Four-center two-electron bond

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A four-center two-electron bond is a type of chemical bond in which four atoms share two electrons in bonding which is unusual because in ordinary chemical bonds two atoms share two electrons (2c-2e bonding). This type of bonding is postulated in certain cluster compounds. For instance, the borane B₆H₇^- anion, is a B₆H₆^2- octahedron with an additional proton attached to one of the triangular faces. ^[1]. As a result the octahedron is distorted and a BBBH rhomboid ring can be identified in which this 4c-2e bonding takes place. This type of bonding is associated with electron deficient rhomboid rings in general ^[2] and is a relatively new research field, fitting in with the already well established three-center two-electron bonds and three-center four-electron bonds.

An example of a purely organic compound with four-center two-electron bonding is the adamantyl dication.^[3]

References

^ A new 4c–2e bond in B6H7– Kathrin Hofmann, Marc H. Prosenc and Barbara R. Albert Chem. Commun., 2007, 3097 - 3099, doi:10.1039/b704944g
^ Electron-Deficient Bonding in Rhomboid Rings Musiri M. Balakrishnarajan and Roald Hoffmann J. Am. Chem. Soc.; 2004; 126(40) pp 13119 - 13131; (Article) DOI: 10.1021/ja0467420
^ Matthias Bremer, Paul von Ragué Schleyer, Karl Schötz, Michael Kausch, Michael Schindler Four-Center Two-Electron Bonding in a Tetrahedral Topology. Experimental Realization of Three-Dimensional Homoaromaticity in the 1,3-Dehydro-5,7-adamantanediyl Dication. Angewandte Chemie International Edition in English 1987, 26, 761-763. doi:10.1002/anie.198707611

v • d • e

Chemical bonds

"Strong"

Covalent bonds & Antibonding	Sigma bonds: 3c-2e (bent bond) · 3c-4e (Hydrogen bond, Dihydrogen bond, Agostic interaction) · 4c-2e Pi bonds: p backbonding · Conjugation · Hyperconjugation · Aromaticity · Metal aromaticity Delta bond: Quadruple bond · Quintuple bond · Sextuple bond Coordinate covalent bond · Hapticity

Ionic bonds	Cation-pi interaction · Salt bridge

Metallic bonds	Metal aromaticity

"Weak"

Hydrogen bond	Dihydrogen bond · Dihydrogen complex · Low-barrier hydrogen bond · Symmetric hydrogen bond · Hydrophile

Other noncovalent	van der Waals force · Mechanical bond · Halogen bond · Aurophilicity · Intercalation · Stacking · Entropic force · Chemical polarity

other

Disulfide bond · Peptide bond · Phosphodiester bond

Note: the weakest strong bonds are not necessarily stronger than the strongest weak bonds

Category: Chemical bonding

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