Carbyne

In organic chemistry, a carbyne is a general term for any compound whose structure consists of an electrically neutral carbon atom connected by a single covalent bond and has three non-bonded electrons.

[1] The carbon atom has either one or three unpaired electrons, depending on its excitation state; making it a radical.

The CH radical is in fact isoelectronic with the nitrogen atom which does have three unpaired electrons in accordance with Hund's rule of maximum multiplicity.

For instance, fluoromethylidyne (CF) can be detected in the gas phase by spectroscopy as an intermediate in the flash photolysis of CHFBr2.

[5] Such a compound can be obtained by the reaction of tungsten hexacarbonyl W(CO)6 with lithium diisopropylamide to form (iPr2N)(OLi)C=W(CO)5.