Tris(2-pyridylmethyl)amine (abbreviated TPMA or TPA) is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (C
5H
4NCH
2)
3N. It is a tertiary amine with three
picolyl substituents. It is a white solid that is soluble in polar organic solvents. It is a
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 ...
in
coordination chemistry
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 ...
.
The ligand is prepared by the alkylation of
2-picolylamine
2-Picolylamine is an organic compound with the formula H2NCH2C5H4N. A colorless liquid, it is a common bidentate ligand and a precursor to more complex multidentate ligands such as tris(2-pyridylmethyl)amine. It is usually prepared by hydrogenat ...
by picolyl chloride:
[{{cite book , author1=James W. Canary , author2=Yihan Wang , author3=Richard Roy, Jr. , title = Tris 2-Pyridyl)MethylAmine (TPA) and (+)-Bis 2-Pyridyl)methyl1-(2-Pyridyl)-Ethylamine (α-Metpa) , journal = ]Inorg. Synth.
''Inorganic Syntheses'' is a book series which aims to publish "detailed and foolproof" procedures for the synthesis of inorganic compounds.tripodal ligand
Tripodal ligands are tri- and tetradentate ligands. They are popular in research in the areas of coordination chemistry and homogeneous catalysis. Because the ligands are polydentate, they do not readily dissociate from the metal centre. Many trip ...
, often used to simulate the coordination environment within some proteins. It is also used as a copper
Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkis ...
ligand in ATRP.
Related ligands
* dipicolylamine, an intermediate in the synthesis of TPMA.
*2-picolylamine
2-Picolylamine is an organic compound with the formula H2NCH2C5H4N. A colorless liquid, it is a common bidentate ligand and a precursor to more complex multidentate ligands such as tris(2-pyridylmethyl)amine. It is usually prepared by hydrogenat ...
, a bidentate ligand, also known as aminomethylpyridine.
References
Tripodal ligands
Amines
2-Pyridyl compounds