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Related Concept Videos

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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).
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

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 annulenes. In...
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Molecular Orbital Theory II03:51

Molecular Orbital Theory II

Molecular Orbital Energy Diagrams

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Related Experiment Video

Updated: Jun 28, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Stacked-ring aromaticity: an orbital model.

D E Bean1, P W Fowler

  • 1Department of Chemistry, The University of Sheffield, S3 7HF, United Kingdom.

Organic Letters
|November 15, 2008
PubMed
Summary
This summary is machine-generated.

Induced current density visualizations reveal that stacking cyclooctatetraene (COT) rings in a superphane reverses antiaromaticity. This phenomenon is driven by through-space interactions and a unique orbital model, quenching paratropicity and inducing diatropic currents.

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Published on: August 22, 2018

Area of Science:

  • Computational Chemistry
  • Theoretical Chemistry
  • Organic Chemistry

Background:

  • Antiaromaticity in [4n]annulenes is a key concept in organic chemistry.
  • Cyclooctatetraene (COT) is a classic example of an antiaromatic system.
  • Superphanes offer unique geometries for studying electronic interactions.

Purpose of the Study:

  • To visualize and demonstrate the reversal of antiaromaticity in stacked COT rings within a superphane.
  • To elucidate the electronic and magnetic origins of this phenomenon.
  • To develop a general orbital model explaining current differences in stacked aromatic and antiaromatic systems.

Main Methods:

  • Utilized the ipsocentric CHF/CTOCD-DZ/6-31G** computational approach.
  • Performed visualization of induced current density.
  • Employed an orbital model for rationalization.

Main Results:

  • Directly demonstrated the reversal of [4n]annulene antiaromaticity upon stacking COT rings into a superphane.
  • Identified through-space interactions leading to a closed-shell electronic structure.
  • Observed quenching of paratropicity in planar COT units.
  • Revealed layered diatropic currents arising from frontier orbital magnetic responses.

Conclusions:

  • The study provides direct visualization supporting the reversal of antiaromaticity in stacked COT superphanes.
  • Through-space interactions significantly alter the electronic and magnetic properties of the system.
  • A general orbital model successfully explains the observed magnetic responses in stacked aromatic and antiaromatic systems.