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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...
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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

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Updated: May 31, 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-(4-nitro-benzo-yl)benzamide.

Sohail Saeed, Naghmana Rashid, Seik Weng Ng

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary

    This study details the crystal structure of a novel compound, C(14)H(9)N(3)O(6), revealing a curved molecular geometry. Hydrogen bonding influences the crystal packing, forming twisted chains.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Crystal structure analysis provides precise details about molecular conformation and intermolecular interactions.

    Purpose of the Study:

    • To elucidate the detailed crystal structure and molecular geometry of the title compound, C(14)H(9)N(3)O(6).
    • To investigate the influence of intermolecular forces, such as hydrogen bonding, on the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
    • Analysis of torsion angles, dihedral angles, and root-mean-square deviations was performed to describe the molecular conformation.

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  • Identification and analysis of hydrogen bonding networks within the crystal structure.

    • Main Results:

    • The central acetyl-acetamide moiety exhibits a buckled conformation with a C-N-C-O torsion angle of 14.3°.
    • The benzene rings are positioned on the same side of the central plane, contributing to a curved molecular shape with a dihedral angle of 17.8° between them.
    • Intramolecular N-H⋯O hydrogen bonds were observed, leading to the formation of twisted chains along the b-axis in the crystal lattice.
    • Positional disorder of oxygen atoms in the nitro groups was modeled with a 50:50 occupancy ratio.

    Conclusions:

    • The crystal structure of C(14)H(9)N(3)O(6) reveals a significantly curved molecular architecture.
    • Intermolecular hydrogen bonding plays a key role in organizing the molecules into specific chain structures within the crystal.
    • The findings provide valuable insights into the solid-state behavior and structural characteristics of this class of compounds.