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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. Thus: acetic acid (CH 3 COOH) → acetyl chloride (CH 3 COCl) benzoic acid (C 6 H 5 COOH) → benzoyl chloride (C 6 H 5 COCl) butyric acid (C 3 H 7 COOH) → butyryl chloride ...
Names of acyl groups of ribonucleoside monophosphates such as AMP (5′-adenylic acid), GMP (5′-guanylic acid), CMP (5′-cytidylic acid), and UMP (5′-uridylic acid) are adenylyl, guanylyl, cytidylyl, and uridylyl respectively. In phospholipids, the acyl group of phosphatidic acid is called phosphatidyl-. Finally, many saccharides are acylated.
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Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called adipoyl chloride, has two acyl chloride functional groups; see the structure at right. It is the dichloride (i.e., double chloride) of the 6-carbon dicarboxylic acid adipic acid.
The Tsuji–Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides. The reaction name recognizes JirÅ Tsuji, whose team first reported the use of Wilkinson's catalyst (RhCl(PPh 3) 3) for these reactions: RC(O)X + RhCl(PPh 3) 3 → RX + RhCl(CO)(PPh 3) 2 + PPh 3
However, for certain reactive acyl chlorides the activity must be reduced further, by the addition of a poison. Originally this was thioquinanthrene although thiourea [ 2 ] has also been used. [ 3 ] [ 4 ] Deactivation is required because the system must reduce the acyl chloride but not the subsequent aldehyde.
There are other processes of preparing an amide such as from acid anhydrides and acyl chloride. [2] Carboxylic acids react with ammonium carbonate, to convert the carboxylic acids to ammonium salts. For example, acetic acid reacts with ammonium carbonate to produce ammonium acetate. [3]