Are you an EPFL student looking for a semester project?
Work with us on data science and visualisation projects, and deploy your project as an app on top of Graph Search.
Concept
Carbonyl group
Summary
In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double-bonded 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 acids), 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, where carbon and oxygen share a double bond.
α,β-Unsaturated carbonyl compound
In organic chemistry, a carbonyl group characterizes the following types of compounds:
Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. 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.
For organic compounds, the length of the C-O bond does not vary widely from 120 picometers. Inorganic carbonyls have shorter C-O distances: CO, 113; CO2, 116; and COCl2, 116 pm.
The carbonyl carbon is typically electrophilic. A qualitative order of electrophilicity is RCHO (aldehydes) > R2CO (ketones) > RCO2R' (esters) > RCONH2 (amides). A variety of nucleophiles attack, breaking the carbon-oxygen double 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. ΔHσ values are much higher 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.
Official source
About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.
Ontological neighbourhood
Related courses (10)
CH-432: Structure and reactivity
To develop a detailed knowledge of the key steps of advanced modern organic synthesis going beyond classical chemistry of olefins and carbonyls.
CH-442: Photochemistry I
This course presents the theoretical bases of electronic spectroscopy and molecular photophysics. The principles of the reactivity of excited states of molecules and solids under irradiation are detai
CH-233: Organic functions and reactions I
Le cours se focalisera sur les composés carbonyles: leur structures, réactivités, et leurs transformations; la réactivité des énols/énolates et leurs réactions fondamentales. L'importance de la compré
Related lectures (37)
Metal Carbonyls: Bonding
Covers the bonding in metal carbonyls and the Mond process for nickel purification.
Redox Reactions of Aldehydes
Explores redox reactions of aldehydes, such as Tishchenko and Wolff-Kishner-Huang Reductions, and stereocontrolled Evans-Tishchenko Reaction.
Redox Reactions of Aldehydes
Explores redox reactions of aldehydes, including Evans-Tishchenko, Cannizzaro, and Benzoin reactions, reduction of imines, and Wittig reaction variants.
Related publications (109)
Organic Dye Photocatalyzed Synthesis of Functionalized Lactones and Lactams via a Cyclization-Alkynylation Cascade
An organic dye photocatalyzed lactonization-alkynylation of easily accessible homoallylic cesium oxalates using ethynylbenziodoxolone (EBX) reagents has been developed. The reaction gave access to valuable functionalized lactones and lactams in up to 88% y ...
Amer Chemical Soc2024Role of Carbonyl Compounds for N-Nitrosamine Formation during Nitrosation: Kinetics and Mechanisms
Urs von Gunten, Florian Frédéric Vincent Breider, Yishuai Pan
N-Nitrosamines are potential human carcinogens frequently detected in natural and engineered aquatic systems. This study sheds light on the role of carbonyl compounds in the formation of N-nitrosamines by nitrosation of five secondary amines via different ...
2024Aptamer-Functionalized Interface Nanopores Enable Amino Acid-Specific Peptide Detection
Nako Nakatsuka, Xinyu Zhang, Haiying Hu
Single-molecule proteomics based on nanopore technology has made significant advances in recent years. However, to achieve nanopore sensing with single amino acid resolution, several bottlenecks must be tackled: controlling nanopore sizes with nanoscale pr ...
2024Related people (27)
Related units (7)
Related concepts (37)
Acyl chloride
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example of an acyl chloride is acetyl chloride, . Acyl chlorides are the most important subset of acyl halides. Where the acyl chloride moiety takes priority, acyl chlorides are named by taking the name of the parent carboxylic acid, and substituting -yl chloride for -ic acid.
Phosgene
Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.
Isocyanate
In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers. Isocyanates should not be confused with cyanate esters and isocyanides, very different families of compounds. The cyanate (cyanate ester) functional group () is arranged differently from the isocyanate group ().