What is "trisamine"

Tris(benzyltriazolylmethyl)amine (TBTA) is a tertiary amine containing the 1,2,3-triazole moiety. When used as a ligand, complexed to copper(I), it allows for quantitative, regioselective formal Huisgen 1,3-dipolar cycloadditions between alkynes and azides, in a variety of aqueous and organic solvents.

It is believed that the ligand promotes catalysis through the stabilization of the copper(I)-oxidation state, while still allowing for the catalytic cycle of the CuAAC reaction to proceed.

Single crystal X-ray diffraction of the Cu(I) complex of tris(benzyltriazolylmethyl)amine revealed an unusual dinuclear dication with one triazole unit bridging two metal centers, and is an effective catalyst for the 'click' cycloaddition reaction. The structure of the complex of TBTA with Cu(II) in the crystalline state is trigonal bipyramidal and can be reduced to the active 'click' catalyst form by sodium ascorbate, copper metal, or other reducing agents.

In the literature, it has been gaining widespread use as a biochemical tool for the tagging of proteins and enzymes. The compound is now commercially available through Sigma-Aldrich and Invitrogen. It may be prepared by the click reaction between tripropargylamine and benzyl azide:

Tris(2-aminoethyl)amine is the organic compound with the formula N(CHCHNH). 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.

Tren is a C3-symmetric, 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)X], where X is halide or pseudohalide. In contrast, for [Co(trien)X] five diastereomers are possible, four of which are chiral. In a few cases, tren serves as a tridentate ligand with one of the primary amine groups non-coordinated.

Tris(2-pyridylmethyl)amine (abbreviated TPMA or TPA) is an organic compound with the formula (CHNCH)N. 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.

The ligand is prepared by the alkylation of picolylamine by picolyl chloride:

2 CHNCHCl + CHNCHNH → (CHNCH)N + 2 HCl

TPA is a tripodal ligand, often used to simulate the coordination environment within some proteins. It is also used as a copper ligand in ATRP. A related ligand is dipicolylamine, which in fact is an intermediate in the synthesis of TPA.