Tricyanomethane and Its Ketenimine Tautomer: Generation from Different Precursors and Analysis in Solution, Argon Matrix, and as a Single Crystal

Angewandte Chemie
Klaus BanertHeinrich Lang

Abstract

Solutions of azidomethylidenemalononitrile were photolyzed at low temperatures to produce the corresponding 2H-azirine and tricyanomethane, which were analyzed by low-temperature NMR spectroscopy. The latter product was also observed after short thermolysis of the azide precursor in solution whereas irradiation of the azide isolated in an argon matrix did not lead to tricyanomethane, but to unequivocal detection of the tautomeric ketenimine by IR spectroscopy for the first time. When the long-known "aquoethereal" greenish phase generated from potassium tricyanomethanide, dilute sulfuric acid, and diethyl ether was rapidly evaporated and sublimed, a mixture of hydronium tricyanomethanide and tricyanomethane was formed instead of the previously claimed ketenimine tautomer. Under special conditions of sublimation, single crystals of tricyanomethane could be isolated, which enabled the analysis of the molecular structure by X-ray diffraction.

References

Feb 16, 2002·The Journal of Organic Chemistry·Justin FinnertyCurt Wentrup
May 19, 2010·Chemistry : a European Journal·Dubravka SisakJack D Dunitz
Dec 21, 2010·The Journal of Organic Chemistry·Agnes KüttIvo Leito
Mar 4, 2015·Organic & Biomolecular Chemistry·Bao Hu, Stephen G DiMagno
Sep 19, 2015·Angewandte Chemie·Theresa SoltnerAndreas J Kornath
Apr 14, 2016·Chemistry Central Journal·Shaaban A Elroby
Jan 1, 1996·Journal of Research of the National Institute of Standards and Technology·David G Watson

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