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Phosphine oxide : ウィキペディア英語版
Phosphine oxide

Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3). Such compounds are thermally stable, decomposing only above 450 °C.〔D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.〕 Phosphoryl refers to a functional group drawn with a phosphorus-oxygen double bond.
==Structure and bonding==
Phosphine oxides feature tetrahedral phosphorus centers. The P-O bond is short and polar. According to Molecular Orbital Theory, the short P-O bond is attributed to the donation of the lone pair electrons from oxygen p-orbitals to the antibonding phosphorus-carbon bonds; This proposal, which is supported by ''ab initio'' calculations, has gained consensus in the chemistry community.
The nature of the P-O bond was once hotly debated. Some discussions invoked a role for phosphorus-centered d-orbitals in bonding, but this analysis is not supported by computational analyses. In terms of simple Lewis structure, the bond is more accurately represented as a dative bond, as is currently used to depict an amine oxide.

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