Polarization-Enhanced Hydrogen Bonding in 1,8-Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis
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Tarih
2020
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Wiley-V C H Verlag Gmbh
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
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.
Açıklama
Anahtar Kelimeler
cooperative effects, 1, 8-dihydroxynaphthalene, hydrogen bonds, NMR titration, organocatalysis
Kaynak
Chemistryselect
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
5
Sayı
42
