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Related Concept Videos

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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.
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
[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: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

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Related Experiment Video

Updated: Jun 5, 2026

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

Mustafa Tombul, Adnan Bulut, Kutalmış Güven

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    This study reveals that in the [Fe(2)(C(5)H(5))(2)(C(14)H(12)O(2))] crystal structure, carbonyl groups align with cyclopentadienyl rings. This maximizes electronic interactions and results in C-H⋯O contacts.

    Area of Science:

    • Organometallic Chemistry
    • Crystallography

    Background:

    • Understanding the structural and electronic properties of organometallic compounds is crucial for developing new materials.
    • The interplay between organic ligands and metal centers dictates the reactivity and physical characteristics of these complexes.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, [Fe(2)(C(5)H(5))(2)(C(14)H(12)O(2))].
    • To investigate the electronic interactions and intermolecular forces within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
    • Analysis of bond distances, angles, and intermolecular contacts was performed.

    Main Results:

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  • The crystal structure analysis revealed that each carbonyl group is coplanar with the adjacent cyclopentadienyl ring.
  • This coplanarity maximizes π-orbital overlap and electronic interactions between these moieties.
  • Intermolecular and intramolecular C-H⋯O contacts were identified within the crystal structure.

    • Conclusions:

    • The observed structural arrangement in [Fe(2)(C(5)H(5))(2)(C(14)H(12)O(2))] facilitates significant electronic communication.
    • The presence of C-H⋯O contacts influences the overall crystal packing and stability.