Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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...

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

Determining the pH of Salt Solutions

Determining the pH of Salt Solutions

The pH of a salt solution is determined by its component anions and cations. Salts that contain pH-neutral anions and the hydronium ion-producing cations form a solution with a pH less than 7. For example, in ammonium nitrate (NH4NO3) solution, NO3− ions do not react with water whereas NH4+ ions produce the hydronium ions resulting in the acidic solution. In contrast, salts that contain pH-neutral cations and the hydroxide ion-producing anions form a solution with a pH greater than 7. For...

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.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

4,4'-Bi-pyridine-1,1'-diium tetra-chloridodi-fluorido-stannate(IV) monohydrate.

IUCrData·2025

Same author

Crystal structure and Hirshfeld surface analysis of tri-chlorido-(1,10-phenanthroline-κ<sup>2</sup> <i>N</i>,<i>N</i>')phenyltin(IV).

Acta crystallographica. Section E, Crystallographic communications·2024

Same author

Bis(2-carb-oxy-quinolinium) hexa-chlorido-stan-nate(IV) dihydrate.

IUCrData·2024

Same author

Synthesis and crystal structures of two 1H-benzo[d]imidazole derivatives: DFT and anticorrosion studies, and Hirshfeld surface analysis.

Acta crystallographica. Section C, Structural chemistry·2023

Same author

Crystal structure and Hirshfeld surface analysis of 1-[(<i>E</i>)-2-(3-nitro-phen-yl)diazen-1-yl]naphthalen-2-ol.

Acta crystallographica. Section E, Crystallographic communications·2023

Same author

Bis(2-amino-3,5-di-chloro-pyridinium) hexa-chlorido-stannate(IV) dihydrate.

IUCrData·2022

Search research articles

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-(Carboxy-meth-yl)anilinium chloride.

Habiba Kechout, Ratiba Belhouas, Sofiane Bouacida

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals the crystal structure of 4-(carboxymethyl)anilinium chloride, detailing how hydrophobic and hydrophilic layers stack. Hydrogen bonds between anions and cations stabilize this unique crystal arrangement.

Area of Science:

Crystallography
Materials Science
Chemical Physics

Background:

Understanding the packing of organic salts is crucial for predicting material properties.
The interplay of hydrogen bonding and molecular arrangement dictates crystal lattice stability.

Purpose of the Study:

To elucidate the crystal structure of 4-(carboxymethyl)anilinium chloride.
To identify and characterize the intermolecular interactions responsible for crystal stabilization.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
Analysis of hydrogen bonding networks (O-H⋯Cl, N-H⋯Cl, N-H⋯O, C-H⋯O, C-H⋯Cl) was performed.

Main Results:

The crystal structure exhibits alternating hydrophobic and hydrophilic layers stacked along the c axis.

More Related Videos

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

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

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

Published on: August 19, 2013

Related Experiment Videos

Last 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

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

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

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

Published on: August 19, 2013

Chloride anions are situated between 4-(carboxymethyl)anilinium layers, forming extensive hydrogen bonds.

Hydrogen bonds involving ammonium and carboxyl groups, along with weaker C-H⋯O and C-H⋯Cl interactions, contribute to structural integrity.

Conclusions:

The crystal structure of 4-(carboxymethyl)anilinium chloride is stabilized by a combination of strong and weak intermolecular hydrogen bonds.
The layered arrangement of hydrophobic and hydrophilic zones influences the overall crystal packing and stability.