Synthesis and structures of Acetylferrocene (cas 1271-55-2) thiosemicarbazones and their dimethylthallium(III) complexes, which have four- or five-membered chelate rings

Add time:08/17/2019    Source:sciencedirect.com

Five thiosemicarbazones HLn=Fc(Me)C(2)N(3)N(2)(H)C(1)(S)N(1)R1R2 (Fc=ferrocenyl) were prepared by condensing Acetylferrocene (cas 1271-55-2) with thiosemicarbazide or 4-substituted thiosemicarbazides: acetylferrocene thiosemicarbazone (HL1), acetylferrocene 1N-methylthiosemicarbazone (HL2), acetylferrocene 1N-phenylthiosemicarbazone (HL3), acetylferrocene 1N-ethylthiosemicarbazone (HL4) and acetylferrocene 1N-dimethylthiosemicarbazone (HL5). All were characterized by IR and 1H and 13C NMR spectroscopy, and the structures of HL3, HL4 and HL5 were elucidated by X-ray crystallography. Reaction of dimethylthallium hydroxide with HL1HL5 afforded complexes [TlMe2(Ln)]. X-ray studies of [TlMe2(L2)], [TlMe2(L3)(dmso)]·dmso, [TlMe2(L4)] and [TlMe2(L5)] showed them to vary considerably as regards the coordination mode of the ligand. (L2)− and (L4)− form four-membered chelate rings via N(2) and S, and in the (L2)− complex an additional weak Tl⋯S interaction increases the coordination number of the metal to five and links the molecules in chains. [TlMe2(L4)] is the first thiosemicarbazone complex of TlMe2 + to have a coordination number of only four. In [TlMe2(L3)(dmso)]·dmso the more usual N(3),S-chelating mode gives rise to a five-membered chelate ring and there is an additional weak bond with a dmso oxygen. (L5)− is also N(3),S-chelating, but in this case dimers are formed by sulfur bridges. The differences in coordination are reflected in the TlLn distances.

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