Cyanuric triazide

Cyanuric triazide
Names
	IUPAC name 2,4,6-Triazido-1,3,5-triazine
Identifiers
CAS Number	5637-83-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	20543;
PubChem CID	21857;
UNII	P5JCR9JM71 ;
CompTox Dashboard (EPA)	DTXSID40971806 ;
	InChI InChI=1S/C3N12/c4-13-10-1-7-2(11-14-5)9-3(8-1)12-15-6 Key: JKYMSKUDZIJFKI-UHFFFAOYSA-N; InChI=1/C3N12/c4-13-10-1-7-2(11-14-5)9-3(8-1)12-15-6 Key: JKYMSKUDZIJFKI-UHFFFAOYAS;
	SMILES C1(=NC(=NC(=N1)N=[N+]=[N-])N=[N+]=[N-])N=[N+]=[N-];
Properties
Chemical formula	C3N12
Molar mass	204.117 g·mol−1
Appearance	white crystal
Density	1.73 g·cm−3
Melting point	94 °C (201 °F; 367 K)
Boiling point	150 °C (302 °F; 423 K) Decomposition or explosion
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Explosive substance
Flash point
Autoignition; temperature	205 °C (401 °F; 478 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyanuric triazide (C₃N₁₂ or (NCN₃)₃) is described as an environmentally friendly, low toxicity, and organic primary explosive with a detonation velocity of about 7,300 m s⁻¹ and a autoignition temperature of 205 °C.

Structure

The cyanuric triazide molecule exists as a planar triskelion with molecular point group C_3h.^[3]^[4] The 1,3,5-triazine (or cyanuric) ring consists of alternating carbon and nitrogen atoms with C–N bond lengths of 1.334 to 1.336 Å. The distance from the center of the ring to each ring carbon atom is 1.286 Å, while the corresponding distance to ring nitrogens is 1.379 Å. Azide groups are linked to the carbon atoms on the cyanuric ring by single bonds with an interatomic distance of 1.399 Å.^[5]

Synthesis

Cyanuric triazide can be synthesized via the nucleophilic aromatic substitution of cyanuric trichloride with an excess of sodium azide in heated acetone. The white crystals can then be purified via recrystallization from −20 °C toluene.^[6]

Decomposition reactions

This white polycrystalline solid was found to be stable under standard conditions but is extremely shock sensitive causing it to violently decompose when ground with a mortar. The thermodynamic properties of cyanuric triazide were studied using bomb calorimetry with a combustion enthalpy (H) of 2234 kJ mol⁻¹ under oxidizing conditions and 740 kJ mol⁻¹ otherwise. The former value is comparable to the military explosive RDX, (C₃N₃)(NO₃)₃H₆, but is not put into use due to its less than favorable stability. Melting point examination showed a sharp melting range to clear liquid at 94–95 °C, gas evolution at 155 °C, orange to brown solution discoloration at 170 °C, orange-brown solidification at 200 °C and rapid decomposition at 240 °C. The rapid decomposition at 240 °C results from the formation of elemental carbon as graphite and the formation of nitrogen gas.^[6]

References

^ Haynes, W. M.; Lide, D. R. (2012). CRC Handbook of Chemistry and Physics 93rd Ed. CRC Press/Taylor and Francis. ISBN 978-1439880494.
^ Mikhail A. Ilyushin, Igor V. Tselinsky And Irina V. Shugalei (2012). "Environmentally Friendly Energetic Materials for Initiation Devices" (PDF). Central European Journal of Energetic Materials. 9 (4): 293–327.
^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 1291. ISBN 978-0-08-037941-8.
^ Housecroft, C. E.; Sharpe, A. G. (2008). Inorganic Chemistry (3rd ed.). Prentice Hall. pp. 94–99. ISBN 978-0-13-175553-6.
^ Keßenich, Elmar; Klapötke, Thomas M.; Knizek, Jörg; Nöth, Heinrich; Schulz, Axel (1998). "Characterization, Crystal Structure of 2,4-Bis(triphenylphosphanimino)tetrazolo[5,1-a]-[1,3,5]triazine, and Improved Crystal Structure of 2,4,6-Triazido-1,3,5-triazine". Eur. J. Inorg. Chem. 1998 (12): 2013–2016. doi:10.1002/(SICI)1099-0682(199812)1998:12<2013::AID-EJIC2013>3.0.CO;2-M.
^ ^a ^b Gillan, Edward G. (2000). "Synthesis of Nitrogen-Rich Carbon Nitride Networks from an Energetic Molecular Azide Precursor". Chemistry of Materials. 12 (12): 3906–3912. doi:10.1021/cm000570y.

[1] Haynes, W. M.; Lide, D. R. (2012). CRC Handbook of Chemistry and Physics 93rd Ed. CRC Press/Taylor and Francis. ISBN 978-1439880494.

[2] Mikhail A. Ilyushin, Igor V. Tselinsky And Irina V. Shugalei (2012). "Environmentally Friendly Energetic Materials for Initiation Devices" (PDF). Central European Journal of Energetic Materials. 9 (4): 293–327.

[3] Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 1291. ISBN 978-0-08-037941-8.

[4] Housecroft, C. E.; Sharpe, A. G. (2008). Inorganic Chemistry (3rd ed.). Prentice Hall. pp. 94–99. ISBN 978-0-13-175553-6.

[5] Keßenich, Elmar; Klapötke, Thomas M.; Knizek, Jörg; Nöth, Heinrich; Schulz, Axel (1998). "Characterization, Crystal Structure of 2,4-Bis(triphenylphosphanimino)tetrazolo[5,1-a]-[1,3,5]triazine, and Improved Crystal Structure of 2,4,6-Triazido-1,3,5-triazine". Eur. J. Inorg. Chem. 1998 (12): 2013–2016. doi:10.1002/(SICI)1099-0682(199812)1998:12<2013::AID-EJIC2013>3.0.CO;2-M.

[pubs-6] Gillan, Edward G. (2000). "Synthesis of Nitrogen-Rich Carbon Nitride Networks from an Energetic Molecular Azide Precursor". Chemistry of Materials. 12 (12): 3906–3912. doi:10.1021/cm000570y.

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