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BTBPs represent an important class of tetradentate heterocyclic ligands with N-donor binding sites that have been recently developed to separate trivalent actinides from lanthanides. We first investigate by QM calculations the conformational properties, basicity and complexation energies with Eu(NO3)3, comparing BTBP derivatives with alkyl substituents on the pyridinyl or triazinyl moieties to their conformationally cis-locked BTPhen analogues. The latter, preorganized for protonation and complexation, are found to be more basic and to afford more stable complexes. We next explore the interfacial behavior of CyMe4BTBP in its neutral versus protonated states and of 1 [ratio] 1 Eu(NO3)3(CyMe4BTBP) complexes at the aqueous interface with an octanol-hexane mixture. The neutral BTBP ligand displays no visible surface activity, whereas protonated and complexed ligands are surface active. Taken together, the QM and MD results suggest that EuIII extraction by BTBPs occurs at the interface, via the protonated form of the ligand in acidic conditions, explaining why the extraction kinetics is slow and why BTPhen ligands are more efficient than BTBPs.
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