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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.
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...
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
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.

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Related Experiment Video

Updated: May 27, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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4-Nitro-N-(3-nitro-phen-yl)benzamide.

Dean H Johnston1, Colin R Taylor

  • 1Department of Chemistry, Otterbein University, Westerville, OH 43081, USA.

Acta Crystallographica. Section E, Structure Reports Online
|November 9, 2011
PubMed
Summary

This study details the crystal structure of a novel compound derived from 3-nitro-aniline and 4-nitro-benzoyl chloride. The molecule exhibits a non-planar structure with specific dihedral angles and forms layered structures through intermolecular interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • 3-nitro-aniline derivatives are important in organic synthesis.
  • Understanding molecular packing and intermolecular forces is crucial for material properties.

Purpose of the Study:

  • To characterize the crystal structure of a novel compound synthesized from 3-nitro-aniline and 4-nitro-benzoyl chloride.
  • To investigate the molecular conformation and intermolecular interactions in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided conformational details.
  • Identification of intermolecular interactions, such as C-H⋯O bonds, was performed.

Main Results:

  • The compound crystallizes in a chiral space group.
  • The molecule is non-planar with a significant dihedral angle between the benzene rings (26.1°).
  • Nitro groups exhibit slight twists (10.7° and 13.5°) out of their respective benzene ring planes.
  • Intermolecular C-H⋯O interactions lead to the formation of chains and layers in the crystal lattice.

Conclusions:

  • The synthesized compound possesses a unique non-planar molecular geometry.
  • Crystal packing is governed by specific intermolecular C-H⋯O interactions, forming extended chain and layered architectures.
  • The study provides insights into the solid-state behavior of nitro-substituted aromatic compounds.