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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.
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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for 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
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

4-Anilino-3-nitro-benzonitrile.

Yong Wang, Kaiqing Fan, Chenghong Li

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of a benzonitrile derivative, revealing twisted aromatic rings and stabilizing intermolecular interactions. The findings contribute to understanding molecular packing in organic compounds.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
    • Benzonitrile derivatives are important building blocks in various chemical applications.
    • Intermolecular forces play a significant role in stabilizing crystal structures.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(13)H(9)N(3)O(2).
    • To analyze the molecular geometry, including aromatic ring orientation and substituent planarity.
    • To investigate the types and roles of intermolecular interactions in stabilizing the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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  • Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
  • Identification and quantification of intra- and intermolecular interactions, including hydrogen bonds and pi-pi stacking.

    • Main Results:

    • The crystal structure revealed twisted aromatic rings with a dihedral angle of 49.41(9)°.
    • Nitro and nitrile groups were found to be nearly coplanar with the benzonitrile ring.
    • An intramolecular N-H⋯O hydrogen bond formed an S(6) ring, and weak intermolecular C-H⋯O hydrogen bonds created chains parallel to the c axis.
    • Slipped pi-pi interactions between phenyl rings further stabilized the crystal structure.

    Conclusions:

    • The title compound C(13)H(9)N(3)O(2) exhibits a unique molecular arrangement stabilized by a combination of intramolecular hydrogen bonding and intermolecular forces.
    • The observed twisted aromatic rings and pi-pi interactions are key features influencing the compound's solid-state structure.
    • This structural characterization provides valuable data for further research into the properties and applications of benzonitrile derivatives.