1 Ocak 2020 Dergi makalesi Açık Erişim

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

Citation Style Language JSON

{
  "DOI": "10.1002/slct.202002960", 
  "abstract": "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.", 
  "author": [
    {
      "family": "Mammadova", 
      "given": " Flora"
    }, 
    {
      "family": "Hamarat", 
      "given": " Busra"
    }, 
    {
      "family": "Ahmadli", 
      "given": " Dilgam"
    }, 
    {
      "family": "Sahin", 
      "given": " Onur"
    }, 
    {
      "family": "Bozkaya", 
      "given": " Ugur"
    }, 
    {
      "family": "Turkmen", 
      "given": " Yunus E."
    }
  ], 
  "container_title": "CHEMISTRYSELECT", 
  "id": "6827", 
  "issue": "42", 
  "issued": {
    "date-parts": [
      [
        2020, 
        1, 
        1
      ]
    ]
  }, 
  "page": "13387-13396", 
  "title": "Polarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis", 
  "type": "article-journal", 
  "volume": "5"
}