Four-center two-electron bond

A four-center two-electron bond is a type of chemical bond in which four atoms share two electrons in bonding, with a net bond order of ½. This type of bonding differs from the usual covalent bond, which involves two atoms sharing two electrons (2c-2e bonding).

Four-center two-electron bonding is postulated in certain cluster compounds. For instance, the borane B
anion, is a B
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 bond.

An example of a purely organic compound with four-center two-electron bonding is the adamantyl dication.[3] The bond joins the four bridgehead atoms in a tetrahedral geometry.

Tetracyanoethylene forms a dianionic dimer in which the two alkenes are joined face-to-face by a rectangular four-center two-electron bond.[4] Various solid salts of this dianion have been studied to determine bond strengths and vibrational spectroscopic details.[5]


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