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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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.
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.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...

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Related Experiment Video

Updated: Jun 1, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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N-(3-Nitro-benzyl-idene)aniline.

Muhammad Zaheer, Zareen Akhter, Michael Bolte

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

    This study details the crystal structure of a Schiff base derivative, C(13)H(10)N(2)O(2). The research reveals specific molecular geometry, including dihedral angles and trans configuration of the imine double bond, stabilized by intermolecular interactions.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Schiff bases are versatile organic compounds with diverse applications.
    • Understanding molecular structure is crucial for predicting material properties.
    • Intermolecular interactions play a key role in crystal packing and stability.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the Schiff base derivative C(13)H(10)N(2)O(2).
    • To analyze the molecular geometry, including dihedral and torsion angles.
    • To identify the intermolecular forces stabilizing the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • The molecular structure was determined and refined.

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  • Intermolecular interactions, such as C-H⋯O contacts and π-π stacking, were analyzed.

    • Main Results:

    • The dihedral angle between the aromatic rings was determined to be 31.58(3)°.
    • The C=N double bond was found to be coplanar with the nitro-phenyl ring.
    • The imine double bond adopts a trans configuration (torsion angle 175.97(13)°).
    • Crystal structure stabilization is attributed to C-H⋯O contacts and π-π interactions (3.807-3.808 Å).

    Conclusions:

    • The study provides a precise structural characterization of the Schiff base derivative.
    • The observed molecular geometry and intermolecular interactions offer insights into its solid-state behavior.
    • This structural data can inform the design of related compounds for specific applications.