Phosphine

A phosphorus-centered compound with three substituents and a lone pair, commonly represented as PR₃. Phosphines are used as ligands and reagents in synthesis.

Phosphorus: A chemical element with atomic number 15, found in several allotropes and widely used in biology and industry. Phosphine’s central atom is phosphorus, whose bonding permits three substituents and a lone pair.
Lewis base: A species that donates an electron pair to form a bond. Phosphines use phosphorus’s lone pair to bind electrophiles and metal centers.
Wilkinson's catalyst: A rhodium–phosphine complex that catalyzes the hydrogenation of alkenes. Its triphenylphosphine ligands illustrate phosphines’ role in homogeneous catalysis.
Phosphite: A phosphorus(III) compound commonly containing P–O–R bonds, including trialkyl phosphites. Phosphites resemble phosphines as phosphorus(III) donors but contain oxygen substituents.
Trimethylphosphine: A volatile organophosphorus compound with three methyl groups bonded to phosphorus. Its small alkyl substituents make it a compact example of a trialkylphosphine.
Lewis structure: A diagram showing valence electrons and bonds in a molecule or ion. A Lewis structure makes phosphine’s three P–R bonds and phosphorus lone pair explicit.
Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group at an electrophilic center. Phosphines attack suitable electrophiles, forming phosphonium intermediates in substitution reactions.
Buchwald–Hartwig amination: A palladium-catalyzed coupling that forms carbon–nitrogen bonds from aryl halides and amines. Phosphine ligands help tune the palladium catalysts used for this coupling.
Phosphine ligand: A phosphine molecule coordinated to a metal through the phosphorus lone pair. Coordination changes phosphine’s role from free reagent to bound component of a metal complex.
Triethylphosphine: An organophosphorus compound with three ethyl groups bonded to phosphorus. It shows how changing alkyl substituents alters a phosphine’s steric and electronic properties.

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