Acyl Chloride
Acyl Chloride - 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.
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.
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.
07:32
Dynamic Electrochemical Measurement of Chloride Ions
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Cited by 5 •
2016
Dynamic measurement of chloride ions is presented. Transition time of an Ag/AgCl electrode, during a chronopotentiometric technique, can give the concentration of chloride ions in electrolyte. This method does not require a stable conventional reference electrode.
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 reaction begins when a nucleophile attacks the strongly electrophilic carbonyl carbon. This forms a transient acyl intermediate, after which chloride is displaced and the carbonyl group is restored. The substitution pathway explains why different nucleophiles can replace chlorine with distinct groups, while hydrogen chloride commonly appears as a byproduct of the transformation.
The carbonyl carbon is strongly electrophilic, so it readily attracts electron-rich nucleophiles. Their attack initiates replacement of chloride under relatively mild conditions rather than requiring severe reaction conditions. This high reactivity makes acyl chlorides useful when chemists need to introduce an acyl group efficiently into another molecule.
The nucleophile determines which new acyl compound forms. Water converts the reactive group into a carboxylic acid, alcohols produce esters, and amines produce amides. Thus, changing the reaction partner changes the functional group attached to the carbonyl, allowing chemists to prepare different classes of carbonyl-containing compounds from the same starting reagent.
Chemists select the nucleophile according to the desired product: water gives a carboxylic acid, an alcohol gives an ester, and an amine gives an amide. In each case, nucleophilic attack is followed by chloride replacement. This predictable relationship provides a direct route for converting one acyl reagent into several useful compound types.
A typical sequence involves bringing the acyl chloride into contact with the selected nucleophile, allowing nucleophilic attack at the carbonyl carbon, and forming the corresponding substituted acyl compound. Chloride is displaced during the process, and hydrogen chloride may form. The sequence is useful because it connects reagent choice directly to the targeted product.
Their high reactivity enables the formation of new carbonyl compounds under mild conditions, including esters and amides that can serve as structural units in larger molecules. Chemists can therefore use them to introduce precisely modified carbonyl groups during synthesis. This capability supports applications in pharmaceuticals, polymers, fragrances, and other areas of organic chemistry.