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Preparation of Acid Anhydrides

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...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

Ionic Compounds: Formulas and Nomenclature

Ionic Compounds: Formulas and Nomenclature

An element composed of atoms that readily lose electrons (a metal) can react with an element composed of atoms that readily gain electrons (a nonmetal) to produce ions through complete electron transfer. The compound formed by this transfer is stabilized by the electrostatic attractions (ionic bonds) between the oppositely charged ions.

Precipitation of Ions

Precipitation of Ions

Predicting Precipitation
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:

Alkyl Halides

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

Reactions of Acid Anhydrides

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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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Hy-droxy-anilinium perchlorate dihydrate.

¹Ordered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This study details the crystal structure of a protonated amine perchlorate hydrate. It reveals extensive hydrogen bonding networks involving cations, anions, and water molecules, alongside weak C-H···π interactions.

Area of Science:

Crystallography
Supramolecular Chemistry
Chemical Physics

Background:

Understanding the intricate intermolecular interactions within crystalline solids is crucial for predicting and controlling material properties.
Protonated amine salts with perchlorate anions are of interest due to their potential applications and unique structural motifs.

Purpose of the Study:

To elucidate the detailed crystal structure of the title compound, C(6)H(8)NO(+)·ClO(4) (-)·2H(2)O.
To characterize the hydrogen bonding network and other intermolecular forces governing the crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional atomic arrangement of the compound.
Analysis of the resulting crystal structure data allowed for the identification of hydrogen bonds and C-H···π interactions.

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Main Results:

The crystal structure is characterized by extensive intermolecular hydrogen bonds, including N-H···O and O-H···O interactions.
Water molecules act as crucial linkers between the protonated amine cations and perchlorate anions.
Weak intermolecular C-H···π interactions were also observed, contributing to the overall crystal stability.

Conclusions:

The crystal structure of C(6)H(8)NO(+)·ClO(4) (-)·2H(2)O is stabilized by a robust network of hydrogen bonds mediated by water molecules.
The interplay of hydrogen bonding and weaker interactions dictates the supramolecular architecture of this protonated amine perchlorate hydrate.