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.

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:

See also

• acetyl
• ketene
• indicator
• chemical synthesis

References

• NIH Thesaurus