Acyl
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An acyl group (IUPAC name: alkanoyl) is a functional group derived by the removal of one or more hydroxyl groups from an oxoacid.[1] In organic chemistry, the acyl group is usually derived from a carboxylic acid. It therefore has the formula RC(=O)–, where R represents an alkyl group; there is a double bond between the carbon and oxygen atoms, and a single bond between R and the carbon. Acyl groups can also be derived from other types of acids such as sulfonic acids, phosphonic acids.
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[edit] In Reactions
Acyl halides can be used in Friedel-Crafts acylation to introduce the acyl moiety in an aromatic compound.
In biochemistry, acyl CoAs are derivates of fatty acid metabolism, with acetyl CoA as an example. They are actually thiol esters.
[edit] Examples
The names of acyl groups are typically derived from the corresponding acid by substituting the acid ending -ic with the ending -yl as shown in the table below. Note that methyl, ethyl, propyl, butyl, etc. that end in -yl are not acyl but alkyl groups derived from alkanes.
| Acyl group name (R-CO-) |
Corresponding carboxylic acid name (R-CO-OH) |
||
|---|---|---|---|
| common | systematic | common | systematic |
| formyl | methanoyl | formic acid | methanoic acid |
| acetyl | ethanoyl | acetic acid | ethanoic acid |
| propionyl | propanoyl | propionic acid | propanoic acid |
| benzoyl | benzoic acid | ||
| acryl | propenoyl | acrylic acid | propenoic acid |
[edit] Acyl species
In acyloxy groups the acyl group is bonded to oxygen: R-C(=O)-O-R' where R-C(=O) is the acyl group.
Acylium ions are cations of the type R-C+=O and play an important role as intermediates in organic reactions [1] for example the Hayashi rearrangement.
