Triphenylarsine is the
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula As(C
6H
5)
3. This
organoarsenic compound
Organoarsenic chemistry is the chemistry of Chemical compound, compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herb ...
, often abbreviated As
Ph3, is a colorless crystalline solid that is used as a ligand and a reagent in
coordination chemistry
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...
and
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.
This compound is prepared by the
Wurtz reaction of
arsenic trichloride with
chlorobenzene
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent a ...
using
sodium
Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...
as the reducing agent:
[article]
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:AsCl3 + 3 PhCl + 6 Na → AsPh3 + 6 NaCl
Reactions
Reaction of triphenylarsine with lithium gives lithium diphenylarsenide and phenyllithium
Phenyllithium is an organometallic agent with the empirical formula . It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyl ...
:
:AsPh3 + 2 Li → LiAsPh2 + LiPh
Triphenylarsine is the precursor to tetraphenylarsonium chloride, sPh4l, a popular precipitating agent.[
AsPh3 forms ]metal complex
A coordination complex is a chemical compound consisting 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 ...
es with metals. Most are analogues of the corresponding triphenylphosphine derivatives. Examples include rCl(CO)(AsPh3)sub>2, hCl(AsPh3)3 and e(CO)4(AsPh3)Tetraphenylarsonium chloride
Tetraphenylarsonium chloride is the organoarsenic compound with the formula (C6H5)4AsCl. This white solid is the chloride salt of the tetraphenylarsonium cation, which is tetrahedral. Typical of related quat salts, it is soluble in polar organic ...
is prepared from triphenylarsine:
References
{{reflist
Phenyl compounds
Organoarsenic compounds