Cyanocarbon

Cyanocarbons are a chemical compounds that contain several cyanide groups. Such substances generally are classified as organic compounds, since they are formally derived from hydrocarbons by replacing one or more hydrogen atoms with a cyanide. The parent member is C(CN)₄. Organic chemists often refer to cyanides as nitriles.

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In general, cyanide is an electronegative substituent. Thus, for example, cyanide-substituted carboxylic acids tend to be stronger than the parents. The cyanide group also stabilizes anions by delocalizing negative charge as revealed by resonance structures.

Definition and examples

“Cyanocarbons are organic compounds bearing enough cyano functional groups to significantly alter their chemical properties.”^[1]

Important cyanocarbons:

• tetracyanoethylene, which readily reduces to a stable anion, unlike most ethylene]] derivatives
• tricyanomethane, which forms a stable anion by ionization of the C-H bond.
• pentacyanocyclopentadiene, which is a strong acid
• tetracyanoethylene oxide, C₂(CN)₄O, an epoxide, undergoes readily scission of its C-C bond.
• tetracyanoquinodimethanide, C₆H₄-1,4-(C(CN)₂)₂, is a powerful electron acceptor.

References

1. ^ W. Webste, O. W. “Cyanocarbons: A Classic Example of Discovery-Driven Research” Journal of Polymer Science Part A: Polymer Chemistry 2001, Volume 40, Pages 210 - 221. DOI 10.1002/pola.10087