Polarization‐enhanced hydrogen bonding in 1,8‐dihydroxynaphthalene: conformational analysis, binding studies and hydrogen bonding catalysis

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buir.contributor.authorMammadova, Flora
buir.contributor.authorAhmadli, Dilgam
buir.contributor.authorTürkmen, Yunus Emre
dc.citation.epage13396en_US
dc.citation.issueNumber42en_US
dc.citation.spage13387en_US
dc.citation.volumeNumber5en_US
dc.contributor.authorMammadova, Flora
dc.contributor.authorHamarat, B.
dc.contributor.authorAhmadli, Dilgam
dc.contributor.authorŞahin, O.
dc.contributor.authorBozkaya, U.
dc.contributor.authorTürkmen, Yunus Emre
dc.date.accessioned2021-02-28T15:52:54Z
dc.date.available2021-02-28T15:52:54Z
dc.date.issued2020-11-16
dc.departmentDepartment of Chemistryen_US
dc.departmentInstitute of Materials Science and Nanotechnology (UNAM)en_US
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 31P‐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 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.en_US
dc.embargo.release2021-11-16
dc.identifier.doi10.1002/slct.202002960en_US
dc.identifier.issn2365-6549
dc.identifier.urihttp://hdl.handle.net/11693/75642
dc.language.isoEnglishen_US
dc.publisherWileyen_US
dc.relation.isversionofhttps://dx.doi.org/10.1002/slct.202002960en_US
dc.source.titleChemistrySelecten_US
dc.subjectCooperative effectsen_US
dc.subject1,8-dihydroxynaphthaleneen_US
dc.subjectHydrogen bondsen_US
dc.subjectNMR titrationen_US
dc.subjectOrganocatalysisen_US
dc.titlePolarization‐enhanced hydrogen bonding in 1,8‐dihydroxynaphthalene: conformational analysis, binding studies and hydrogen bonding catalysisen_US
dc.typeArticleen_US
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Institute of Materials Science and Nanotechnology (UNAM)