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      https://www.ias.ac.in/article/fulltext/jcsc/121/06/0989-1001

    • Keywords

       

      2-Hydroxy Schiff bases; hydrogen bonding and tautomerism; crystal structure; heteronuclear correlation techniques.

    • Abstract

       

      Salicyclaldimines (5-9) and naphthaldimines (10-13) derived from condensation reactions of N2O2 donor type bifunctional aminopodands (1-4), [(H2NPhO)2R, where R = CH2CH2, CH2CH2CH2 and CH2PhCH2], and hydrazine monohydrate with salicylaldehyde and 2-hydroxy-1-naphthaldehyde, respectively, have been prepared (scheme 1) and characterized by elemental analyses, UV-vis, FTIR, NMR and MS. NMR assignments were made using 1H, 13C NMR, DEPT and aided by 2D HETCOR and HMBC heteronuclear correlation techniques. The UV-vis spectra of the Schiff bases have been systematically studied in organic solvents of different polarity, acidic and basic media and found useful in understanding of tautomeric equilibria (phenol-imine, O-H…N and keto-amine, O…H-N forms) in this series. The molecular structure of 8 has been determined crystallographically, and observed that the compound is in the form of phenol-imine, defined by the strong intramolecular [O-H…N = $1 \cdots 72$(3), $1 \cdots 81$(2) Å] hydrogen bonds. Compound 8 crystallizes in the monoclinic space group $P2_1/a$ with $a = 8 \cdots 4675$(7), $b = 38 \cdots 448$(3), $c = 9 \cdots 3875$(7) Å, $\beta = 103 \cdots 0780$(10)°, $V = 2976 \cdots 9$(4) Å3, $Z = 4$ and $D_x = 1 \cdots 271$ Mg m-3, and contains acetonitrile molecule in the crystal lattice.

    • Author Affiliations

       

      Selen Bi̇lge1 Zeynel Kiliç1 Zeli̇ha Hayvali1 Tuncer Hökelek2 Serap Safran1

      1. Department of Chemistry, Faculty of Science, Ankara University, Tandoğan, Ankara 06100, Turkey
      2. Department of Physics, Hacettepe University, Beytepe, Ankara 06800, Turkey
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