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Efficient synthesis and metal cations complexation of some novel dinaphthosulfide-substituted macrocyclic diamides
Authors:Abbas Shockravi  Mojtaba Shamsipur  Hanif Fattahi  Mehdi Taghdiri  Davood Heidaryan  Kamal Alizadeh  Esmael Rostami  Mehdi Abbaszadeh  Ali Yousefi
Affiliation:1. Faculty of Chemistry, Tarbiat Moallem University, Mofatteh Ave., no. 49, 15614, Tehran, Iran
2. Department of Chemistry, Razi University, Kermanshah, Iran
3. Department of Chemistry, Lorestan University, Khorram, Abad, Iran
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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