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Crystal Structure Investigations on Imines derived from 3‐Ferrocenyl‐prop‐2‐enal Crystallizing in Non‐centrosymmetric Space Groups
Author(s) -
Imhof Wolfgang
Publication year - 2005
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200400371
Subject(s) - furan , chemistry , hydrogen bond , molecule , crystal structure , amine gas treating , cyclopentadienyl complex , aniline , diamine , crystallography , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The condensation of 3‐ferrocenyl‐prop‐2‐enal with primary amines leads to the formation of the corresponding imines in good yields. The crystal structures of imines derived from p ‐dimethylamino‐aniline and furfurylamine are determined by the ability of the functional groups to act as hydrogen bond donor or acceptor sites. Although N, N‐dimethyl‐N′‐(3‐ferrocenyl‐allylidene)‐benzene‐1, 4‐diamine and furan‐2‐ylmethyl‐(3‐ferrocenyl‐allylidene)‐amine are achiral molecules they crystallize in the non‐centrosymmetric space groups P2 1 and Pca2 1 , respectively. The molecular architecture of N, N‐dimethyl‐N′‐(3‐ferrocenyl‐allylidene)‐benzene‐1, 4‐diamine is realized by the incorporation of dichloromethane acting as hydrogen bond donor and acceptor with both hydrogen and both chlorine atoms. On the other hand, the molecules of furan‐2‐ylmethyl‐(3‐ferrocenyl‐allylidene)‐amine are linked by hydrogen bonds towards the centroid of one of the cyclopentadienyl ligands and towards the oxygen atom of the furan ring to produce infinite chains.