Trimethylphosphine
chemical compound
Trimethylphosphine is an organophosphorus compound with the formula P(CH3)3, commonly abbreviated as PMe3. This colorless liquid has a strongly unpleasant odor, characteristic of alkylphosphines. The compound is a common ligand in coordination chemistry.
Structure and bonding
It is a pyramidal molecule with approximate C3v symmetry. The C–P–C bond angles are approximately 98.6°.
The C–P–C bond angles are consistent with the notion that phosphorus predominantly uses the 3p orbitals for forming bonds and that there is little sp hybridization of the phosphorus atom. The latter is a common feature of the chemistry of phosphorus. As a result, the lone pair of trimethylphosphine has predominantly s-character as is the case for phosphine, PH3.
PMe3 can be prepared by the treatment of triphenyl phosphite with methylmagnesium chloride:
3 CH3MgCl + P(OC6H5)3 → P(CH3)3 + 3 C6H5OMgCl
The synthesis is conducted in dibutyl ether, from which the more volatile PMe3 can be distilled.
Reactions
With a pKa of 8.65, PMe3 reacts with strong acids to give salts [HPMe3]X. This reaction is reversible.
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