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Related Concept Videos

Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.

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Related Experiment Video

Updated: Jun 1, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

1-(4-Bromo-phen-yl)ferrocene.

Vincent O Nyamori1, Muhammad D Bala

  • 1School of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa.

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

This study details the crystal structure of a novel iron compound, [Fe(C(5)H(5))(C(11)H(8)Br)]. The ferrocenyl moiety exhibits a unique tilted geometry, stabilized by intermolecular C-H⋯π interactions.

Area of Science:

  • Organometallic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Ferrocene derivatives are crucial in catalysis and materials science.
  • Understanding the structural nuances of substituted ferrocenes informs their reactivity.
  • Intermolecular interactions play a significant role in crystal packing and material properties.

Purpose of the Study:

  • To elucidate the crystal structure of the novel compound [Fe(C(5)H(5))(C(11)H(8)Br)].
  • To analyze the geometric parameters of the ferrocenyl moiety, including ring tilts and inter-planar angles.
  • To identify and characterize the intermolecular interactions stabilizing the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

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Last Updated: Jun 1, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

  • Analysis of bond distances, angles, and torsion angles provided detailed geometric information.
  • Non-covalent interaction analysis was performed to identify stabilizing forces within the crystal.

    • Main Results:

    • The iron atom is equidistant from the centroids of the cyclopentadienyl (Cp) rings (1.644(1) and 1.643(1) Å).
    • The ferrocenyl moiety displays a deviation from eclipsed geometry, with tilted Cp rings and a 13.0(4)° inter-planar angle between Cp and benzene rings.
    • Crystal structure is stabilized by C-H⋯π interactions between Cp hydrogen atoms and Cp rings of adjacent molecules.

    Conclusions:

    • The determined structure provides valuable insights into the stereochemistry of substituted ferrocenes.
    • The observed C-H⋯π interactions highlight their importance in the self-assembly of organometallic compounds.
    • This structural data can guide the design of new functional ferrocene-based materials.