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.
YouTube Encyclopedic
-
1/3Views:505302662
-
Organic Chemistry II CHEM-2425 Ch 19 Carboxylic Acids and Nitriles Part 1
-
Organic Chemistry II CHEM-2425 Ch 19 Carboxylic Acids and Nitriles Part 3
-
34.04 Site Selectivity in Electrophilic Aromatic Substitution
Transcription
Definition and examples
Cyanocarbons are organic compounds bearing enough cyano functional groups to significantly alter their chemical properties.[1]
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.[2]
- Tetracyanoquinodimethane, C6H4-para-(C(CN)2)2, which reduces to a stable anion, unlike most quinones.
- Cyanoform (tricyanomethane), HC(CN)3
- Pentacyanopropenide, [(NC)2C=C(CN)−C(CN)2]−.[3]
References
- ^ a b 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
- ^ Linn, W. J. (1969). "Tetracyanoethylene Oxide". Organic Syntheses. 49: 103. doi:10.15227/orgsyn.049.0103.
- ^ Middleton, W. J.; Wiley, D. W. (1961). "Tetramethylammonium 1,1,2,3,3-Pentacyanopropenide". Org. Synth. 41: 99. doi:10.15227/orgsyn.041.0099.
 | This article about an organic compound is a stub. You can help Wikipedia by expanding it. |
This page was last edited on 3 November 2023, at 02:43