Nitryl cyanide

Nitryl cyanide

Names
IUPAC name Nitroformonitrile
Other names Nitric cyanide
Identifiers
CAS Number	105879-05-8
3D model (JSmol)	Interactive image
PubChem CID	15798559
InChI InChI=1S/CN2O2/c2-1-3(4)5 Key: PLXPTFQGYWXIEA-UHFFFAOYSA-N
SMILES [O-][N+](=O)C#N
Properties
Chemical formula	CN2O2
Molar mass	72.023 g·mol−1
Appearance	Colourless liquid
Density	1.24 g ml−1 (−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 (ΔfH⦵298)	212 kJ mol−1
Related compounds
Related compounds	Nitrile isocyanide (CNNO2)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. ^{[1] [2]}

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. ^[1]

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. ^[1]

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.