Triethylphosphine is the

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

with the formula P(CH₂CH₃)₃, commonly abbreviated as PEt₃. It is a colorless liquid with an unpleasant odor characteristic of alkylphosphines. The compound is a common

ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's ele ...

in organometallic chemistry, such as in auranofin.

Structure and simple reactions

It is a

pyramidal A pyramid (from el, πυραμίς ') is a structure whose outer surfaces are triangular and converge to a single step at the top, making the shape roughly a pyramid in the geometric sense. The base of a pyramid can be trilateral, quadrilate ...

molecule with approximate ''C''_3''v'' symmetry. PEt₃ is usually prepared using Grignard reagents: : 3 CH₃CH₂MgCl + P(OC₆H₅)₃ → P(CH₂CH₃)₃ + 3 C₆H₅OMgCl PEt₃ reacts with strong acids to give salts PEt₃.Annette Schier and Hubert Schmidbaur "P-Donor Ligands" in Encyclopedia of Inorganic Chemistry 2006, Wiley-VCH, Weinheim. This reaction is reversible. Similarly, it is also easily alkylated to give

phosphonium In polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, or halide group). These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions. Types of phosphonium c ...

derivatives. PEt₃ is easily oxidised to the phosphine oxide with oxygen.

Coordination chemistry

Triethylphosphine is a highly basic

that forms

coordination complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

es with many metals. As a ligand, triethylphosphine's Tolman cone angle is 132°. Being a relatively compact phosphine, several can bind to a single transition metal, as illustrated by the existence of Pt(PEt₃)₄. As a phosphine ligand, triethylphosphine gained acceptance earlier than did the simpler

trimethylphosphine Trimethylphosphine is a neutral 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 coordi ...

, as illustrated by the preparation of the hydride complex ''trans''-PtHCl(PEt₃)₂. NOZZAF

Safety

PEt₃ is toxic. It converts to a low toxicity

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). Structure and bonding ...

upon treatment with

sodium hypochlorite Sodium hypochlorite (commonly known in a dilute solution as bleach) is an inorganic chemical compound with the formula NaOCl (or NaClO), comprising a sodium cation () and a hypochlorite anion (or ). It may also be viewed as the sodium salt of ...

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3% ...

References

{{reflist Tertiary phosphines Foul-smelling chemicals