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Preparation and physical properties of chitosan benzoic acid derivatives using a phosphoryl mixed anhydride system

Duckhee Lee1, Zhe Shan Quan, Chichong Lu

  • 1The Division of Bio-Nanochemistry, The College of Natural Sciences, The Wonkwang University, Iksan City, Chonbuk 570-749, Korea.

Molecules (Basel, Switzerland)
|February 24, 2012
PubMed

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Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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Reactions of Acid Anhydrides

The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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Structures of Carboxylic Acid Derivatives

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Acid Halides to Carboxylic Acids: Hydrolysis

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