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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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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...
3.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
3.1K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.0K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.0K
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

4.7K
An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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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,...
4.4K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.3K
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...
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Aromaticity in a Palladium-Capped Al6 Trigonal Prismatic Cluster.

Pengfei Chen1, Jiaxin Chen2, Yue Zhao1

  • 1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.

Journal of the American Chemical Society
|June 5, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized the first all-metal aluminum cluster exhibiting aromaticity. This trigonal prismatic structure, capped with palladium, expands the understanding of aromaticity in inorganic systems.

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Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Quantum Chemistry

Background:

  • Aromaticity is crucial for molecular stability, primarily studied in organic chemistry.
  • All-metal aromaticity, proposed two decades ago in aluminum clusters, remains challenging to isolate and characterize.

Purpose of the Study:

  • To synthesize and characterize the first all-metal aluminum cluster with aromatic properties.
  • To investigate the structural and electronic characteristics of this novel cluster.

Main Methods:

  • X-ray crystallography for structural determination.
  • Quantum chemical calculations to probe electronic structure and bonding.
  • Synthesis of a novel palladium-capped aluminum cluster.

Main Results:

  • Isolation and characterization of a unique Al6 trigonal prismatic cluster capped by palladium atoms.
  • Identification of three 3c-2e σ bonds and a novel 6c-2e π-π interacting bond.
  • Quantum chemical calculations confirm aromaticity in the Pd-capped Al6 cluster.

Conclusions:

  • The study presents the first example of an all-metal aromatic polyhedral aluminum cluster.
  • This discovery broadens the scope of aromaticity beyond traditional organic systems.
  • Opens new avenues for designing and synthesizing novel all-metal aromatic compounds.