New ligand bearing preorganized binding side-arms interacting with ammonium cations: Synthesis, conformational studies and crystal structureElectronic supplementary information (ESI) available: molecular modeling studies. See http://www.rsc.org/suppdata/nj/b3/b306778e/
2003; Royal Society of Chemistry; Volume: 27; Issue: 11 Linguagem: Inglês
10.1039/b306778e
ISSN1369-9261
AutoresMauro Formica, Vieri Fusi, Luca Giorgi, Annalisa Guerri, Simone Lucarini, Mauro Micheloni, Paola Paoli, Roberto Pontellini, Patrizia Rossi, Giorgio Tarzia, Giovanni Zappia,
Tópico(s)Supramolecular Chemistry and Complexes
ResumoThe synthesis and characterization of the new tetraazamacrocycle 4-(N),10-(N)-bis[2-(3-hydroxy-2-oxo-2H-pyridin-1-yl)acetamido]-1,7-dimethyl-1,4,7,10-tetraazacyclododecane (L) is reported. L shows two 3-(hydroxy)-1-(carbonylmethylen)-2(1H)-pyridinone moieties as side-arms of a tetra-aza-macrocyclic base. The key coupling of side-arms was studied and the most significant results were obtained by activating the 3-(benzyloxy)-1-(carboxymethyl)-2(1H)-pyridinone as pentafluorophenol ester. The acid–base properties of L and its capability to interact with simple ammonium cations were investigated by potentiometric measurements in aqueous solution (298.1 ± 0.1 K, I = 0.15 mol dm−3). Protonated species of L can bind NH4+ or primary ammonium cations such as MeNH3+ discriminating them from secondary or tertiary ammonium cations such as Me2NH2+ or Me3NH+ which are not bound in aqueous solution.
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