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Related Concept Videos

Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.4K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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.
7.8K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.1K
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.
3.1K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

1.4K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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1,4-Digermacyclopenta-1,3-diene: Continuous Cyclic σ*-π Delocalization Enables Aromatic Stabilization in a

Daichi Uchida1, Hiroko Yamada1, Yoshiyuki Mizuhata1

  • 1Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, Japan.

Angewandte Chemie (International Ed. in English)
|April 25, 2026
PubMed
Summary
This summary is machine-generated.

Heavy-element systems exhibit unique aromaticity via cyclic electron delocalization. Researchers discovered 1,4-digermacyclopenta-1,3-diene, an aromatic compound stabilized by sigma-star to pi interactions.

Keywords:
aromaticitycyclic delocalizationgermaniumheavy‐element π systemsσ*–π delocalization

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Area of Science:

  • Inorganic Chemistry
  • Theoretical Chemistry
  • Materials Science

Background:

  • Aromaticity in heavier elements offers unique electronic properties.
  • Unconventional cyclic electron delocalization is key to understanding these systems.

Purpose of the Study:

  • To investigate the aromatic nature of 1,4-digermacyclopenta-1,3-diene.
  • To elucidate the role of sigma-star to pi interactions in stabilizing this heavy-element system.

Main Methods:

  • X-ray crystallography for structural determination.
  • Magnetic and electronic analyses including Nucleus-Independent Chemical Shift (NICS), Galvanomagnetic Intermolecular Current (GIMIC), Aromaticity in Cyclic Systems (ACID), and Electron-Delocalization Degree in Bonds (EDDB).
  • Natural Bond Orbital (NBO) analysis for electronic structure investigation.

Main Results:

  • A nearly planar [Ge2C3] ring structure was confirmed via X-ray crystallography.
  • Consistent indicators of significant aromatic stabilization were observed through various magnetic and electronic analyses.
  • GIMIC calculations revealed a strong diatropic ring current (+8.38 nA T^-1), confirming aromaticity.
  • NBO analysis identified sigma-star to pi delocalization involving the Ge-Ge bond as the primary stabilization mechanism.

Conclusions:

  • 1,4-digermacyclopenta-1,3-diene exhibits significant aromatic stabilization through unconventional sigma-star to pi interactions.
  • This system represents a rare example of continuous cyclic delocalization facilitated by sigma-star to pi interactions in heavy-element compounds.
  • The compound remains predominantly closed-shell despite a minor open-shell contribution, highlighting a distinct mode of aromatic stabilization.