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Cyanocarbon

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Cyanide Cyanocarbons Organic Stable

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In organic chemistry, cyanocarbons are a group of chemical compounds that contain several cyanide . Such substances generally are classified as , since they are formally derived from by replacing one or more hydrogen atoms with a cyanide group.Webster, Owen W. "Cyanocarbons: a classic example of discovery-driven research" Journal of Polymer Science, Part A: Polymer Chemistry 2001, volume, 40, pp. 210-221. One of the simplest member is (tetracyanomethane, also known as carbon tetracyanide). Organic chemists often refer to cyanides as .

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

Definition and examples

Cyanocarbons are organic compounds bearing enough cyano functional groups to significantly alter their chemical properties.

Illustrative cyanocarbons:

Tetracyanoethylene, which reduces to a stable anion C₂(CN)₄⁻, unlike most derivatives of ethylene.
Pentacyanocyclopentadiene, which forms an air-stable anion, in contrast to cyclopentadiene.
Tetracyanoethylene oxide, an electrophilic epoxide that undergoes ready scission of its C-C bond.
Tetracyanoquinodimethane, , which reduces to a stable anion, unlike most .
Cyanoform (tricyanomethane),
Pentacyanopropenide, .