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Updated: Feb 15, 2026

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

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カーボキシル酸のバイオミメティック・デシメトリゼーション

Matthew T Knowe1, Michael W Danneman1, Sarah Sun1

  • 1Department of Chemistry & Vanderbilt Institute of Chemical Biology, Vanderbilt University , Nashville, Tennessee 37235-1822, United States.

Journal of the American Chemical Society
|February 6, 2018
PubMed
まとめ

チラル・ブロンステッド塩基触媒は,炭酸のエナチオ選択的脱対化を可能にし,高いステレオ制御を持つバイサイクルラクトンを生成する. この方法は,さらなる合成のために価値のある全炭素四分型ステレオセンターを作成します.

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Acidity of Carboxylic Acids01:21

Acidity of Carboxylic Acids

Carboxylic acids are the strongest organic acids. However, their acidic strength is much less than mineral acids like HCl. Carboxylic acids ionize in water and readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion.
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Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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Acidity and Basicity of Carboxylic Acid Derivatives

Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In comparison, the acid derivatives lack acidic hydrogens directly attached to a functional group. In these compounds, the acidic nature arises from their ability to lose α hydrogens, making them weakly acidic.
The relative acidic strength of the derivatives can be explained based on the extent of resonance stabilization of the conjugate base. The...
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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the stability of the carboxylate anion—the conjugate base formed by dissociating the corresponding carboxylic acid.
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Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
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