New 1,2-disubstituted ferrocenyl stibines containing N-heterocyclic pendant arm: Sb–N hypervalent compounds

New 1,2-disubstituted ferrocenyl stibines viz. containing -CH2NR or -CH2NHR pendant arm at the ortho-position have been synthesized and characterized by various physicochemical methods. These new ferrocenylstibines were prepared by the nucleophilic substitution reaction of diphenyl[(N,N,N-trimethylaminomethylferrocenyl)iodide]stibine by different primary amines and secondary heterocyclic amines viz. furan-2-ylmethylamine, p-aminoacetophenone, 3-(1-hydroxyethyl)-aniline, 4-hydroxypiperidine, 1-ethylpiperazine and 4-(4-bromophenyl)-4-hydroxypiperidine. Molecular structure of stibine (2), (3), (5) and (7) have been determined by X-ray crystallography. Stibine (2), (5) and (7) show a weak hypervalent Sb–N interaction while stibine (3) does not show this interaction in solid state.

Graphical abstractNew 1,2-disubstituted ferrocenyl stibines viz. containing -CH2NR or -CH2NHR pendant arm at the ortho-position have been synthesized and characterized by various physicochemical methods. These new ferrocenylstibines were prepared by the nucleophilic substitution reaction of diphenyl[(N,N,N-trimethylaminomethylferrocenyl)iodide]stibine by different primary amines and secondary heterocyclic amines viz. furan-2-1-ylmethylamine, p-aminoacetophenone, 3-(1-hydroxyethyl)-aniline, 4-hydroxypiperidine, 1-ethylpiperazine and 4-(4-bromophenyl)-4-hydroxypiperidine. Molecular structure of stibine (2), (3), (5) and (7) have been determined by X-ray crystallography. Stibine (2), (5) and (7) show a weak hypervalent Sb–N interaction while stibine (3) does not show this interaction in solid state.Figure optionsDownload full-size imageDownload as PowerPoint slide