Mammadova, FloraHamarat, BusraAhmadli, DilgamSahin, OnurBozkaya, UgurTurkmen, Yunus E.2025-03-232025-03-2320202365-6549https://doi.org/10.1002/slct.202002960https://hdl.handle.net/11486/7281In 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.eninfo:eu-repo/semantics/closedAccesscooperative effects18-dihydroxynaphthalenehydrogen bondsNMR titrationorganocatalysisArticle542133871339610.1002/slct.2020029602-s2.0-85096044178Q3WOS:000591276200056Q3