Cyanocarbon

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In organic chemistry, cyanocarbons are a group of chemical compounds that contain several cyanide functional 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 group. [1] One of the simplest member is C(CN)4 (tetracyanomethane, also known as carbon tetracyanide). 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 can also stabilize 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]

Illustrative cyanocarbons:

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<span class="mw-page-title-main">Potassium ferricyanide</span> Chemical compound

Potassium ferricyanide is the chemical compound with the formula K3[Fe(CN)6]. This bright red salt contains the octahedrally coordinated [Fe(CN)6]3− ion. It is soluble in water and its solution shows some green-yellow fluorescence. It was discovered in 1822 by Leopold Gmelin.

<span class="mw-page-title-main">Hydrazone</span> Organic compounds - Hydrazones

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<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

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<span class="mw-page-title-main">Tetracyanoquinodimethane</span> Organic compound with formula C12H4N4

Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula (N≡C−)2C=C6H4=C(−C≡N)2. It is an orange crystalline solid. This cyanocarbon, a relative of para-quinone, is an electron acceptor that is used to prepare charge transfer salts, which are of interest in molecular electronics.

<span class="mw-page-title-main">Trimethylsilyl cyanide</span> Chemical compound

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:

<span class="mw-page-title-main">Zinc cyanide</span> Chemical compound

Zinc cyanide is the inorganic compound with the formula Zn(CN)2. It is a white solid that is used mainly for electroplating zinc but also has more specialized applications for the synthesis of organic compounds.

<span class="mw-page-title-main">Tetracyanoethylene</span> Organic compound with formula C2(CN)4

Tetracyanoethylene (TCNE) is organic compound with the formula C2(CN)4. It is a colorless solid, although samples are often off-white. It is an important member of the cyanocarbons.

<span class="mw-page-title-main">Benzyl cyanide</span> Chemical compound

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. It is also an important pheromone in certain species.

Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications:

References

  1. 1 2 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. doi : 10.1002/pola.10087
  2. Linn, W. J. (1969). "Tetracyanoethylene Oxide". Organic Syntheses . 49: 103. doi:10.15227/orgsyn.049.0103 .
  3. Middleton, W. J.; Wiley, D. W. (1961). "Tetramethylammonium 1,1,2,3,3-Pentacyanopropenide". Org. Synth. 41: 99. doi:10.15227/orgsyn.041.0099.