Synthesis and Electrochemical Properties of N-(Ferrocenylmethyl)Aminobenzonitrile and N-(Ferrocenylmethyl)Nitroaniline Derivatives

Abstract

Seven novel ferrocene derivatives containing (methylamino)benzonitrile and Nmethylnitroaniline groups (3a-3f and 4) have been synthesized by conventional methods and characterized by FT-IR, NMR and cyclic voltammetry. The electrochemical behavior of these compounds (3a-3f) has been studied by cyclic voltammetry measurements at a platinum electrode in acetonitrile/0.1 M TBAP. The ferrocenyl group in all compounds showed similar reversible oneelectron redox process, suggesting that the ferrocene moieties are equivalent and that there are no interactions among them. The formal potential, , is shifted to the more positive potential, indicating that the (methylamino)benzonitrile and N-methylnitroaniline introduced to ferrocene moiety exercise an electron-withdrawing effect.

A Molecular Docking Study of N-Ferrocenylmethylnitroanilines as Potential Anticancer Drugs

“…In our previous research, we have described the synthetic routes and full characterisation of compounds 2a, 2b and 2c as illustrated in Scheme 1 [22,23]. Scheme 1.…”

Determination of binding parameters of 2-(Ferrocenylmethylamino) Benzonitrile and 3-(Ferrocenylmethylamino)Benzonitrile WITH 1,1-Diphenyl-2-Picrylhydrazyl free radical

“…2-(ferrocenylmethylamino)benzonitrile and 3-(ferrocenylmethylamino)benzonitrile were synthesized as described previously [9] cleanly and in high yield from the reaction of the well-known quaternary salt ferrocenylmethyltrimethylammonium iodide [10] (1) and 2-and 3-aminobenzonitrile respectively, scheme 1. All compounds gave analytical and spectroscopic data in accordance with the proposed structures.…”

Experimental partition determination of octanol-water coefficients of ferrocene derivatives using square wave voltammetry techniques

“…N-ferrocenylmethylaniline [12], ferrocenyl-2-nitrophenyl [13], N-ferrocenymethyl-N-phenylpropionamide [14], N'-ferrocenylmethyl-N'-phenylbenzohydrazide [15], ferrocenyl-4-nitrophenyl [16], Nferrocenymethyl-N-phenylacetamide [17], 1-ferrocenylethanol [18], N-Ferrocénylmethyl(2-cyano) aniline [19], 4-(ferrocenylmethylamino)benzonitrile [19] were all obtained according to literature procedures.…”