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Related Concept Videos

Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

929
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
929
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.6K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.6K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.5K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.7K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.7K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

1.9K
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...
1.9K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.2K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.2K

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Related Experiment Video

Updated: May 30, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Recent advances in antiaromatic metallacycles.

Lei Li1, Yang Li2, Wenfeng Jiang1

  • 1School of Chemistry, Dalian University of Technology, Dalian 116024, P.R. China. baiwei@dlut.edu.cn.

Dalton Transactions (Cambridge, England : 2003)
|January 29, 2025
PubMed
Summary
This summary is machine-generated.

Recent advances reveal new antiaromatic metallacycles, expanding the field of organometallic chemistry. This review covers their synthesis, characterization, and methods for judging antiaromaticity.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry

Background:

  • The study of antiaromaticity in metallacycles is a rapidly developing field.
  • Several novel antiaromatic metallacycles have been synthesized and characterized in recent years.

Purpose of the Study:

  • To review the synthesis and characterization of recently reported antiaromatic metallacycles.
  • To summarize the experimental and theoretical criteria used to assess antiaromaticity in these complexes.

Main Methods:

  • Review of literature on the synthesis and characterization of antiaromatic metallacycles.
  • Analysis of experimental techniques including X-ray crystallography, NMR spectroscopy, and chemical transformations.
  • Evaluation of theoretical methods such as Nuclear Independent Chemical Shift (NICS), Aromatic-like Current Induced by a Dipole (AICD), and Aromaticity/Anti-aromaticity Stabilization Energy (ASE/ISE).

Main Results:

  • Several classes of antiaromatic metallacycles have been successfully synthesized.
  • A combination of experimental and theoretical approaches is typically employed for characterization.
  • Established criteria for judging antiaromaticity include planarity, bond length alternation, NMR chemical shifts, and computational indices.

Conclusions:

  • The field of antiaromatic metallacycles is an emerging area with significant potential for further exploration.
  • A multi-faceted approach combining experimental and theoretical methods is crucial for confirming antiaromaticity.
  • Further research into the synthesis and properties of these compounds will advance our understanding of bonding and electronic structure in organometallic systems.