N,N’-bis(2-(benzylthio)ethyl)malonamides: Synthesis, Electronic and Steric effects in Silver(I) Extraction and Silver(I) Binding Studies

11 March 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Unsubstituted and 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.


Malonamide derivatives
Job's plot
Mole ratio plot


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