A CO2 Cloak for the Cyanide Dagger

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Science  04 Apr 2014:
Vol. 344, Issue 6179, pp. 45-46
DOI: 10.1126/science.1252466

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In the ever-expanding universe of compounds prepared to date, it is remarkable that a two-carbon ion with an apparently simple electronic structure could have eluded structural characterization until now. It is especially notable because this ion is formed from carbon dioxide (CO2) and cyanide (CN), each with a rich chemical history. On page 75 of this issue, Murphy et al. (1) report trapping the elusive cyanoformate ion as a crystalline salt with a bulky and unreactive cation. Their crystallographic and spectroscopic analysis along with quantum-mechanical calculations reveal a seemingly ordinary carbon-carbon (C−C) bond with the length of ∼1.5 Å, yet cyanoformate balances on the brink of fragmentation in nonpolar environments and its C−C bond breaks in more polar solvents.