Synthesis of macrocyclic polyamide compounds and studies of their metal ion binding properties

Abstract

Macrocyclic polyamide derivatives containing two nitrogens as donor atoms, 8- membered and pendant arm of nitrobenzo or aminobenzo have been synthesized. The nitrobenzo macroyles, 3,4-(4'-nitrobenzo)-1,6-diazacyclo-octa-3-en-2,5-dione (Ia) and 3,4-(4'-nitrobenzo)-1,6-diazacyclonona-3-en-2,5-dione (IIa), were obtained from condensation of diamine with diacid chloride and reduced to their aminobenzo derivatives, 3,4-(4'-aminobenzo)-1,6-diaza-cycloocta-3-en-2,5-dione (Ib) and 3,4-(4'-aminobenzo)-1,6-diazacyclonona-3-en-2,5-dione (IIb), with H2/Pd. The synthetic products were characterized spectrophotometrically and concluded to contain some water molecules. Their cation binding abilities were investigated by solvent extraction method. Several metals were extracted and their extractabilities varied considerably. The macrocyclic compounds bound effectively with Fe(III), Pb(II) and Na(I) ions. A study of complex formation between Pb(NO3)2' NaNO3 and four synthesized macrocycles indicates 1:1 complexes.