elemental analysis. The molecular structures in the crystalline state were determined by single-crystal X-ray diffraction. The thermodynamic properties and thermal behavior were investigated by using differential scanning calorimetry (DSC), and the heats of formation were determined by bomb calorimetric measurements. Compounds 2, 5, and 6 were all found to be endothermic compounds. The thermal decompositions were investigated by gas-phase IR spectroscopy as well as DSC experiments. The heats of explosion, the detonation pressures, and velocities were calculated with the software EXPLO5, whereby the calculated values are similar to those of common explosives such as TNT and RDX. In addition, the sensitivities were tested by BAM methods (drophammer and friction) and correlated to the calculated electrostatic potentials. The explosion performance of 5 was investigated by Koenen steel sleeve test, whereby a higher explosion power compared to RDX was reached. Finally, the long-term stabilities at higher temperatures were tested by thermal safety calorimetry (FlexyTSC). X-Ray crystallography of monoclinic 2 and 6, and orthorhombic 5 was performed.

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“…2. The double C]NNO 2 bond in compound 4-02 (as well as in other nitroimines for which X-ray diffraction data are available 17 ) appears to be a double bond which consists with precursor 1-3 but differs from guadipyr. In addition, there is intramolecular hydrogen bond present in compound 4-02.…”

Section: Synthesismentioning

confidence: 98%