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manuscript for Preprint.docx (1.05 MB)
N,N’-bis(2-(benzylthio)ethyl)malonamides: Synthesis, Electronic and Steric effects in Silver(I) Extraction and Silver(I) Binding Studies
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gem-diethyl substituted malonamide derivatives, bearing benzylthio arms were
prepared in moderate to high yields at room temperature. It was observed that
electronics effects at the 4-aryl position in the malonamide derivatives had a
significant effect on the selectivity, but little effect on silver(I)
extraction efficiency measured by liquid-liquid extraction experiments (with
the 4-methoxy analogue proving the most selective). Increased steric hindrance
near the sulfur donor had a small negative effect on silver(I) extraction
efficiency, while hindrance at the methylene centre reduces selectivity. One of
the malonamide derivatives prepared was found to bind to silver(I) in a 1:1
fashion suggesting a tetrahedral coordination type.