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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

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...
Amines to Amides: Acylation of Amines01:19

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...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Diazonium Group Substitution: –OH and –H01:19

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.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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Related Experiment Video

Updated: Jun 1, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Phenyl-methanaminium chloro-acetate.

Durre Shahwar, M Nawaz Tahir, Naeem Ahmad

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of a phenyl-methanaminium chloracetate salt. Molecular interactions, including hydrogen bonds and pi-interactions, form a crystal network.

    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Understanding the solid-state structure of organic salts is crucial for predicting their physical and chemical properties.
    • Phenyl-methanaminium (PM) derivatives are important in various chemical applications.
    • Chloracetate anions are common counterions with distinct electronic properties.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of phenyl-methanaminium chloracetate.
    • To analyze the spatial arrangement and bonding characteristics of the cation and anion.
    • To investigate the role of hydrogen bonding and other weak interactions in stabilizing the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.

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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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    04:38

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

    Published on: July 28, 2022

  • Crystallographic analysis was performed to measure bond lengths, angles, and dihedral angles.
  • Intermolecular interactions, such as hydrogen bonds and C-H···π interactions, were identified and analyzed.

    • Main Results:

    • The crystal structure consists of planar phenyl-methanaminium cations and planar chloracetate anions.
    • A dihedral angle of 31.07° was observed between the cation and anion planes.
    • Intermolecular N-H···O hydrogen bonds form a robust network, linking molecules into a stable crystal structure.
    • A weak C-H···π interaction was also identified, contributing to the overall crystal packing.

    Conclusions:

    • The crystal structure of phenyl-methanaminium chloracetate is characterized by specific orientations between the cation and anion.
    • Hydrogen bonding plays a significant role in the self-assembly and stabilization of the crystal lattice.
    • The identified weak interactions provide insights into the supramolecular chemistry of this organic salt.