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Related Concept Videos

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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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).
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NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

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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 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...
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Capturing coherent pseudorotation through conical intersection in photoionized benzene.

Zejin Liu1, Ming Zhang2,3, Tianyu Zhou4

  • 1Institute of Atomic and Molecular Physics and Jilin Provincial Key Laboratory of Applied Atomic and Molecular Spectroscopy, Jilin University, Changchun, China.

Nature Communications
|December 16, 2025
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Summary

We observed a long-lasting oscillation in photoionized benzene, revealing pseudorotation of the benzene cation. This motion arises from quantum beating between vibronic states, offering insights into molecular dynamics.

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Area of Science:

  • Physical Chemistry
  • Molecular Dynamics
  • Quantum Mechanics

Background:

  • Vibronic coupling and coherence are fundamental to charge and energy transfer in photoexcited molecules.
  • Understanding coupled electron-nuclear dynamics is key to controlling molecular processes.

Purpose of the Study:

  • To investigate the coupled electron-nuclear dynamics of photoionized benzene.
  • To characterize the origin of observed long-period oscillations in ion yields.

Main Methods:

  • Time-resolved Coulomb-explosion imaging technique.
  • Quantum dynamics simulations.
  • Analysis of ion yields and momentum distributions.

Main Results:

  • Experimental observation of a ~600 fs oscillation in ion yields for benzene cation.
  • Quantum simulations attribute oscillation to pseudorotation of the benzene cation.
  • Identification of quantum beating between coherent vibronic states via Jahn-Teller effect.

Conclusions:

  • The study provides a comprehensive characterization of coherent vibronic dynamics in the benzene cation.
  • Pseudorotation is visualized through time-resolved momentum imaging of Coulomb explosion fragments.
  • Time-resolved Coulomb-explosion imaging is a powerful tool for studying coupled electronic-nuclear motion in aromatic molecules.