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

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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...
Valence Bond Theory02:42

Valence Bond Theory

Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...
Crystal Field Theory - Tetrahedral and Square Planar Complexes02:46

Crystal Field Theory - Tetrahedral and Square Planar Complexes

Tetrahedral Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

You might also read

Related Articles

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

Sort by
Same author

Direct Conversion of Metal Carbonates and Bicarbonates to Methanol Over a Cu/ZnO/Al<sub>2</sub>O<sub>3</sub> Catalyst.

ChemSusChem·2026
Same author

Unveiling Superacidity in Alcohol-BF<sub>3</sub> Complexes Using a Vibrational Probe.

The journal of physical chemistry letters·2026
Same author

Great strides, yet a long way to go: a comparative analysis of WASH conditions and associated sociodemographic factors from national hygiene surveys, 2014 and 2018.

Global health action·2026
Same author

Synergistic Organophotoredox and Copper Catalysis Enabling the Difluoromethylation of Alkyl Bromides.

Organic letters·2025
Same author

Improved CO<sub>2</sub> conversion to methanol promoted by ionic liquid additives using a Cu/ZnO/Al<sub>2</sub>O<sub>3</sub> heterogeneous catalyst.

Chemical communications (Cambridge, England)·2025
Same author

Climate change scenario in Bangladesh: historical data analysis and future projection based on CMIP6 model.

Scientific reports·2025

Related Experiment Video

Updated: May 27, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

C7H12(2+): a prototype hexacoordinate carbonium ion.

Golam Rasul1, George A Olah, G K Surya Prakash

  • 1Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661, USA. rasul@usc.edu

The Journal of Physical Chemistry. A
|December 2, 2011
PubMed
Summary

Researchers identified the hexacoordinate carbonium dication C(7)H(12)(2+) as a stable minimum. This propeller-shaped molecule forms three two-electron, three-center bonds with ethylene, with a more stable isomer identified.

More Related Videos

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations
13:56

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations

Published on: October 12, 2019

Related Experiment Videos

Last Updated: May 27, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations
13:56

Probe Type II Band Alignment in One-Dimensional Van Der Waals Heterostructures Using First-Principles Calculations

Published on: October 12, 2019

Area of Science:

  • Computational chemistry
  • Quantum chemistry
  • Organic chemistry

Background:

  • Hexacoordinate carbonium dications represent a novel class of chemical species.
  • Understanding their stability and bonding is crucial for advancing chemical theory.

Purpose of the Study:

  • To computationally investigate the structure and stability of the prototype hexacoordinate carbonium dication C(7)H(12)(2+).
  • To explore isomeric structures and their relative energies.
  • To examine the potential energy surface for interconversion between isomers.

Main Methods:

  • Ab initio calculations using the MP2//6-31G** and MP2//cc-pVTZ levels of theory.
  • Geometry optimization to locate minima and transition states.
  • Energy calculations to determine relative stability and reaction barriers.

Main Results:

  • The hexacoordinate carbonium dication C(7)H(12)(2+) (structure 1) was found to be a stable minimum.
  • Structure 1 exhibits a propeller-like conformation with three two-electron, three-center (2e-3c) bonds.
  • An isomeric structure (2) was found to be more stable than structure 1 by 21.8 kcal/mol, with a conversion barrier of 5.7 kcal/mol.
  • Additional related minima (4, 5, 8) for C(7)H(12)(2+) were identified.
  • The isoelectronic analogue BC(6)H(12)(+) (10) was also computed as a minimum.

Conclusions:

  • The hexacoordinate carbonium dication C(7)H(12)(2+) is a chemically viable species.
  • The bonding in C(7)H(12)(2+) involves novel three-center bonding arrangements.
  • Computational methods provide valuable insights into the structure and reactivity of unusual chemical species.