Journal
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS
Volume -, Issue 5, Pages 614-620Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b008789k
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Potentiometric titration in 95% methanol (I=0.1 mol dm(-3), Et4NClO4) has been employed to investigate the effect of N-methylation and N-benzylation of 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 1 on the binding of all three rings to cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II). The results show that enhanced selectivity for silver(I) is exhibited by the di-N-benzylated derivative 3 while the analogous dimethylated derivative 2 discriminates for both silver(I) and lead(II). The crystal structures of [Ag(1)]PF6, [Ag(2)]PF6, [Ag(3)]PF6 and [Pb(1)(NO3)(2)] have been determined. In the silver complexes the NH hydrogens of 1 and the N-methyl and N-benzyl substituents of the dialkylated derivatives 2 and 3 were found to lie on the same side of the mean donor planes of the co-ordinated macrocycles ('cis' arrangements). Density functional theory has been employed to model the silver complexes in both their energy-minimised 'cis' and 'trans' configurations. In accordance with the X-ray evidence, the calculations predict that the 'cis' arrangement is the more stable in each case. The crystal structure of the lead complex of 1 shows a 'trans' arrangement of its NH groups.
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