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Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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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 Hückel’s rule or the 4n +...
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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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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.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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...
3.5K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.8K
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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Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

13.4K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
13.4K
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

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Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
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In situ FTIR Spectroscopy as a Tool for Investigation of Gas/Solid Interaction: Water-Enhanced CO2 Adsorption in UiO-66 Metal-Organic Framework
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When Aromaticity Falls Short in Molecule-Surface Interactions.

Jonas Brandhoff1, Richard K Berger2, Felix Otto1

  • 1Institute of Solid State Physics, Friedrich Schiller University Jena, Helmholtzweg 5, Jena 07743, Germany.

The Journal of Physical Chemistry. C, Nanomaterials and Interfaces
|November 26, 2025
PubMed
Summary
This summary is machine-generated.

Molecules can gain aromatic stabilization when adsorbing on surfaces. However, hybridization can outweigh this energetic gain, revealing a new mechanism of dative bonding that alters surface aromatic stabilization.

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Area of Science:

  • Organic Chemistry
  • Surface Science
  • Quantum Chemistry

Background:

  • Aromaticity is a fundamental concept in organic chemistry, driving molecular stabilization.
  • Aromatic stabilization, an energetic gain from increased aromaticity, is observed when molecules adsorb on surfaces.
  • This surface adsorption has been linked to charge transfer into molecular pi-systems.

Purpose of the Study:

  • To investigate alterations in molecular pi-systems upon surface adsorption.
  • To elucidate the influence of adsorption on molecular aromaticity.
  • To explore the interplay between aromatic stabilization and hybridization effects on surfaces.

Main Methods:

  • Photoemission orbital tomography was employed to probe molecular orbitals.
  • Density functional theory (DFT) calculations were utilized to model adsorption and electronic structure.
  • Analysis focused on changes in the molecular pi-system and aromaticity metrics.

Main Results:

  • Surface adsorption can lead to aromatic stabilization, but hybridization effects can counteract this.
  • A novel mechanism involving the formation of dative bonds between the molecular pi-system and the surface was identified.
  • The energetic gains from aromatic stabilization may be offset by hybridization-induced changes.

Conclusions:

  • The concept of aromatic stabilization on surfaces has been incomplete.
  • Surface interactions, including hybridization and dative bonding, significantly modify molecular aromaticity.
  • This study provides a more comprehensive understanding of molecule-surface interactions and aromaticity.