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Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

3.9K
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...
3.9K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.6K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.6K
Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

5.1K
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.
5.1K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.5K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
5.5K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.4K
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...
3.4K
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

5.8K
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.
5.8K

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Updated: Jan 2, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Carboxylic Sulfuric Anhydrides.

C J Smith1, Anna K Huff1, Rebecca M Ward1

  • 1Department of Chemistry , University of Minnesota , 207 Pleasant Street, SE , Minneapolis , Minnesota 55455 , United States.

The Journal of Physical Chemistry. A
|December 3, 2019
PubMed
Summary
This summary is machine-generated.

New research characterizes carboxylic sulfuric anhydrides, revealing near-zero formation barriers and potential atmospheric roles. These compounds, formed from carboxylic acids and sulfur trioxide, could be significant atmospheric species.

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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
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Area of Science:

  • Physical Chemistry
  • Atmospheric Chemistry
  • Spectroscopy

Background:

  • Carboxylic acids react with sulfur trioxide (SO3) to form carboxylic sulfuric anhydrides (RCOOSO2OH).
  • This class of compounds is not widely characterized in chemical literature.
  • Understanding their formation and properties is crucial for sulfur oxide and oxyacid chemistry.

Purpose of the Study:

  • To present new supersonic jet microwave spectra for propiolic acid anhydride.
  • To review recent work on various carboxylic sulfuric anhydrides.
  • To compare structural and energetic features of anhydrides derived from different carboxylic acids.

Main Methods:

  • Supersonic jet microwave spectroscopy was used to study propiolic acid anhydride.
  • Computational chemistry (CCSD(T)/CBS, M06-2X) was employed to determine structures and energy barriers.
  • Statistical thermodynamics was applied to estimate equilibrium constants for anhydride formation.

Main Results:

  • The barrier to anhydride formation from propiolic acid was found to be effectively zero after zero-point energy corrections.
  • Equilibrium constants for formation reactions vary significantly with the carboxylic acid used, ranging up to 10^11 atm^-1.
  • Estimated atmospheric concentrations of carboxylic sulfuric anhydrides could reach 10^7 molecules/cm^3 and may exceed those of sulfuric acid precursors.

Conclusions:

  • Carboxylic sulfuric anhydrides form readily, with near-zero energy barriers.
  • These anhydrides have the potential to be significant species in Earth's atmosphere.
  • Further kinetic modeling is needed to fully assess their atmospheric role.