Oxoacid compound with an –OH group replaced by a halogen
Acyl Halide
In organic chemistry, an acyl halide (also known as an acid halide) is a chemical compound derived from an oxoacid[1] by replacing a hydroxyl group (−OH) with a halide group (−X, where X is a halogen).[2]
If the acid is a carboxylic acid (−C(=O)OH), the compound contains a −C(=O)X functional group, which consists of a carbonyl group (C=O) singly bonded to a halogen atom.[3] The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl group, CO is the carbonyl group, and X represents the halide, such as chloride. Acyl chlorides are the most commonly encountered acyl halides, but acetyl iodide is the one produced (transiently) on the largest scale. Billions of kilograms are generated annually in the production of acetic acid.[4]
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "acyl groups". doi:10.1351/goldbook.A00123
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "acyl halides". doi:10.1351/goldbook.A00124
^Saul Patai, ed. (1972). Acyl Halides. PATAI'S Chemistry of Functional Groups. doi:10.1002/9780470771273. ISBN 9780470771273.
^Hosea Cheung, Robin S. Tanke, G. Paul Torrence "Acetic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_045
acylium ions can be generated by removal of the halide from acylhalides: RC(O)Cl + SbCl5 → [RCO]+[SbCl6]− Acyl radicals are readily generated from aldehydes...
chloride (also called methoxybenzoyl chloride) is an acylhalide, specifically an aromatic acyl chloride, and may be formed from anisic acid by replacing...
halide to the end of the acyl group. For example, CH3COCl is ethanoyl chloride. An alternate suffix is "-carbonyl halide" as opposed to "-oyl halide"...
example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acylhalides. Where the acyl chloride moiety...
the formula ClCO2H. It is the single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative). Chloroformic acid is also...
amine, or enolate – displaces the leaving group of an acyl derivative – such as an acid halide, anhydride, or ester. The resulting product is a carbonyl-containing...
Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones...
procedure is the Arndt–Eistert synthesis, where an acid is converted into acylhalide, which is then reacted with diazomethane to give one additional methylene...
The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general...
Acid anhydrides are a source of reactive acyl groups, and their reactions and uses resemble those of acylhalides. In reactions with protic substrates, the...
R'COCl → R'COSR + NaCl Another common route entails the displacement of halides by the alkali metal salt of a thiocarboxylic acid. For example, thioacetate...
recalcitrant alkyl halide. Alternatively, salts of a coordinating metal, such as silver, may improve the reaction rate by easing halide elimination. Transesterification...
carbonyl-component may be part of either a carboxylic acid group or the more reactive acylhalide derivative. The amine group and the carboxylic acid group can be on the...
Prozac have trifluoromethyl groups. For information on inorganic halide chemistry, see halide. Halocarbons are typically classified in the same ways as the...
reduction to B 12s, followed by the addition of the corresponding alkyl halides, acylhalides, alkene or alkyne. Steric hindrance is the major limiting factor...
ester can also be produced with an acylhalide and an alcohol, in which case the condensate by-product is a hydrogen halide. Polyesters are a category of polymers...
ions to give coordination complexes. Amines are alkylated by alkyl halides. Acyl chlorides and acid anhydrides react with primary and secondary amines...
moieties themselves or to radical species, and also to form the names of halides and substituents in larger molecules. When the parent hydrocarbon is unsaturated...
of alkyl groups to molecules, often by alkylating agents such as alkyl halides. Alkylating antineoplastic agents are a class of compounds that are used...
Because they form a strong electrophile when treated with Lewis acids, acylhalides are commonly used as acylating agents. For example, Friedel–Crafts acylation...
in the presence of an acid catalyst or UV light. Halide displacement, using the suitable organic halide and sodium hydrogen sulfide has also been used....
base such as powdered potassium hydroxide or sodium hydride and benzyl halide (BnCl or BnBr) Monobenzylation of diols can be achieved using Ag2O in dimethylformamide...
nucleophiles, less electrophilic reagents are employed, such as ethyl halides. In unsymmetrical ethylated compounds, the methylene protons in the ethyl...
In inorganic chemistry, sulfonyl halide groups occur when a sulfonyl (>S(=O)2) functional group is singly bonded to a halogen atom. They have the general...
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