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Copper(II) template synthesis of a new N2S2-donor macrocycle incorporating a pendent pyridyl substituent

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Abstract

The synthesis of the new potentially pentadentate ligand, 2,2′-(2-methyl-2-(pyridin-2-yl)propane-1,3-diyl)bis(sulfanediyl)diethanamine (L 1), containing two thioether sulfurs, two –NH2 amines and a pyridyl nitrogen heteroatom is described. Reaction of L 1 with copper(II) chloride and addition of hexafluorophosphate anion has led to isolation of the mixed anion complex Cu2(L 1)2Cl(PF6)3. The synthesis and X-ray structure of cobalt(III) species, [Co(L 1)Cl](PF6)2, is also reported. In situ reaction of L 1 with copper(II) as a metal template in the presence of formaldehyde and the carbon acid nitroethane together with triethylamine (as base) led to macrocycle ring closure to yield [Cu(L 2)Cl]PF6 (where L 2 = 6,13-dimethyl-6-nitro-13-(pyridin-2-yl)-1,11-dithia-4,8-diazacyclotetradecane) whose X-ray structure shows that the copper centre has a distorted square pyramidal coordination geometry being bound by both –NH2 nitrogens and both sulfurs of L 2 while the pyridyl nitrogen remains uncoordinated.

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Acknowledgments

We thank the National Research Foundation of Korea (2010-0016624) (YK) and the Australian Research Council (LFL and JKC) for support.

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Authors and Affiliations

  1. Department of Chemistry and Advanced Materials, Kosin University, 149-1, Dongsam-dong, Yeongdo-gu, Busan, 606-701, South Korea

    Cindy Mora, Young Hoon Lee & Yang Kim

  2. School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia

    Jack K. Clegg & Leonard F. Lindoy

  3. Department of Chemistry, Kyungpook National University, Daegu, 702-701, South Korea

    Hong In Lee

  4. Department of Applied Chemistry, Andong National University, Kyungpook, South Korea

    Woo Taik Lim

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  1. Cindy Mora
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  2. Young Hoon Lee
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  3. Jack K. Clegg
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  4. Leonard F. Lindoy
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  5. Hong In Lee
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  7. Yang Kim
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Correspondence to Yang Kim.

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Mora, C., Lee, Y.H., Clegg, J.K. et al. Copper(II) template synthesis of a new N2S2-donor macrocycle incorporating a pendent pyridyl substituent. J Incl Phenom Macrocycl Chem 71, 389–394 (2011). https://doi.org/10.1007/s10847-010-9886-1

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  • DOI: https://doi.org/10.1007/s10847-010-9886-1

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