Cyanocarbon

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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.

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.

[edit] 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.

[edit] 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