A 4-center 2-electron (4c–2e) bond is a type of

chemical bond A chemical bond is a lasting attraction between atoms or ions that enables the formation of molecules and crystals. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds, or through the sharing o ...

in which four atoms share two

electron The electron ( or ) is a subatomic particle with a negative one elementary electric charge. Electrons belong to the first generation of the lepton particle family, and are generally thought to be elementary particles because they have no kno ...

s in bonding, with a net bond order of . This type of bonding differs from the usual

covalent bond A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atom ...

, which involves two atoms sharing two electrons (2c–2e bonding). Four-center two-electron bonding is postulated in certain

cluster compound In chemistry, an atom cluster (or simply cluster) is an ensemble of bound atoms or molecules that is intermediate in size between a simple molecule and a nanoparticle; that is, up to a few nanometers (nm) in diameter. The term ''microcluster'' ...

s. For instance, the

borane Trihydridoboron, also known as borane or borine, is an unstable and highly reactive molecule with the chemical formula . The preparation of borane carbonyl, BH3(CO), played an important role in exploring the chemistry of boranes, as it indicat ...

anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...

, is a

octahedron In geometry, an octahedron (plural: octahedra, octahedrons) is a polyhedron with eight faces. The term is most commonly used to refer to the regular octahedron, a Platonic solid composed of eight equilateral triangles, four of which meet at ea ...

with an additional proton attached to one of the triangular faces. As a result, the octahedron is distorted and a B–B–B–H

rhomboid Traditionally, in two-dimensional geometry, a rhomboid is a parallelogram in which adjacent sides are of unequal lengths and angles are non-right angled. A parallelogram with sides of equal length (equilateral) is a rhombus but not a 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 and is a relatively new research field, fitting in with the already well established

three-center two-electron bond A three-center two-electron (3c–2e) bond is an electron-deficient chemical bond where three atoms share two electrons. The combination of three atomic orbitals form three molecular orbitals: one bonding, one ''non''-bonding, and one ''anti'' ...

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

tetrahedral In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the ...

geometry.

Tetracyanoethylene Tetracyanoethylene (TCNE) is organic compound with the formula . It is a colorless solid, although samples are often off-white. It is an important member of the cyanocarbons. Synthesis and reactions TCNE is prepared by brominating malononitrile ...

forms a dianionic

dimer Dimer may refer to: * Dimer (chemistry), a chemical structure formed from two similar sub-units ** Protein dimer, a protein quaternary structure ** d-dimer * Dimer model, an item in statistical mechanics, based on ''domino tiling'' * Julius Dimer ( ...

in which the two

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, a ...

s are joined face-to-face by a rectangular four-center two-electron bond. Various solid salts of this dianion have been studied to determine bond strengths and vibrational spectroscopic details.

References

{{DEFAULTSORT:Four-Center Two-Electron Bond Chemical bonding