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 electr ...

organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...

, such as in

auranofin Auranofin is a gold salt classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura. Use Auranofin is used to treat rheumatoid arthritis. It improves arthritis symptoms including painful or tender and ...

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, quadrilater ...

molecule with approximate ''C''_3''v''

symmetry Symmetry (from grc, συμμετρία "agreement in dimensions, due proportion, arrangement") in everyday language refers to a sense of harmonious and beautiful proportion and balance. In mathematics, "symmetry" has a more precise definit ...

. 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 ...

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 In coordination chemistry, the ligand cone angle (a common example being the Tolman cone angle or ''θ'') is a measure of the steric bulk of a ligand in a transition metal coordination complex. It is defined as the solid angle formed with the met ...

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 coordin ...

, as illustrated by the preparation of the

hydride complex Transition metal hydrides are chemical compounds containing a transition metal bonded to hydrogen. Most transition metals form hydride complexes and some are significant in various catalytic and synthetic reactions. The term "hydride" is used loose ...

''trans''-PtHCl(PEt₃)₂. NOZZAF

Safety

PEt₃ is toxic. It converts to a low toxicity phosphine oxide upon treatment with

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

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