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

Abstract

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-acetylferrocenecarboxamide (4) is characterized by N−H⋯O hydrogen bonds forming centrosymmetric dimers, while the molecules of its homologue N-methylferrocenecarboxamide (5) are self-assembled by intermolecular N−H⋯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.

Keywords

• Conformational analysis
• Crystal structure
• DFT study
• Ferrocene
• Foldamers
• Imide