Zinc halide template effects on the construction of [1 + 1] flexible Schiff-base macrocyclic complexes having pendant-armed dialdehyde components

Two novel pendant-armed dialdehydes (1a and 1b) were prepared by a one-step reaction between 5-chloro-3-(chloromethyl)-2-hydroxybenzaldehyde/5-methyl-3-(chloromethyl)-2-hydroxybenzaldehyde and cyclohexylamine involving two nucleophilic substitutions, and they were used to react with 1,3-propanediami...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2014-06, Vol.43 (22), p.8486-8492
Main Authors: Chen, Hui-Qing, Zhang, Kun, Jin, Chao, Huang, Wei
Format: Article
Language:English
Subjects:
Alterations
Anions
Cations
Construction
Forming
Halides
Macrocyclic compounds
Spectra
Zinc
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Summary:Two novel pendant-armed dialdehydes (1a and 1b) were prepared by a one-step reaction between 5-chloro-3-(chloromethyl)-2-hydroxybenzaldehyde/5-methyl-3-(chloromethyl)-2-hydroxybenzaldehyde and cyclohexylamine involving two nucleophilic substitutions, and they were used to react with 1,3-propanediamine to prepare Schiff-base macrocyclic complexes in the presence of ZnX2 salts (X = Cl, Br, and I). As a result, five dinuclear (2a, 2b, 3b, 4a, and 4b) and one mononuclear (3a) [1 + 1] flexible macrocyclic Zn(II) complexes have been structurally and spectrally characterized. The zinc centers in three pairs of macrocyclic complexes have the common four-coordinate tetrahedral geometry with one or two coordinated halide ions, where the template Zn(II) cations and the auxiliary halide anions with different sizes and coordination abilities are believed to play important roles in forming the resulting macrocyclic complexes. In addition, subtle alterations of electron-withdrawing and electron-donating substituted groups (Cl versus CH3) in the macrocyclic backbone result in different (1)H NMR and UV-vis spectra.
ISSN:1477-9226
1477-9234
DOI:10.1039/c4dt00605d