Dmf In Acid Chloride Formation
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The acyl chloride or the acyl anhydride is thermodynamically unstable and tends to transform to the ketone by the addition of base or catalyst. The acyl anhydride has an advantage over the acyl chloride in that it is a single optical isomer which simplifies the separation of the products. The reaction of the acyl anhydride with amine proceeds via the addition of the amine to the carboxylic acid group. The acyl chloride reacts with amine to give an amide, which in turn can be converted to the corresponding amine salt or amide.
The acyl halides or the acyl anhydrides are usually prepared starting from carboxylic acids, carboxylic acids . The carboxylic acid is converted to the carboxylic acid halide or the carboxylic acid anhydride via various reaction conditions. The carboxylic acid halide or the carboxylic acid anhydride is then used for the addition of amine.
Acyl chlorides are unstable compounds which usually are commercially available only as a mixture of isomers. The most thermodynamically stable forms are the E-isomers, and the least stable are the Z-isomers. The E-isomer is converted to the corresponding amide by the action of amine at room temperature. The E-isomer is less reactive, but more stable. Z-isomer is the most reactive, but thermodynamically unstable and requires higher reaction temperatures to achieve the same conversion to the corresponding amide. ACOCl is converted to the corresponding ester by the action of an alkanol at room temperature, and the ester is thermodynamically stable.
Acyl chloride is able to react with amine when the following conditions are met:
Acyl chloride is strong enough to compete with the nucleophile and overcome the electronic differences between the R group and the amine nitrogen. The R group must be electron rich in order to make the nucleophile attack possible.
The amine must be acidic enough to protonate the acyl chloride. It must be a strong base, with a pKa less than the acyl chloride.
The electronic difference between the amine and the acyl chloride is enough to allow the formation of a C–N bond. The acyl chloride must have a weak electron withdrawing group or electron donating group close to the nitrogen in order to facilitate the formation of a C–N bond.
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