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Related Concept Videos

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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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.8K
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.
2.8K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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...
2.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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...
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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.1K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.1K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.0K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
11.0K

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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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φ-Aromaticity in prismatic {Bi6}-based clusters.

Benjamin Peerless1,2, Andreas Schmidt1,2, Yannick J Franzke3

  • 1Fachbereich Chemie, Philipps-Universität Marburg, Marburg, Germany.

Nature Chemistry
|December 22, 2022
PubMed
Summary

Researchers discovered a new type of aromaticity, termed φ-aromaticity, in all-metal bismuth (Bi) clusters. Regular bismuth prisms exhibit this unique electronic behavior, unlike distorted structures, advancing the understanding of metallic aromaticity.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Area of Science:

  • * Inorganic Chemistry
  • * Materials Science
  • * Quantum Chemistry

Background:

  • * Aromaticity is well-established in organic molecules.
  • * All-metal molecules can exhibit σ- and π-aromaticity.
  • * Electron mobility in all-metal compounds extends beyond traditional axes.

Purpose of the Study:

  • * To investigate novel aromaticity in purely metallic systems.
  • * To explore the electronic properties of bismuth clusters.
  • * To identify conditions favoring or inhibiting φ-aromaticity.

Main Methods:

  • * Experimental synthesis of heterometallic bismuth clusters.
  • * Quantum chemical calculations.
  • * Analysis of molecular orbital symmetry and ring currents.

Main Results:

  • * Regular {Bi6} prisms exhibit f-type molecular orbitals and strong ring currents.
  • * This behavior defines a new form of aromaticity: φ-aromaticity.
  • * The heterometallic cluster [{CpRu}3Bi6]- displays φ-aromaticity.
  • * A hypothetical Bi62- prism also shows φ-aromaticity.
  • * Distorted Bi6 moieties in [{(cod)Ir}3Bi6] inhibit φ-aromaticity.

Conclusions:

  • * Regular prismatic bismuth clusters can exhibit φ-aromaticity.
  • * This discovery expands the concept of aromaticity to purely metallic systems.
  • * Molecular geometry is crucial for the manifestation of φ-aromaticity.