1,1,1-Tris(aminomethyl)ethane (TAME) is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula CHC(CHNH). It is a colorless liquid. It is classified as a
polyamine tripodal ligand
Tripodal ligands are tridentate, 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 ...
, i.e., capable of binding to metal ions through three sites and hence is a tridentate
chelating ligand, occupying a face of the coordination polyhedron.
Preparation
TAME is synthesized by the Pd/C-catalyzed hydrogenation of 1,1,1-tris(azidomethyl)ethane. Although
azides
In chemistry, azide (, ) is a Linear molecular geometry, linear, polyatomic anion with the Chemical formula, formula and Chemical structure, structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the ...
are potentially explosive, they are excellent and practical source of
primary amines. The required tris(azidomethyl)ethane is obtained from the tri
tosylate by
salt metathesis using
sodium azide. These two steps are:
:3 NaN + CHC(CHOTs) → CHC(CHN) + 3 NaOTs
:3 H + CHC(CHN) → CHC(CHNH) + 3 N
Complexes of TAME
The tripodal TAME
ligand
In coordination chemistry, a ligand is an ion or molecule with a 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 el ...
coordinates facially to metal ions. This stereochemical feature has been exploited in the preparation of platinum(IV) cage complexes, e.g.,
t(tame) which is a six coordinate Pt(IV) complex. Platinum in its +4 oxidation state has a d configuration and is kinetically inert. For this reason the formation of
t(tame)is initiated by installing TAME on a platinum(II) precursor. The resulting square planar complex is oxidized with
tClto produce the target Pt(IV) derivatives.
[.]
References
{{DEFAULTSORT:Tris(aminomethyl)ethane, 1, 1, 1-
Polyamines
Tripodal ligands