PMDTA
chemical compound
PMDTA (N,N,N′,N′′,N′′-pentamethyldiethylenetriamine) is an organic compound with the formula [(CH3)2NCH2CH2]2NCH3. PMDTA is a basic, bulky, and flexible, tridentate ligand that is used in organolithium chemistry. It is a colorless liquid, although impure samples appear yellowish.
Synthesis
PMDTA is prepared from diethylenetriamine by the Eschweiler-Clarke reaction, involving the use of formaldehyde and formic acid.
(H2N[CH2]2)2NH + 5 CH2O + 5 HCO2H → (Me2N[CH2]2)2NMe + 5 CO2 + 5 H2O
Comparison with diethylenetriamine
Unlike diethylenetriamine, all three amines in PMDTA are tertiary. Both PMDTA and diethylenetriamine are tridentate ligands that form two five-membered chelate rings. The σ-donating properties of the amino groups of diethylenetriamine are greater than that of PMDTA in copper(II) complexes. Both ligands can coordinate metal complexes in arrangements where the three nitrogen centers are co-planar or mutually cis.
Organolithium compounds and PMDTA
PMDTA is used to modify the reactivity of organolithium compounds, which deaggregate in the presence of Lewis bases to enhance their reactivity. Commonly, the ditertiary amine TMEDA is used in these applications; it binds to the lithium center as a bidentate ligand.
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