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Syntheses of amide based anion receptors and investigation of their associations with anions and their molecular structures using proton NMR titration and DFT methods

Journal of Molecular Structure, ISSN: 0022-2860, Vol: 1061, Issue: 1, Page: 32-40
2014
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    Citations
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  • 10
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  • Citations
    3
    • Citation Indexes
      3
  • Captures
    10
  • Social Media
    1
    • Shares, Likes & Comments
      1
      • Facebook
        1

Article Description

The synthesized disubstituted isophthalamide and pyridine-2,6dicarboxamide derivatives of nine compounds were prepared. Their association constants with tetrabutylammonium fluoride (TBA·F), tetrabutylammonium chloride (TBA·Cl), tetrabutylammonium bromide (TBA·Br), tetrabutylammonium dihydrogenphosphate (TBA·H 2 PO 4 ), tetrabutylammonium hydrogensulphate (TBA·HSO 4 ) and tetrabutylammonium nitrate (TBA·NO 3 ) were obtained by 1 H NMR titration technique. The optimized structures of compounds 1 – 9 and their association with F −, Cl −, Br −, H2PO4-, HSO4- and NO3- were obtained using the B3LYP/6-31+G(d) method. The most favorable complex of compound 3 with Br − was found. The high association constants of complexes 1 – 6 with F − are expected. Associations of all receptors with anions are exothermic and spontaneous reactions. Thermodynamic properties of all associations obtained using B3LYP/6-31+G(d) method are reported.

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