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Chemists Finally Nab Nitryl Cyanide

High-energy-density molecule has promise as an explosive and could be an interstellar molecule to boot

by Elizabeth K. Wilson
June 9, 2014 | A version of this story appeared in Volume 92, Issue 23

Credit: Angew. Chem. Int. Ed.
Structure and data for NCCO2
Credit: Angew. Chem. Int. Ed.

Nitryl cyanide, N≡CNO2, looks energetic and relatively simple on paper. Computational models have long suggested it’s a potentially useful high-energy-density compound. It could also play a role in atmospheric and interstellar chemistry. But the molecule is so reactive that nobody has managed to prepare, isolate, and characterize it—until now. After much investigation, Martin Rahm and Karl O. Christe of the University of Southern California and colleagues found that the reaction of NO2BF4 with R´R2SiC≡N (R´ = tert-butyl, R = methyl) in nitromethane—performed under carefully controlled temperature and concentration—allowed them to produce N≡CNO2 in 50% yield (Angew. Chem. Int. Ed. 2014, DOI: 10.1002/anie.201404209). The vibrational spectra of N≡CNO2, which is a stable gas at room temperature, agreed with predicted spectra. The compound’s potential, not only as a rocket propellant but also as a building block for other energetic materials, should prompt much new investigation, the researchers say. They also note that N≡CNO2 resembles other nitriles observed in interstellar space and could be a target for astronomers to pursue.


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