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

Abstract

New 1,2-disubstituted ferrocenyl stibines viz. containing -CH 2 NR or -CH 2 NHR 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. New 1,2-disubstituted ferrocenyl stibines viz. containing -CH 2 NR or -CH 2 NHR 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.