AskDefine | Define carbonyl

Dictionary Definition

carbonyl adj : relating to or containing the carbonyl group [syn: carbonylic] n : a compound containing metal combined with carbon monoxide

User Contributed Dictionary

English

Noun

  1. In organic chemistry, a divalent functional group, (-CO-), characteristic of aldehydes, ketones, carboxylic acids, amides, carboxylic acid anhydrides, carbonyl halides, esters and others.
  2. Any compound of a metal with carbon monoxide, such as nickel carbonyl, Ni(CO)4.
functional group -CO-
any compound of a metal with carbon monoxide

Extensive Definition

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O.
The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl); in this situation, carbon is triple-bonded to oxygen : C≡O.
The remainder of this article concerns itself with the organic chemistry definition of carbonyl.

Carbonyl compounds

A carbonyl group characterizes the following types of compounds (where -CO denotes a C=O carbonyl group):
Other organic carbonyls are urea and carbamates. Examples of inorganic carbonyl compounds are carbon dioxide, carbonyl sulfide and phosgene

Reactivity

Oxygen is more electronegative than carbon, and thus pulls electron density away from carbon to increase the bond's polarity. Therefore, the carbonyl carbon becomes electrophilic, and thus more reactive with nucleophiles. Also, the electronegative oxygen can react with an electrophile; for example a proton in an acidic solution or other Lewis Acid.'''
The alpha hydrogen in a carbonyl compound is much more acidic (~1030 times more acidic) than a typical CH bond. For example the pKa values of acetaldehyde and acetone are 16.7 and 19, respectively.
Amides are the most stable of the carbonyl couplings due to their high resonance stabilization between the Nitrogen-Carbon and Carbon-Oxygen bonds.
Carbonyl groups can be reduced by reaction with hydride reagents such as NaBH4 and LiAlH4, and by organometallic reagents such as organolithium reagents and Grignard reagents.
Other important reactions include:

α,β-Unsaturated carbonyl compounds

α,β-Unsaturated carbonyl compounds are an important class of carbonyl compounds with the general structure Cβ=Cα−C=O. In these compounds the carbonyl group is conjugated with an alkene (hence the adjective unsaturated), from which they derive special properties. Examples of unsaturated carbonyls are acrolein, mesityl oxide, acrylic acid and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction. The carbonyl group, be it an aldehyde or acid or a ketone, draws electrons away from the alkene and the alkene group in unsaturated carbonyls are therefore deactived towards an electrophile such as bromine or hydrochloric acid. As a general rule with unsymmetric electrophiles hydrogen attaches itself at the α position in an electrophilic addition. On the other hand, these compounds are activated towards nucleophiles in nucleophilic addition.

Spectroscopy

  • Infrared spectroscopy: the C=O double bond absorbs infrared light at wavenumbers between approximately 1600–1900 cm−1. The exact location of the absorption is well understood with respect to the geometry of the molecule. This absorption is known as the "carbonyl stretch" when displayed on an infrared absorption spectrum.
  • Nuclear magnetic resonance: the C=O double-bond exhibits different resonances depending on surrounding atoms, generally a downfield shift. The 13C NMR of a carbonyl carbon is in the range of 160-220 ppm.

References

Further reading

carbonyl in Catalan: Carbonil
carbonyl in Czech: Karbonylové sloučeniny
carbonyl in Danish: Carbonylgruppe
carbonyl in German: Carbonylgruppe
carbonyl in Estonian: Karbonüülrühm
carbonyl in Spanish: Grupo carbonilo
carbonyl in Esperanto: Karbonila grupo
carbonyl in French: Composé carbonylé
carbonyl in Korean: 카보닐기
carbonyl in Italian: Carbonile
carbonyl in Hebrew: קרבוניל
carbonyl in Dutch: Carbonylgroep
carbonyl in Japanese: カルボニル基
carbonyl in Norwegian: Karbonyl
carbonyl in Polish: Grupa karbonylowa
carbonyl in Portuguese: Carbonila
carbonyl in Russian: Карбонильная группа
carbonyl in Slovak: Karbonylová skupina
carbonyl in Finnish: Karbonyyli
carbonyl in Turkish: Karbonil grubu
carbonyl in Ukrainian: Карбонільна група
carbonyl in Chinese: 羰基
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