Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

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...
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).
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.
VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry
VSEPR Theory and the Basic Shapes02:52

VSEPR Theory and the Basic Shapes

Overview of VSEPR Theory

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Modular Framework for 3D Molecular Generation in Computational Chemistry Applications.

Journal of the American Chemical Society·2026
Same author

A Borane Sandwich Analogue of Ferrocene.

Angewandte Chemie (International ed. in English)·2026
Same author

Benchmarking physics-inspired machine learning models for transition metal complexes with diverse charge and spin states.

Digital discovery·2026
Same author

Ligand rigidity as a design principle for planar pentacoordinate fluorine.

Chemical communications (Cambridge, England)·2026
Same author

Advancing Reproducibility and Open Data in Theoretical and Computational Chemistry.

Journal of chemical theory and computation·2026
Same author

NaviDiv: a web app for monitoring chemical diversity in generative molecular design.

Digital discovery·2026
Same journal

Lower bound of the capacitance of constant phase elements based on electrochemical impedance spectra.

Physical chemistry chemical physics : PCCP·2026
Same journal

Stability constants of lanthanide-nitrate complexes in aqueous solutions: a theoretical study.

Physical chemistry chemical physics : PCCP·2026
Same journal

Lead-free Cs<sub>3</sub>MnCl<sub>5</sub> and CsMnCl<sub>3</sub> crystals: rapid on-chip crystallization, phase transition and fluorescence sensing applications.

Physical chemistry chemical physics : PCCP·2026
Same journal

F-Interstitial passivation preserves host-like optoelectronic properties in <sup>229</sup>Th:YLF nuclear-clock platforms.

Physical chemistry chemical physics : PCCP·2026
Same journal

Structural trends of tryptophan dimer: hydrogen bonding <i>versus</i> π-stacking from an energy decomposition analysis perspective.

Physical chemistry chemical physics : PCCP·2026
Same journal

Achieving high thermoelectric performance in Sb<sub>2</sub>Se<sub>3</sub>-alloyed GeTe through synergistic optimization of electrical and thermal transport.

Physical chemistry chemical physics : PCCP·2026
See all related articles

Related Experiment Video

Updated: May 29, 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

Can an eight π-electron bare ring be planar?

Gerardo Martinez-Guajardo1, Zeferino Gómez-Saldoval, Daniel F Jana

  • 1Departamento de Química, Universidad de Guanajuato, Noria Alta s/n C.P. 36050, Guanajuato, Gto, Mexico.

Physical Chemistry Chemical Physics : PCCP
|September 10, 2011
PubMed
Summary
This summary is machine-generated.

Researchers explored silicon, germanium, and tin substitutions in cyclooctatetraene rings. Planar eight π-electron systems were achieved, enhancing delocalization energy compared to the original ring.

More Related Videos

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
06:56

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
08:18

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Published on: March 4, 2021

Related Experiment Videos

Last Updated: May 29, 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

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
06:56

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
08:18

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Published on: March 4, 2021

Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Cyclooctatetraene (cot) is a non-planar, eight π-electron system.
  • Achieving planar, delocalized π-electron systems is key for novel electronic properties.

Purpose of the Study:

  • To investigate in silico the feasibility of creating planar eight π-electron ring systems.
  • To explore substitutions of carbon atoms in cyclooctatetraene with heavier Group 14 elements.

Main Methods:

  • In silico computational modeling.
  • Systematic substitution of carbon atoms in cyclooctatetraene with silicon, germanium, and tin.

Main Results:

  • Identified stable, planar eight-membered rings with formulas C(4)Si(4)H(8), C(4)Ge(4)H(8), and C(4)Sn(4)H(8).
  • These substituted rings exhibit enhanced delocalization energy compared to unsubstituted cyclooctatetraene.

Conclusions:

  • Heavier Group 14 elements can be incorporated into cyclooctatetraene frameworks to yield stable, planar π-electron systems.
  • These findings offer a new pathway for designing novel conjugated materials with tunable electronic properties.