Four-center two-electron bond
Encyclopedia
A four-center two-electron bond is a type of chemical bond
Chemical bond
A chemical bond is an attraction between atoms that allows the formation of chemical substances that contain two or more atoms. The bond is caused by the electromagnetic force attraction between opposite charges, either between electrons and nuclei, or as the result of a dipole attraction...

 in which four atom
Atom
The atom is a basic unit of matter that consists of a dense central nucleus surrounded by a cloud of negatively charged electrons. The atomic nucleus contains a mix of positively charged protons and electrically neutral neutrons...

s share two electron
Electron
The electron is a subatomic particle with a negative elementary electric charge. It has no known components or substructure; in other words, it is generally thought to be an elementary particle. An electron has a mass that is approximately 1/1836 that of the proton...

s 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
Borane
In chemistry, a borane is a chemical compound of boron and hydrogen. The boranes comprise a large group of compounds with the generic formulae of BxHy. These compounds do not occur in nature. Many of the boranes readily oxidise on contact with air, some violently. The parent member BH3 is called...

 B6H7 anion, is a B6H62− octahedron
Octahedral cluster
Octahedral clusters are inorganic or organometallic cluster compounds composed of six metals in an octahedral array. One important class of octahedral clusters are chalcohalide clusters of the type M6X8L6 where M is a metal usually of group 6 or group 7, X is a ligand and more specifically an...

 with an additional proton attached to one of the triangular faces. As a result the octahedron is distorted and a BBBH rhomboid
Rhomboid
Traditionally, in two-dimensional geometry, a rhomboid is a parallelogram in which adjacent sides are of unequal lengths and angles are oblique.A parallelogram with sides of equal length 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
Three-center two-electron bond
A three-center two-electron 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-bonding. The two electrons go into the bonding orbital, resulting in a...

s and three-center four-electron bond
Three-center four-electron bond
The 3-center 4-electron bond is a model used to explain bonding in hypervalent molecules such as phosphorus pentafluoride, sulfur hexafluoride, the xenon fluorides, and the bifluoride ion. It is also known as the Pimentel-Rundle three-center model after the work published by George C. Pimentel in...

s.

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