Acylation


Acylation

In chemistry, acylation (rarely, but more formally: alkanoylation) is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent. These are used to form aryl ketones.

Because they form a strong electrophile when treated with some metal catalysts, acyl halides are commonly used as acylating agents. For example, Friedel-Crafts acylation uses acetyl chloride (ethanoyl chloride), CH3COCl, as the agent and aluminum chloride (AlCl3) as a catalyst to add an ethanoyl(acetyl) group to benzene:



The mechanism of this reaction is electrophilic substitution.

Acyl halides and anhydrides of carboxylic acids are also commonly used acylating agents to acylate amines to form amides or acylate alcohols to form esters. The amines and alcohols are nucleophiles; the mechanism is nucleophilic addition-elimination. Succinic acid is also commonly used in a specific type of acylation called "succination". "Oversuccination" occurs when more than one succinate adds to a single compound. An industrial example of acylation in the synthesis of aspirin, in which salicylic acid is acylated by acetic anhydride.

Mechanism of Friedel Crafts:

ee also

*acetyl
*ketene
*indicator
*chemical synthesis

References

* [http://crisp.cit.nih.gov/Thesaurus/00000094.htm NIH Thesaurus]


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  • acylation — ● acylation nom féminin Substitution, dans une molécule, d un atome d hydrogène par un radical acyle R―CO―. (C est une des réactions les plus importantes de la synthèse organique.) acylation [asilɑsjɔ̃] n. f. ÉTYM. 1904, in Rev. gén. des sc.,… …   Encyclopédie Universelle

  • Acylation — En chimie organique, une acylation est une réaction au cours de laquelle un groupement acyle est ajouté à une molécule, ce groupement étant transféré depuis un agent acylant. Les halogénures d acyle sont très utilisés comme agents acylants. En… …   Wikipédia en Français

  • acylation — acilinimas statusas T sritis chemija apibrėžtis RCO– grupės įjungimas į molekulę. atitikmenys: angl. acylation rus. ацилирование …   Chemijos terminų aiškinamasis žodynas

  • acylation — noun see acylate …   New Collegiate Dictionary

  • acylation — Introduction of an acyl (RCO ) group into a molecule: for example the formation of an ester between glycerol and fatty acid to form mono , di , or tri acylglycerol, or the formation of an aminoacyl tRNA during protein synthesis. Acyl enzyme… …   Dictionary of molecular biology

  • acylation — noun The process of adding an acyl group to a compound …   Wiktionary

  • acylation — Introduction of an acyl radical into an organic compound or formation of such a radical within an organic compound. * * * ac·yl·a·tion (a″sə laґshən) the introduction of an acyl radical into the molecule of a chemical compound …   Medical dictionary

  • acylation — ac·yl·a·tion …   English syllables

  • acylation — noun the process of introducing an acyl group into a compound • Hypernyms: ↑chemical process, ↑chemical change, ↑chemical action • Hyponyms: ↑acetylation * * * ˌasəˈlāshən noun ( s …   Useful english dictionary

  • Acylation de Friedel-Crafts — Réaction de Friedel Crafts Les réactions de Friedel Crafts sont des réactions chimiques de type substitution électrophile aromatique au cours desquelles un cycle benzènique est alkylé (substitution d un atome d hydrogène par un groupement alkyle) …   Wikipédia en Français