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Related Concept Videos

Acidity of Carboxylic Acids01:21

Acidity of Carboxylic Acids

8.7K
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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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
8.8K
Acidity and Basicity of Carboxylic Acid Derivatives01:25

Acidity and Basicity of Carboxylic Acid Derivatives

4.2K
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...
4.2K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.5K
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...
3.5K
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

6.0K
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.
6.0K
Substituent Effects on Acidity of Carboxylic Acids01:31

Substituent Effects on Acidity of Carboxylic Acids

7.8K
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.
7.8K

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Updated: Jan 26, 2026

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Atmospheric Initial Nucleation Containing Carboxylic Acids.

Xia Sheng1, Benjin Wang1, Xue Song1

  • 1College of Chemistry, Chemical and Environmental Engineering , Henan University of Technology , Lianhua Street 100 , 450001 Zhengzhou , China.

The Journal of Physical Chemistry. A
|April 13, 2019
PubMed
Summary

This study reveals that clusters of organic acids like glyoxylic acid and oxalic acid with methyl hydrogen sulfate or methanesulfonic acid can form stable structures. These findings suggest their potential role in atmospheric new particle formation.

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Area of Science:

  • Atmospheric Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • Atmospheric new particle formation is crucial for climate but poorly understood.
  • The role of organic acid clusters in this process requires deeper investigation.

Purpose of the Study:

  • To investigate the properties of clusters formed by three organic acids (glyoxylic acid, oxalic acid, pyruvic acid) and three common nucleation precursors (methyl hydrogen sulfate, methanesulfonic acid, hydroxymethanesulfonic acid).
  • To determine the stability and characteristics of these clusters using advanced computational methods.

Main Methods:

  • Density Functional Theory (DFT) and ab initio coupled-cluster singles and doubles with perturbative triples (CCSD(T)) theory were employed.
  • Analysis of intermolecular hydrogen bonds (SO-H···O and CO-H···O) and their impact on cluster structure and stability.
  • Atoms in Molecules (AIM) topological analysis to characterize intermolecular interactions.

Main Results:

  • Six- to nine-membered cyclic structures stabilized by hydrogen bonds were identified.
  • Nine- and eight-membered cyclic complexes containing glyoxylic acid/oxalic acid/pyruvic acid with methyl hydrogen sulfate/methanesulfonic acid/hydroxymethanesulfonic acid showed higher thermodynamic stability.
  • Significant red shifts in OH-stretching frequencies and charge density analysis confirmed strong intermolecular interactions.
  • Methyl hydrogen sulfate- and methanesulfonic acid-containing complexes showed potential for new particle formation based on thermodynamic data, dipole moments, and mixing ratios.
  • Cluster concentrations increase significantly at higher altitudes (12 km).

Conclusions:

  • The study elucidates the structural and energetic properties of organic acid-sulfate clusters.
  • Methyl hydrogen sulfate- and methanesulfonic acid-containing clusters are identified as potential contributors to atmospheric new particle formation.
  • Small cluster calculations are valuable tools for simulating atmospheric new particle formation processes.