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Polarization‐Enhanced Hydrogen Bonding in 1,8‐Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis
Author(s) -
Mammadova Flora,
Hamarat Büşra,
Ahmadli Dilgam,
Şahin Onur,
Bozkaya Uğur,
Türkmen Yunus E.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002960
Subject(s) - hydrogen bond , intramolecular force , chemistry , intermolecular force , catalysis , density functional theory , titration , computational chemistry , hydrogen , nuclear magnetic resonance spectroscopy , proton nmr , polarization (electrochemistry) , low barrier hydrogen bond , crystallography , molecule , stereochemistry , organic chemistry
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 31 P‐NMR titration studies, demonstrated stronger complexation of Ph 3 PO 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 β ‐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.