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. Therefore, it has the formula RCO-, where R represents an alkyl group that is attached to the CO group with a single bond. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids, phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.

Contents

Acyl compounds

Well-known acyl compounds are the acyl chlorides, such as acetyl chloride (CH3COCl) and benzoyl chloride (C6H5COCl). These compounds, which are treated as sources of acylium cations, are good reagents for attaching acyl groups to various substrates. Amides (RC(O)NR2) and esters (RC(O)OR’) are classes of acyl compounds, as are ketones (RC(O)R) and aldehydes (RC(O)H).

Acylium cations, anions, and radicals

Acylium ions are cations of the type R-C+=O.[1] The oxygen and carbon are linked by a triple bond. Such species are common reactive intermediates, for example, in the Friedel-Crafts acylation. Furthermore, acylium cations are characteristic fragments observed in EI-mass spectra of ketones. Acylium intermediates occur in many organic reactions such as the Hayashi rearrangement. Salts containing acylium ions are also generated when acyl halides are treated with pyridines and with tertiary amines:

Acyl anions are unknown and organolithium compounds with Li-C(O)R linkages are not well studied.

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