Novel ferrocene imide derivatives: synthesis, conformational analysis and X-ray structure. Issue 5 (May 2022)

• Record Type: Journal Article
• Authors: Semenčić, Mojca Čakić; Kodrin, Ivan; Molčanov, Krešimir; Kovačević, Monika; Rapić, Vladimir
• Is Part Of: Heliyon. Volume 8:Issue 5(2022)
• Publication Date: 2022-05
• Subjects: Conformational analysis -- Crystal structure -- DFT study -- Ferrocene -- Foldamers -- Imide; Research -- Periodicals; Medical sciences -- Periodicals; Natural history -- Periodicals; Social sciences -- Periodicals; Earth sciences -- Periodicals; Physical sciences -- Periodicals; 507.2
• DOI: 10.1016/j.heliyon.2022.e09470
• Languages: English
• ISSNs: 2405-8440

Abstract

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. Graphical abstract: Image 1 Abstract : Conformational analysis, Crystal structure, DFT study, Ferrocene, Foldamers, imide.