Competition between coordination bonds and hydrogen bonds: the nitrile-silver(I) interaction using dicyanobithiophene as ligand

Reactions of the ligand 5,5′-dicyano-2,2′-bithiophene (T2CN2) with a variety of silver(I) salts are presented. In most cases, the ligand precipitates by itself without incorporating the silver(I) metal. However, when the counterion is triflate, in benzene or THF, a coordination compound is formed. The crystal structure of the species grown from benzene, a double-stranded one-dimensional polymer, is reported. In this structure, the bithiophene ligand is twisted into the uncommon syn orientation. The reasons for the lack of reactivity of the ligand are discussed by comparing the relative strengths of the interligand hydrogen bond with the ligand–metal bond.

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