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Tris(2-aminoethyl)amine

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Template:Chembox new Tris(2-aminoethyl)amine is the chemical compound with the formula N(CH2CH2NH2)3. This colourless liquid is soluble in water and is highly basic, consisting of a tertiary amine center and three pendant primary amine groups. Abbreviated "tren," it is the archetypal tripodal ligand of interest in coordination chemistry.

Coordination chemistry

Tren is a tripodal, tetradentate chelating ligand that forms stable complexes with transition metals, especially those in the 2+ and 3+ oxidation states. Tren complexes exist with relatively few isomers, reflecting the constrained connectivity of this tetramine. Thus, only a single achiral stereoisomer exists for [Co(tren)X2]+, where X is halide or pseudohalide.[1] In contrast, for [Co(trien)X2]+ five diastereoiomers are possible, four of which are chiral.

Structures of trigonal bipyramidal and octahedral complexes of the formulae M(tren)X (left, C3v symmetry) and M(tren)X2 (right, Cs symmetry).

The permethylated derivative of tren is also well known. With the formula N(CH2CH2NMe2)3, "Me6tren," forms a variety of complexes but, unlike tren itself, does not stabilize Co(III). Related triphosphines are also well developed, such as N(CH2CH2PPh2)3 (m.p. 101-102 °C). This species is prepared from the nitrogen mustard N(CH2CH2Cl)3.[2]

The tripodal ligand of greatest commercial significance is nitrilotriacetate, N(CH2CO2-)3.

Organic chemistry

Tren is a common impurity in the more common triethylenetetramine ("trien"). As a trifunctional amine, tren forms a triisocyanate when derivatized with COCl2.[3]

Safety considerations

(NH2CH2CH2)3N, like other polyamines, is corrosive.[4] i love aaron newman and i want his bod

References

  1. ^ Donald A. House “Ammonia & N-donor Ligands” in Encyclopedia of Inorganic Chemistry John Wiley & Sons, 2006. doi:10.1002/0470862106.ia009.
  2. ^ R. Morassi, L. Sacconi "Tetradentate Tripod Ligands Containing Nitrogen, Sulfur, Phosphorus, and Arsenic as Donor Atoms" Inorganic Syntheses, 1976, vol. 16 p. 174-180. doi:10.1002/9780470132470.ch47
  3. ^ Pressure Chemical
  4. ^ The Physical and Theoretical Chemistry Laboratory Oxford University MSDS
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