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Nitryl cyanide

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Nitryl cyanide
Names
IUPAC name Nitroformonitrile
Other names Nitric cyanide
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
InChI
  • InChI=1S/CN2O2/c2-1-3(4)5Key: PLXPTFQGYWXIEA-UHFFFAOYSA-N
SMILES
  • (=O)C#N
Properties
Chemical formula CN2O2
Molar mass 72.023 g·mol
Appearance Colourless liquid
Density 1.24 g ml (−79 °C)
Melting point −85 °C (−121 °F; 188 K)
Boiling point 7 °C (45 °F; 280 K)
Solubility in water Reacts with water
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		212 kJ mol
Related compounds
Related compounds Nitrile isocyanide (CNNO2)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Nitryl cyanide is an energetic chemical compound with the formula NCNO2. Nitryl cyanide is a possible precursor to the theoretical explosive 2,4,6-trinitro-1,3,5-triazine.

Synthesis

Nitryl cyanide was first synthesized in 2014. The reaction of nitronium tetrafluoroborate with tert-butyldimethylsilyl cyanide at −30 °C produces nitryl cyanide, with tert-butyldimethylsilyl fluoride and boron trifluoride as byproducts.

NO2BF4 + t−BuMe2SiCN → NCNO2 + t−BuMe2SiF + BF3

The conversion of this method is only 50%, and using an excess of tert-butyldimethylsilyl causes the yield to drop even further.

References

  1. ^ Rahm, Martin; Bélanger-Chabot, Guillaume; Haiges, Ralf; Christe, Karl O. (2014-07-01). "Nitryl Cyanide, NCNO2". Angewandte Chemie International Edition. 53 (27): 6893–6897. doi:10.1002/anie.201404209. PMID 24861214.
  2. Zhou, Ming-Ming; Xiang, Dong (2022-05-29). "Theoretical Prediction of Structures and Properties of 2,4,6-Trinitro-1,3,5-Triazine (TNTA) Green Energetic Materials from DFT and ReaxFF Molecular Modeling". Materials. 15 (11): 3873. Bibcode:2022Mate...15.3873Z. doi:10.3390/ma15113873. ISSN 1996-1944. PMC 9182073. PMID 35683171.


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