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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.3K
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...
4.3K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

2.0K
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...
2.0K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

6.1K
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,...
6.1K
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.7K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred...
2.7K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

13.8K
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).
13.8K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.3K
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...
4.3K

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Related Experiment Video

Updated: Apr 5, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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PtZnH5(-), A σ-Aromatic Cluster.

Xinxing Zhang1, Gaoxiang Liu1, Gerd Ganteför1

  • 1†Department of Chemistry and Materials Science, Johns Hopkins University, Baltimore, Maryland 21218, United States.

The Journal of Physical Chemistry Letters
|August 14, 2015
PubMed
Summary
This summary is machine-generated.

We discovered a unique PtZnH5(-) cluster with planar pentagonal platinum, showing unusual stability due to σ-aromaticity. This finding advances understanding of transition-metal hydrides and their catalytic potential.

Keywords:
cluster hydridesphotoelectron spectroscopytheoryσ-aromaticity

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Area of Science:

  • Inorganic Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Mixed transition-metal hydrides are crucial in catalysis.
  • Understanding cluster stability is key for designing new materials.
  • Aromaticity in hydrogen systems is theoretically predicted but experimentally elusive.

Purpose of the Study:

  • To investigate the structure and stability of the PtZnH5(-) cluster anion.
  • To explore the role of σ-aromaticity in stabilizing transition-metal hydride clusters.
  • To provide experimental and theoretical insights into unprecedented cluster geometries.

Main Methods:

  • Joint photoelectron spectroscopy was employed for experimental characterization.
  • Quantum chemical calculations were performed for theoretical analysis.
  • Mass spectrometry was used to assess cluster intensity and stability.

Main Results:

  • The PtZnH5(-) cluster exhibits an unprecedented planar pentagonal coordination for platinum.
  • Unusual stability and high intensity were observed in the mass spectrum.
  • The stability is attributed to σ-aromaticity within the H5-cycle, supported by Pt 5d orbitals.

Conclusions:

  • The study provides the first experimental observation of σ-aromaticity in an all-hydrogen system.
  • The findings highlight the potential of σ-aromaticity to stabilize mixed transition-metal hydrides.
  • This research has implications for fundamental chemistry and practical applications in catalysis.