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Efficient synthesis and metal cations complexation of some novel dinaphthosulfide-substituted macrocyclic diamides

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Abstract

Some dinaphthosulfide aza macrocycles (3–9) were synthesized based on the conventional route from the reaction of corresponding dinaphthosulfide diester and aliphathic diamines in refluxing methanol in good yields. Dinaphthosulfide diester were synthesized from the reaction of 1,1′-thiobis (2-hydroxy naphthalene) and methyl chloroacetate. The structures of these compounds were confirmed using IR, 1H NMR, 13C NMR, MASS spectroscopy and elemental analysis. Conductometric studies of the complexation of some metal ions with aza derivative 8 (TDN) in methanol as solvent implied the formation of 1:1 complexes. The stability of the 1:1 complexes of TDN decreases in the order Hg2+ >> Pb2+ > Cu2+ > Zn2+ > Ca2+ > Mg2+ > Cd2+ > Sr2+ > Ag+ > Ba2+.

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Authors and Affiliations

  1. Faculty of Chemistry, Tarbiat Moallem University, Mofatteh Ave., no. 49, 15614, Tehran, Iran

    Abbas Shockravi, Hanif Fattahi, Mehdi Taghdiri, Davood Heidaryan, Esmael Rostami, Mehdi Abbaszadeh & Ali Yousefi

  2. Department of Chemistry, Razi University, Kermanshah, Iran

    Mojtaba Shamsipur

  3. Department of Chemistry, Lorestan University, Khorram, Abad, Iran

    Kamal Alizadeh

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  1. Abbas Shockravi
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  2. Mojtaba Shamsipur
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  3. Hanif Fattahi
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Correspondence to Abbas Shockravi.

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Shockravi, A., Shamsipur, M., Fattahi, H. et al. Efficient synthesis and metal cations complexation of some novel dinaphthosulfide-substituted macrocyclic diamides. J Incl Phenom Macrocycl Chem 61, 153–160 (2008). https://doi.org/10.1007/s10847-008-9408-6

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  • DOI: https://doi.org/10.1007/s10847-008-9408-6

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