Carborane

A polyhedral cluster compound containing carbon, boron, and hydrogen, with carbon and boron atoms forming a stable cage. Its delocalized bonding gives many carboranes unusual stability and distinctive chemical behavior.

Icosahedral closo-carboranes: Carborane clusters with an icosahedral cage of twelve vertices and a closed-shell electron count. The best-known carboranes adopt this highly stable cage geometry.
Deboronation: A chemical transformation that removes boron atoms from a boron-containing molecule or cluster. Removing a cage boron can convert closo-carboranes into nido clusters.
Boron neutron capture therapy: A cancer treatment strategy that irradiates boron-10 in tumors with neutrons to produce cell-damaging particles. Carboranes can carry high boron payloads into boron neutron capture therapy candidates.
Metallacarboranes: Cluster compounds in which a metal atom occupies one or more vertices of a carborane-related cage. Replacing a cage vertex with a metal distinguishes these compounds from carboranes.
Skeletal electron pair theory: A framework for relating cluster shapes to the electron pairs used in skeletal bonding. It accounts for the electron requirements behind carborane cage structures.
Cage-opening reaction: A reaction that breaks one or more skeletal bonds in a polyhedral cluster. Carborane cages can open under selected conditions and form less-closed clusters.
Boron neutron capture therapy agents: Molecules designed to deliver boron-10 selectively to tumors for neutron-capture treatment. Carborane cages are investigated as compact, boron-rich components of these agents.
Heteroboranes: Boron cluster compounds containing one or more skeletal atoms other than boron and hydrogen. Carboranes are a prominent carbon-containing branch of this broader cluster family.
Wade's rules: Electron-counting rules that predict structures of many borane and related clusters. These rules help predict which carborane cage geometries are stable.
Electrophilic aromatic substitution: A substitution reaction in which an electrophile replaces hydrogen on an aromatic ring. Carborane carbon vertices can undergo substitution, but their cage bonding is not ordinary aromatic-ring chemistry.

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