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Related Concept Videos

Chemical Bonds02:40

Chemical Bonds


Atoms participate in a chemical bond formation to acquire a completed valence-shell electron configuration similar to that of the noble gas nearest to it in atomic number. Ionic, covalent, and metallic bonds are some of the important types of chemical bonds. Bond energy and bond length determine the strength of a chemical bond.
Types of Chemical Bonds
An ionic bond is formed due to electrostatic attraction between cations and anions. Often, the ions are formed by the transfer of electrons from...
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene π orbitals.
Bond Energies and Bond Lengths02:49

Bond Energies and Bond Lengths

Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is bonded to two hydrogen atoms...

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Updated: Jun 10, 2026

A Uniaxial Compression Experiment with CO2-Bearing Coal Using a Visualized and Constant-Volume Gas-Solid Coupling Test System
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Shorter still: compressing C-C single bonds.

Gerardo Martínez-Guajardo1, Kelling J Donald, Bernard K Wittmaack

  • 1Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Col. Noria Alta s/n C.P. 36050, Guanajuato, Gto., México.

Organic Letters
|August 20, 2010
PubMed
Summary
This summary is machine-generated.

Researchers calculated the shortest possible carbon-carbon single bond length, finding it can be compressed to 1.313 Å. This record-breaking bond length results from specific molecular structures minimizing strain and tension.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Investigating the limits of covalent bond lengths is crucial for understanding molecular stability and reactivity.
  • Previous studies have identified short carbon-carbon (C-C) bonds, but the absolute minimum remains an area of exploration.

Purpose of the Study:

  • To determine the shortest achievable C-C single bond length through computational analysis.
  • To explore molecular architectures that facilitate extreme C-C bond compression.

Main Methods:

  • Utilized computational chemistry methods to model and analyze molecular structures.
  • Examined a series of molecules designed to exhibit significant C-C bond shortening.

Main Results:

  • Calculations indicate a C-C single bond can be compressed to 1.313 Å.
  • This represents the shortest C-C single bond length reported to date.
  • Bond shortening is attributed to optimized C-C-C bond angles (θ) that reduce cage strain and bridge tension.

Conclusions:

  • The study establishes a new benchmark for the shortest C-C single bond.
  • Molecular geometry plays a critical role in achieving extreme bond compression.
  • Findings provide insights into the fundamental limits of chemical bonding.