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Angewandte Chemie - International Edition

Volumn 48, Issue 3, 2009, Pages 564-567

Energetic mono-, di-, and trisubstituted nitroiminotetrazoles

(2) Joo, Young Hyuk a Shreeve, Jean'ne M a

a UNIVERSITY OF IDAHO (United States)

Author keywords

Energetic materials; Explosives; Heats of formation; Nitrogen heterocycles; Tetrazoles

Indexed keywords

AMINES; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; NITRIC ACID; SPECTROSCOPIC ANALYSIS;

CHEMICAL EQUATIONS; DETONATION PRESSURES; ELEMENTAL ANALYSES; ENERGETIC MATERIALS; GOOD YIELDS; HEATS OF FORMATION; NITROGEN HETEROCYCLES; PRIMARY AMINES; SPECTROSCOPIC METHODS; TETRAZOLES; TITLE COMPOUNDS; X-RAY DIFFRACTIONS;

X RAY DIFFRACTION ANALYSIS;

EID: 58249137567 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200804755 Document Type: Article

Times cited : (152)

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- An alternate method with 70% HNO3 was also used for the synthesis of nitroiminotetrazoles 4 and 5. The reaction mixture was stirred for 3 days and then dried in air, and the white solid product was recrystallized from water. However, the products were obtained by this method in just 30-34% yield
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29
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- 3 (10 mL) at 0°C. The reaction mixture was stirred at ambient temperature for 18 h and then poured into ice water (20 g) and stirred for a further 3 h. The product was precipitated, filtered, washed with water, and dried in air at room temperature.
- 3 (10 mL) at 0°C. The reaction mixture was stirred at ambient temperature for 18 h and then poured into ice water (20 g) and stirred for a further 3 h. The product was precipitated, filtered, washed with water, and dried in air at room temperature.

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- Crystallographic data for 1: C3H6N 6O3: Mr, 174.14; crystal size: 0.88 x 0.48 x 0.34 mm3; triclinic, P1, a, 7.1095(13, b, 7.1116(13, c, 7.8928(15) Å, α, 89.235(2, β, 66.303(2, γ, 66.804(2)°, V, 330.86(11) Å3, Z, 2, 2θmax, 56.6°, ρcalcd, 1.748 mg m-3, μ, 0.153 mm-1, F(000, 180, R1, 0.0393 for 1475 observed (I > 2σI) reflections and 0.0419 for all 1616 reflections, goodness-of-fit, 1.065, 110 parameters. Crystallographic data for 4: C4H6N12O4: Mr, 286.21; crystal size: 0.25 x 0.12 x 0.11 mm3; monoclinic, P21/n, a, 8.182(3, b, 6.614(2, c, 10.463(3) Å, α, 90, β
- 1 = 0.0808 for 1124 observed (I > 2σI) reflections and 0.0868 for all 1265 reflections, goodness-of-fit = 1.228, 91 parameters. CCDC 703780 (1) and CCDC 703781 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif..

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- A portion of nitroiminotetrazoles 1-9 (20 mg) was subjected to a drop-hammer test, in which a 5 or 10 kg weight was dropped. For the categorization of impact sensitivities (insensitive: > 40 J; less sensitive: ≥ 35 J; sensitive: ≥ 4 J; very sensitive: ≤ 3 J), see: J. C. Galvez-Ruiz, G. Holl, K. Karaghiosoff, T. M. Klapötke, K. Loehnwitz, P. Mayer, H. Noeth, K. Polborn, C. J. Rohbogner, M. Suter, J. J. Weigand, Inorg. Chem. 2005, 44, 4237-4253.
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