Carbonyl group

 ( Functional Groups ) 

In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes, ketones and carboxylic acid), as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.

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).

The remainder of this article concerns itself with the organic chemistry definition of carbonyl, such that carbon and oxygen share a double bond.

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Carbonyl compounds In organic chemistry, a carbonyl group characterizes the following types of compounds:

Other organic carbonyls are urea and the , the derivatives of , and phosgene, , , , , Hydroxamic acid, and . Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide.

A special group of carbonyl compounds are dicarbonyl compounds, which can exhibit special properties.

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Structure and reactivity For organic compounds, the length of the C–O bond does not vary widely from 120 . Inorganic carbonyls have shorter C–O distances: carbon monoxide, 113; carbon dioxide, 116; and phosgene, 116 pm.

G. Berthier, J. Serre (1966). 9780470771051, John Wiley & Sons. ISBN 9780470771051

The carbonyl carbon is typically electrophile. A qualitative order of electrophilicity is RCHO (aldehydes) > R₂CO (ketones) > RCO₂R' (esters) > RCONH₂ (amides). A variety of nucleophiles attack, breaking the carbon-oxygen Pi bond.

Interactions between carbonyl groups and other substituents were found in a study of collagen. Substituents can affect carbonyl groups by addition or subtraction of electron density by means of a sigma bond. Δ Hσ values are much greater when the substituents on the carbonyl group are more electronegative than carbon.

The polarity of C=O bond also enhances the acidity of any adjacent C-H bonds. Due to the positive charge on carbon and the negative charge on oxygen, carbonyl groups are subject to additions and/or nucleophilic attacks. A variety of nucleophiles attack, breaking the carbon-oxygen Pi bond, and leading to addition-elimination reactions. Nucleophilic reactivity is often proportional to the basicity of the nucleophile and as nucleophilicity increases, the stability within a carbonyl compound decreases. The pK_a values of acetaldehyde and acetone are 16.7 and 19 respectively,Ouellette, R.J. and Rawn, J.D. "Organic Chemistry" 1st Ed. Prentice-Hall, Inc., 1996: New Jersey.

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Spectroscopy

• Infrared spectroscopy: the C=O double bond absorbs infrared light at between approximately 1600–1900 cm⁻¹(5263 nm to 6250 nm). 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.Mayo D.W., Miller F.A and Hannah R.W “Course Notes On The Interpretation of Infrared and Raman Spectra” 1st Ed. John Wiley & Sons Inc, 2004: New Jersey. . In addition, the ultraviolet-visible spectra of propanone in water gives an absorption of carbonyl at 257 nm.
• 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.

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See also

• Carbon–oxygen bond
• Organic chemistry
• Functional group
• Bridging carbonyl
• Electrophilic addition

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Further reading

• L.G. Wade, Jr. Organic Chemistry, 5th ed. Prentice Hall, 2002.
• The Frostburg State University Chemistry Department. Organic Chemistry Help (2000).
• Advanced Chemistry Development, Inc. IUPAC Nomenclature of Organic Chemistry (1997).
• William Reusch. tara VirtualText of Organic Chemistry (2004).
• Purdue Chemistry Department [4] (retrieved Sep 2006). Includes water solubility data.
• William Reusch. (2004) Aldehydes and Ketones Retrieved 23 May 2005.
• ILPI. (2005) The MSDS Hyperglossary- Anhydride.

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