Triphenylphosphine sulfide (
IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
name: triphenyl-''λ''
5-phosphanethione) is the
organophosphorus compound
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...
with the formula , usually written (where Ph =
phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...
). It is a colourless solid, which is soluble in a variety of organic solvents.
Structurally, the molecule resembles the corresponding oxide, with idealized C
3 point group symmetry
In group theory, the symmetry group of a geometric object is the group of all transformations under which the object is invariant, endowed with the group operation of composition. Such a transformation is an invertible mapping of the ambient ...
. It is weakly
nucleophilic
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they a ...
at the sulfur atom.
Applications
Organic synthesis
Triphenylphosphine sulfide is useful for the conversion of
epoxide
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...
s to the corresponding
episulfides:
:
It also reacts with
ketene
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary valence (chemistry), monovalent functional group, chemical groups (or two separate Substituent, substitution sites in the same molecule). The na ...
s to form
thioketenes:
:
Analytical chemistry
In
analytical chemistry
Analytical skill, Analytical chemistry studies and uses instruments and methods to Separation process, separate, identify, and Quantification (science), quantify matter. In practice, separation, identification or quantification may constitute t ...
, triphenylphosphine is used for the analysis of certain kinds of sulfur compounds. Elemental sulfur (), as occurs in some oils, and labile
organosulfur compounds
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
, such as organic
trisulfides, react with
triphenylphosphine
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a l ...
to give , which can be detected by
gas chromatography
Gas chromatography (GC) is a common type of chromatography used in analytical chemistry for Separation process, separating and analyzing compounds that can be vaporized without Chemical decomposition, decomposition. Typical uses of GC include t ...
.
References
{{reflist
Organophosphine sulfides
Phenyl compounds