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Related Concept Videos

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...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Newman Projections02:06

Newman Projections

Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as conformers.
Coplanar Forces01:25

Coplanar Forces

Consider an object upon which multiple forces are acting. If the lines of action of each force lie within the same plane, the system can be considered coplanar. The Cartesian vector form can be used to resolve each force into its respective components. For a coplanar system, the system will be in equilibrium if each component of the resultant force equals zero and the resultant force on the system is zero. If the sum of the forces is not equal to zero, then the object will not be in equilibrium...
Carbon Skeletons01:12

Carbon Skeletons

Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side chains...

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Related Experiment Video

Updated: Jul 3, 2026

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids (BPCA)
08:12

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids (BPCA)

Published on: May 16, 2016

Planar pentacoordinate carbon in CAl5(+): a global minimum.

Yong Pei1, Wei An, Keigo Ito

  • 1Department of Chemistry and Nebraska Center for Materials and Nanoscience, University of Nebraska-Lincoln, Lincoln, Nebraska 68588, USA.

Journal of the American Chemical Society
|July 11, 2008
PubMed
Summary

Researchers discovered the first planar pentacoordinate carbon structure in the CAl5(+) cation. This stable, two-dimensional chemical bonding arrangement is a significant finding in computational chemistry.

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Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
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Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

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Published on: May 16, 2016

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
12:11

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Area of Science:

  • Computational Chemistry
  • Quantum Mechanics
  • Materials Science

Background:

  • Pentacoordinate carbon is rare and typically nonplanar.
  • Exploring novel bonding configurations is crucial for chemical innovation.

Purpose of the Study:

  • To identify and characterize the global minimum structure of the CAl5(+) cation.
  • To investigate the stability and bonding properties of planar pentacoordinate carbon.

Main Methods:

  • High-level ab initio computations.
  • Quantum molecular dynamics simulations at 300 K and 400 K.

Main Results:

  • The most stable CAl5(+) isomer exhibits D5h symmetry, featuring a planar pentacoordinate carbon.
  • This isomer is energetically favored by 3.80 kcal/mol over nonplanar alternatives.
  • The planar structure demonstrates robust thermal stability and a high propensity for 2D chemical bonding.

Conclusions:

  • The D5h CAl5(+) cation represents the first observed global-minimum structure with a planar pentacoordinate carbon.
  • Computational findings suggest experimental characterization at room temperature is feasible.
  • This discovery opens new avenues for exploring 2D chemical bonding and novel carbon structures.