1,1,1-Tris(aminomethyl)ethane (TAME) 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. T ...

with the formula CHC(CHNH). It is a colorless liquid. It is classified as a polyamine tripodal ligand, i.e., capable of binding to metal ions through three sites and hence is a tridentate

chelating ligand Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

, 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, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant applicat ...

are potentially explosive, they are excellent and practical source of

primary amines In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent s ...

. The required tris(azidomethyl)ethane is obtained from the tri

tosylate In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on s ...

salt metathesis A salt metathesis reaction, sometimes called a double displacement reaction, is a chemical process involving the exchange of bonds between two reacting chemical species which results in the creation of products with similar or identical bonding a ...

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 ( 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 elec ...

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

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to produce the target Pt(IV) derivatives..

References

{{DEFAULTSORT:Tris(aminomethyl)ethane, 1, 1, 1- Polyamines Tripodal ligands