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Polarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis

Mammadova, Flora; Hamarat, Busra; Ahmadli, Dilgam; Sahin, Onur; Bozkaya, Ugur; Turkmen, Yunus E.


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        "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
        "name": "Mammadova, Flora"
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      {
        "affiliation": "Hacettepe Univ, Dept Chem, TR-06800 Ankara, Turkey", 
        "name": "Hamarat, Busra"
      }, 
      {
        "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
        "name": "Ahmadli, Dilgam"
      }, 
      {
        "affiliation": "Sinop Univ, Sci & Technol Res Applicat & Res Ctr, TR-57000 Sinop, Turkey", 
        "name": "Sahin, Onur"
      }, 
      {
        "affiliation": "Hacettepe Univ, Dept Chem, TR-06800 Ankara, Turkey", 
        "name": "Bozkaya, Ugur"
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      {
        "name": "Turkmen, Yunus E."
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    "description": "In this article, the presence and effects of polarization-enhanced hydrogen bonding in 1,8-dihydroxynaphthalene (1,8-DHN) were investigated in detail through a series of experimental and computational studies. First, the conformation of 1,8-DHN, and its ability to make intra- and intermolecular hydrogen bonds were investigated in solid state by X-ray crystallography, in solution by NMR spectroscopy, and computationally by density functional theory. Second, equilibrium binding constants, which were determined by P-31-NMR titration studies, demonstrated stronger complexation of Ph3PO with 1,8-DHN compared to mono-naphthol derivatives 8-methoxy-1-naphthol and 1-naphthol. In the final section, 1,8-DHN was observed to be an effective catalyst for the Friedel-Crafts-type addition reaction of indoles to beta-nitrostyrenes, and a rationale for this catalytic activity was provided via computational studies. All the findings described in this work support the enhanced hydrogen bond donating ability of 1,8-DHN due to polarization caused by the six-membered intramolecular hydrogen bond present in its structure.", 
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