Carbyne

Source: Wikipedia, the free encyclopedia.
This article is about the chemical compounds with a –C3• group. For the allotrope of carbon containing consecutive alkyne units, see linear acetylenic carbon. For other uses, see Carbyne (disambiguation).
Not to be confused with carbine, carbene, or carbone.
carbyne doublet configuration
doublet (1 radical, 1 pair, 1 vacant orbital)
carbyne quartet configuration
quartet (3 radicals)

In

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 chemical formula
can be written R−C· or R−C3· (also written as ⫶C−R), or just CH.

Carbynes can be seen as derivatives of the simplest such compound, the

unsubstituted carbyne H−C· or H−C3·, in which the functional group is a hydrogen
atom.

Reported for the first time back in 1967 by Kasatochkin, carbyne is an infinite sp1 hybridized long linear chain of carbon, where each link is just a single carbon atom.[2]

Electronic configuration

Carbyne molecules are generally found to be in electronic

isoelectronic with the nitrogen atom which does have three unpaired electrons in accordance with Hund's rule of maximum multiplicity. However the nitrogen atom has three degenerate
p orbitals, in contrast to the CH radical where hybridization of one orbital (the 3σ) leads to an energy difference.

Occurrence

A carbyne can occur as a short-lived reactive intermediate. For instance, fluoromethylidyne (CF) can be detected in the gas phase by spectroscopy as an intermediate in the flash photolysis of CHFBr2.[3]

Carbynes can act as trivalent

Lewis acid.[5]

References

Wikimedia Commons has media related to Carbyne.
  1. doi:10.1351/goldbook.C00854
  2. ^ KASATOCHKIN, VI; VV, KORSHAK; YP, KUDRYAVTSEV; AM, SLADKOV; IE, STERENBERG (1973). "ON CRYSTALLINE STRUCTURE OF CARBYNE". On Crystalline Structure of Carbyne.
  3. ^
    doi:10.1021/ja00346a072
    .
  4. doi:10.1002/anie.197305641
    .
  5. ^
    doi:10.1039/B002228O
    .
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