Selective nitrosation of guanazine: preparation of azidoaminotriazole and nitrosoguanazine anion–Cu(II) complexes

Bichay, Magdy; Fronabarger, John W.; Gilardi, Richard; Butcher, Ray J.; Sanborn, William B.; Sitzmann, Michael E.; Williams, M. D.

doi:10.1016/j.tetlet.2006.06.177

Cited by 22 publications

(27 citation statements)

References 4 publications

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“…The C À N bond length in the ring lies in the range of 1.2977(18)-1.3825 ; the bond angles in the ring range from 102.79(11)-112.91(12)8. The bond lengths of N À N of the azido group, 1.2536 (17) and 1.1107 (17) , are close to those in 5-azido-3-amino-1,2,4triazole at 1.254(7) and 1.135 (8) , which shows that the inductive effect of the nitro group has become weaker at this position. Two types of intermolecular hydrogen bonds are observed as shown in Figure 1 www.chemeurj.org between N2 À H2 and O3B[N2…O3B, 2.8271 (14) ], N4 À H4 and O3 A[N4…O3 A, 2.8394 (14)].…”

Section: Resultsmentioning

confidence: 59%

“…Compound 1 was prepared by the selective nitration of guanazine, followed by heating at approximately 100 8C for 1 h. [17] As described in a patent, [16] 3-azido-N-nitro-1H-1,2,4triazol-5-amine (1) was prepared from 3-azido-5-amino-1,2,4-triazole by nitration of its nitric acid salt in 98 % sulfuric acid for a total yield of 43 %. In our hands, compound 1 was obtained in an 88 % yield by direct nitration of 3-azido-5-amino-1,2,4-triazole using a mixture of 98 % sulfuric and 70 % nitric acids.…”

Section: Resultsmentioning

confidence: 99%

“…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. The C À N bond length in the ring lies in the range of 1.2977(18)-1.3825 ; the bond angles in the ring range from 102.79(11)-112.91(12)8.…”

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: 59%

Section: Resultsmentioning

confidence: 99%

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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“…5-azido-3-amino-1,2,4-triazolium hydrochloride mono-hydrate (1.572 g cm -3 ). [26] The two independent chloride ligands are coordinated by six (Cl1) as well s four (Cl2) hydrogen atoms forming no regular polyhedron.…”

Section: Structuresmentioning

confidence: 99%

Synthesis and Characterization of 3,5‐Diamino‐1,2,4‐triazolium Dinitramide

Klapötke¹,

Martin²,

Mayr³

et al. 2010

Zeitschrift anorg allge chemie

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.3,5-Diamino-1,2,4-triazole (1, guanozol) was protonated with diluted hydrochloric acid, nitric acid, as well as perchloric acid forming 3,5-diamino-1,2,4-triazolium chloride hemihydrate (2), 3,5-diamino-1,2,4-triazolium nitrate (3) and 3,5-diamino-1,2,4-triazolium perchlorate (4), respectively. In a second step 4 was reacted with potassium dinitramide forming 3,5-diamino-1,2,4-triazolium dinitramide (5) and low soluble potassium perchlorate. 2-5 were characterized by low temperature single X-ray diffraction, IR and Raman as well as multinuclear NMR spectroscopy, mass spectrometry and differential scanning calorimetry.The heat of formation of 1-5 were calculated by the CBS-4M method to be 81.1 (1), 124.7 (2), -76.1 (3), -25.2 (4) and 138.7 (5) kJ mol -1 . With these values as well as the X-ray densities several detonation parameters were calculated using both computer codes EXPLO5.03 and EXPLO5.04. In addition, the sensitivities of 1-5 were determined by the BAM drophammer and friction tester as well as a small scale electrical discharge device.

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“…For the crystal structures of protonated C-amino-1,2,4-triazoles, see: Reck et al (1982); Lynch et al (1998Lynch et al ( , 1999; Baouab et al (2000); Bichay et al (2006); Guerfel et al (2007); Matulková et al (2007). For the crystal structure of 3,5diamino-1,2,4-triazole, see: Starova et al (1980).…”

Section: Related Literaturementioning

confidence: 99%

3,5-Diamino-1-phenyl-1,2,4-triazolium bromide

et al. 2010

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The title salt, C8H10N5 +·Br−, crystallizes with two independent structural units in the asymmetric unit. The two independent cations have different conformations, the triazole and phenyl rings forming dihedral angles of 32.57 (6) and 52.27 (7)°. In both cations, the amino groups are planar (the sum of the angles at the N atom of each amino group is 360°) and conjugated with the triazole ring. Intermolecular N—H⋯N and N—H⋯Br hydrogen bonds consolidate the crystal packing.

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Selective nitrosation of guanazine: preparation of azidoaminotriazole and nitrosoguanazine anion–Cu(II) complexes

Cited by 22 publications

References 4 publications

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

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

Synthesis and Characterization of 3,5‐Diamino‐1,2,4‐triazolium Dinitramide

3,5-Diamino-1-phenyl-1,2,4-triazolium bromide

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