Synthesis, characterization and crystal structures of a new 2-ferrocenylnaphthoxazole and its mercurated derivatives

A new ferrocenylnaphthoxazole [(η5-C5H5)Fe{(η5-C5H4)C(O)N(C10H6)}] (1) was synthesized under mild conditions. Two mercurated derivatives: ortho-mercurated product [HgCl{(η5-C5H5)Fe[(η5-C5H3)C(O)N(C10H6)]}] (2) and the product mercurated on the unsubstituted Cp ring [HgCl{(η5-C5H4)Fe[(η5-C5H4)C(O)N(C10H6)]}] (3) were obtained by the reaction of 1 with mercuric acetate. All the new compounds 1, 2 and 3 were characterized by elemental analyses, IR, NMR, MS spectra and X-ray crystal structure analysis. The crystal structure of 1 extended into a 2D supramolecular network through the intermolecular π–π stacking interaction between the Cp ring and naphthoxazole ring. In the crystal of 2, there exist bridged Cl–Hg bonds, CH(Cp) ⋯ Cl and CH⋯ Hg hydrogen bonds, π–π stacking interactions, which facilitate construction of this complex into a 3D supramolecular structure.

Graphical abstractA new ferrocenylnaphthoxazole [(η5-C5H5)Fe{(η5-C5H4)–C(O)N(C10H6)}] (1) and its mercurated derivatives [HgCl{(η5–C5H5)Fe[(η5–C5H3)C(O)N(C10H6)]}] (2) and [HgCl{(η5–C5H4)Fe[(η5–C5H4)C(O)N(C10H6)]}] (3) were synthesized. The crystal structure of 1 was stabilized by the intermolecular π–π stacking interaction between the Cp ring and naphthoxazole ring. In the crystal of 2, there exist bridged Cl–Hg bonds, CH(Cp) ⋯ Cl and CH ⋯ Hg hydrogen bonds, π–π stacking interactions, which facilitate construction of this complex into a 3D supramolecular structure.Figure optionsDownload full-size imageDownload as PowerPoint slide