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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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.
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...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Related Experiment Video

Updated: May 20, 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

5-Nitro-1-benzofuran-2(3H)-one.

Xin-Yi Han, Ya-Bin Shi, Hong Shen

    Acta Crystallographica. Section E, Structure Reports Online
    |July 19, 2012
    PubMed
    Summary

    This study reveals the crystal structure of C(8)H(5)NO(4), detailing how planar molecules stack and form dimers through weak hydrogen bonds. These findings offer insights into molecular arrangement and intermolecular interactions.

    Area of Science:

    • Crystallography
    • Materials Science
    • Chemical Physics

    Background:

    • Understanding molecular packing is crucial for predicting material properties.
    • Crystal structure analysis provides fundamental insights into intermolecular forces.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(8)H(5)NO(4).
    • To investigate the packing arrangement and intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of molecular planarity and intermolecular distances was performed.

    Main Results:

    • The crystal structure features essentially planar molecules with the largest deviation from the least-squares plane being 0.030(2) Å.

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
    08:43

    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

    Published on: January 19, 2016

  • Molecules form stacks along the a-axis with intercentroid separations of 3.6594(12) Å and 3.8131(12) Å between overlapping benzene rings.
  • Weak C-H⋯O hydrogen bonds link molecules from neighboring stacks into inversion dimers.

    • Conclusions:

    • The crystal packing is dominated by π-π stacking interactions and hydrogen bonding.
    • The identified structural features provide a basis for understanding the compound's physical and chemical behavior.