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

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dc.authoridTurkmen, Yunus/0000-0002-9797-2820
dc.authoridAhmadli, Dilgam/0000-0002-7720-8171
dc.contributor.authorMammadova, Flora
dc.contributor.authorHamarat, Busra
dc.contributor.authorAhmadli, Dilgam
dc.contributor.authorSahin, Onur
dc.contributor.authorBozkaya, Ugur
dc.contributor.authorTurkmen, Yunus E.
dc.date.accessioned2025-03-23T19:47:06Z
dc.date.available2025-03-23T19:47:06Z
dc.date.issued2020
dc.departmentSinop Üniversitesi
dc.description.abstractIn 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.
dc.description.sponsorshipBAGEP Award of the Science Academy, Turkey; Scientific and Technological Research Council of Turkey (TUBTAK) [116Z506]
dc.description.sponsorshipY.E.T. acknowledges the BAGEP Award of the Science Academy, Turkey. Financial support from the Scientific and Technological Research Council of Turkey (TUBTAK; Grant No: 116Z506) is gratefully acknowledged. We also acknowledge Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
dc.identifier.doi10.1002/slct.202002960
dc.identifier.endpage13396
dc.identifier.issn2365-6549
dc.identifier.issue42
dc.identifier.scopus2-s2.0-85096044178
dc.identifier.scopusqualityQ3
dc.identifier.startpage13387
dc.identifier.urihttps://doi.org/10.1002/slct.202002960
dc.identifier.urihttps://hdl.handle.net/11486/7281
dc.identifier.volume5
dc.identifier.wosWOS:000591276200056
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbh
dc.relation.ispartofChemistryselect
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectcooperative effects
dc.subject1
dc.subject8-dihydroxynaphthalene
dc.subjecthydrogen bonds
dc.subjectNMR titration
dc.subjectorganocatalysis
dc.titlePolarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis
dc.typeArticle

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