Acyl Halides
Acyl Halides - Related Videos
09:58
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Cited by 3 •
2015
The goal of this manuscript is to demonstrate a straightforward method for the preparation of ynones from acyl chloride and potassium alkynyltrifluoroborate salt starting materials. The one-pot reaction proceeds rapidly in the presence of boron trichloride without exclusion of air and moisture.
08:31
Detection of Protein S-Acylation using Acyl-Resin Assisted Capture
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Cited by 29 •
2020
Acyl-RAC (Acyl-Resin Assisted Capture) is a highly sensitive, reliable and easy to perform method to detect reversible lipid modification of cysteine residues (S-acylation) in a variety of biological samples.
12:06
Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
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Cited by 7 •
2017
Sialic acid is a typical monosaccharide-unit found in glycoconjugates. It is involved in a plethora of molecular and cellular interactions. Here we present a method to modify cell surface sialic acid expression using metabolic glycoengineering with N-acetylmannosamine derivatives.
02:45
Alkyl Halides
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2023
Structural Properties Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape. Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
01:19
Amines to Amides: Acylation of Amines
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2025
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond. Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
FAQs
The key mechanistic event is attack by a nucleophile at the strongly electrophilic carbonyl carbon. This interaction enables replacement of the attached halide, which functions as a good leaving group. The substitution changes the acyl compound into a new derivative, allowing the same reactive framework to produce different products depending on which nucleophile participates.
Acid chlorides are commonly selected because they readily react with several important nucleophiles, including water, alcohols, and amines. Their high reactivity makes them useful intermediates when a synthesis requires efficient conversion into another carboxylic acid derivative. This behavior supports laboratory-scale preparation as well as larger synthetic strategies involving pharmaceuticals, polymers, and materials.
The nucleophile determines which group replaces the halide and therefore controls the product class. Water produces a carboxylic acid, an alcohol produces an ester, and an amine produces an amide. This direct relationship lets chemists select the reacting partner according to the functional group needed in a target molecule or intermediate.
A basic workflow begins by selecting the acyl halide and a nucleophile that will provide the desired product type. The reactants are then brought together so nucleophilic acyl substitution can occur, followed by identification or use of the resulting carboxylic acid, ester, or amide. The approach offers a direct route for changing one reactive intermediate into another useful compound.
Researchers use these intermediates when they need a direct and efficient way to form carboxylic acid derivatives or construct carbon-heteroatom bonds. Their reactions with water, alcohols, and amines provide predictable routes to acids, esters, and amides. Consequently, they can support compound preparation in pharmaceutical research, polymer development, materials chemistry, and laboratory synthesis.
Acyl halide reactions can generate several important functional groups while supporting construction of carbon-carbon and carbon-heteroatom bonds. In particular, conversion with water, alcohols, or amines gives carboxylic acids, esters, or amides, respectively. These products are valuable as final compounds or intermediates, linking the reaction to broader organic synthesis in chemistry.