Acid Halide

acid halide, neutral compound that reacts with water to produce an acid and a hydrogen halide. Acid halides are ordinarily derived from acids or their salts by replacement of hydroxyl groups by halogen atoms. The most important organic acid halides are the chlorides derived from carboxylic acids and from sulfonic acids. The carboxylic acid chlorides, called acyl halides, are generally more reactive than the sulfonic acid chlorides, called sulfonyl chlorides.

The acyl halides are highly reactive substances used primarily in organic syntheses to introduce the acyl group. They react with water, ammonia, and alcohols to give carboxylic acids, amides, and esters, respectively.

Most acyl halides are liquids insoluble in water. They have sharp odours and irritate the mucous membranes. Sulfonyl chlorides (RSO₂Cl) react with ammonia to form sulfonamides, including the sulfa drugs.

Common halides of inorganic acids include chlorosulfuric acid (ClSO₃H; formerly called chlorosulfonic acid) and sulfuryl chloride (SO₂Cl₂), corresponding to the replacement of one or both hydroxyl groups of sulfuric acid, H₂SO₄ or SO₂(OH)₂; thionyl chloride (SOCl₂), the chloride of sulfurous acid; phosphorus trichloride (PCl₃), the chloride of phosphorous acid; and phosphorus oxychloride (POCl₃, also called phosphoryl chloride), the chloride of phosphoric acid.