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Synthesis, spectral characterization, and structural investigation of mononuclear salen-type Cu(II) and Zn(II) complexes of a potentially octadentate N2O6 Schiff base ligand derived from binaphthol

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Abstract

A new potentially octadentate N2O6 Schiff base ligand, H2L derived from the condensation of 2,2′-(1,1′-binaphthyl-2,2′-diylbis(oxy))dianiline and o-vanillin, along with its copper(II) and zinc(II) complexes, is synthesized and has been characterized by elemental analyses, IR, UV–vis, 1H and 13C NMR spectra, as well as conductivity measurements. H2L forms mononuclear complexes of 1:1 (metal:ligand) stoichiometry with Cu(II) and Zn(II), and conductivity data confirm the non-electrolyte nature of these complexes. The [ZnL] and [CuL] complexes display very different solid-state structures, as determined by X-ray crystallography. While the [ZnL] complex has a distorted octahedral geometry about the metal, the [CuL] complex displays a distorted square planar geometry about the copper, with long Cu–O(ether) distances of 2.667 Å.

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Notes

  1. Cu–O bonds to neutral phenol are, on average, significantly longer than those to deprotonated phenol. The respective average values in the CSD (Version 5.32, November (2010)) are 2.399 and 1.910 Å.

  2. There are 671 instances of Cu(II)–ether O bonds, with distances ranging from 1.932 to 2.885 Å (mean = 2.338 Å, UQ = 2.535 Å). CSD Version 5.33, November (2011).

  3. There are 743 instances of Zn(II)–ether O bonds, with distances ranging from 1.966 to 2.839 Å (mean = 2.232 Å, UQ = 2.426 Å). CSD Version 5.33, November (2011).

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Acknowledgments

We are grateful to the Faculty of chemistry of Bu-Ali Sina University, National Foundation of elites (BMN) and Ministry of science, Research & Technology of Iran, for financial support.

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Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran

    Hassan Keypour & Maryam Shayesteh

  2. Chemistry Department, Payame Noor University, Tehran, 19395-4697, Iran

    Reza Golbedaghi

  3. Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand

    Allan G. Blackman & Scott A. Cameron

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  1. Hassan Keypour
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  2. Maryam Shayesteh
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  3. Reza Golbedaghi
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Corresponding author

Correspondence to Hassan Keypour.

Electronic supplementary material

Below is the link to the electronic supplementary material.

11243_2013_9728_MOESM1_ESM.doc

CCDCs 865429 and 865430 contain the supplementary crystallographic data of [ZnL]·CH3CN and [CuL]·2CHCl3 complexes respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif. (DOC 63 kb)

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Keypour, H., Shayesteh, M., Golbedaghi, R. et al. Synthesis, spectral characterization, and structural investigation of mononuclear salen-type Cu(II) and Zn(II) complexes of a potentially octadentate N2O6 Schiff base ligand derived from binaphthol. Transition Met Chem 38, 611–616 (2013). https://doi.org/10.1007/s11243-013-9728-2

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  • DOI: https://doi.org/10.1007/s11243-013-9728-2

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