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Related Concept Videos

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...
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.
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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Related Experiment Video

Updated: Jun 1, 2026

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

Dibenzo[b,e]thiepin-11(6H)-one.

Jerry P Jasinski, Q N M Hakim Al-Arique, Ray J Butcher

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

    The crystal structure of a C14H10OS compound reveals a seven-membered thiepin ring. This ring adopts a distorted boat conformation, influencing the molecule's overall three-dimensional shape.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Thiepin derivatives are sulfur-containing heterocyclic compounds with diverse chemical properties.
    • Understanding the conformational preferences of thiepin rings is crucial for predicting molecular behavior and designing new compounds.

    Purpose of the Study:

    • To elucidate the three-dimensional structure of the title compound, C14H10OS.
    • To characterize the conformational aspects of the seven-membered thiepin ring within this specific molecule.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
    • Geometric parameters, including dihedral angles, were precisely measured.

    Main Results:

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    • The crystal structure of C14H10OS was successfully determined.
    • The seven-membered thiepin ring was found to adopt a distorted boat conformation.
    • The dihedral angle between the mean planes of the fused benzene rings was measured as 56.5(1)°.

    Conclusions:

    • The study provides precise structural data for a thiepin derivative.
    • The observed distorted boat conformation offers insights into the flexibility and spatial arrangement of the thiepin ring system.