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

Autori
Čakić Semenčić, Mojca ; Kodrin, Ivan ; Molčanov, Krešimir ; Kovačević, Monika ; Rapić, Vladimir

Izvornik
Heliyon (2405-8440) 8 (2022), 5; E09470, 9

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA