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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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{
  "@context": "https://schema.org/", 
  "@id": 6827, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Mammadova, Flora"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Hacettepe Univ, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Hamarat, Busra"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Bilkent Univ, Fac Sci, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Ahmadli, Dilgam"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Sinop Univ, Sci & Technol Res Applicat & Res Ctr, TR-57000 Sinop, Turkey", 
      "name": "Sahin, Onur"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Hacettepe Univ, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Bozkaya, Ugur"
    }, 
    {
      "@type": "Person", 
      "name": "Turkmen, Yunus E."
    }
  ], 
  "datePublished": "2020-01-01", 
  "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.", 
  "headline": "Polarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis", 
  "identifier": 6827, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "Polarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis", 
  "url": "https://aperta.ulakbim.gov.tr/record/6827"
}
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