engleski

Novel ferrocene imide derivatives: synthesis, conformational analysis and X-ray structure

The synthesis and structural characterization of the ferrocene imide derivatives Fc-CO-NH-CO-Me (4), Fc-CO-NH-CO-Fc (7) and Fc-CO-NH-CO-Fn-CO-NH- CO-Fc (8) have been reported. The mononuclear, dinuclear and trinuclear ferrocene imides were prepared by the reaction of ferrocenecarboxamide (3), with acetyl chloride, ferrocenecarbonyl chloride (2) and ferrocene-1, 1’-(dicarbonyl chloride) (6), respectively. IR spectroscopic analysis revealed the absence of intramolecular hydrogen bonds in solutions of imides 4, 7 and 8. The crystal packing of N-acetylferrocene carboxamide (4) is characterized by NH⋯O hydrogen bonds forming centrosymmetric dimers, while the molecules of its homologue N-methylferrocene carboxamide (5) are self-assembled by intermolecular NH⋯O bonds into infinite chains. A detailed conformational analysis (DFT study) suggests the cis-trans configuration of ferrocene imide derivative 7 in solution. The effect of different substituents attached to bridged imide nitrogen on conformational properties of bis- ferrocenyl imides was further investigated and results compared to the existing experimental data.

conformational analysis ; crystal structure ; DFT study ; ferrocene foldamer ; imide

nije evidentirano