title: The search for tricyanomethane (cyanoform).
abstract: Although listed in organic chemistry textbooks as one of the strongest carbon acids, and in spite of more than a hundred years of attempts to prepare the compound, tricyanomethane (cyanoform) has resisted isolation and characterization, either as the carbon-acid 1 or as the dicyanoketenimine tautomer 2. Only in the vapor phase at very low pressure has the compound been identified from its microwave spectrum. Here we review and partially repeat the preparative work. With the aid of spectroscopic and diffraction methods (including powder diffraction) we have identified some of the products obtained as: hydronium tricyanomethanide (3), (Z)-3-amino-2-cyano-3-iminoacrylimide (4), a co-crystal of 4 with sulfuric acid (or corresponding iminium salt), and an addition product of 2 with hydrochloric acid (5/6). Quantum-mechanical calculations at the MP2/6-311++g(2d,2p) level have been made to assess the relative energies of some of the molecules involved.
authors.affiliation: Laboratory of Crystallography, ETH Zürich, Hönggerberg, HCI, 8093 Zurich, Switzerland.
authors.forename: Dubravka
authors.initials: D
authors.lastname: Sisak
authors.forename: Lynne B
authors.initials: LB
authors.lastname: McCusker
authors.forename: Andreas
authors.initials: A
authors.lastname: Buckl
authors.forename: Georg
authors.initials: G
authors.lastname: Wuitschik
authors.forename: Yi-Lin
authors.initials: YL
authors.lastname: Wu
authors.forename: W Bernd
authors.initials: WB
authors.lastname: Schweizer
authors.forename: Jack D
authors.initials: JD
authors.lastname: Dunitz