Polarization‐Enhanced Hydrogen Bonding in 1,8‐Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis
Yazarlar (6)
Flora Mammadova
Bilkent Üniversitesi, Türkiye
Bilkent Üniversitesi, Türkiye
Büşra Hamarat
Hacettepe Üniversitesi, Türkiye
Hacettepe Üniversitesi, Türkiye
Dilgam Ahmadli
Bilkent Üniversitesi, Türkiye
Bilkent Üniversitesi, Türkiye
Prof. Dr. Onur ŞAHİN Sinop Üniversitesi, Türkiye
Prof. Dr. Uğur Bozkaya Hacettepe Üniversitesi, Türkiye
Yunus E. Türkmen
Bilkent Üniversitesi, Türkiye
Bilkent Üniversitesi, Türkiye
| Makale Türü | Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale) | ||
| Dergi Adı | Chemistryselect (Q3) | ||
| Dergi ISSN | 2365-6549 Dergi Bilgileri (2020) | ||
| Dergi Tarandığı Indeksler | SCI-Expanded | ||
| Makale Dili | Türkçe | Basım Tarihi | 01-2020 |
| Kabul Tarihi | 30-10-2020 | Yayınlanma Tarihi | 13-11-2020 |
| Cilt / Sayı / Sayfa | 5 / 42 / 13387–13396 | DOI | 10.1002/slct.202002960 |
| Makale Linki | http://dx.doi.org/10.1002/slct.202002960 | ||
| UAK Araştırma Alanları |
Yoğun Madde Fiziği
|
||
| 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 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 … |
| Anahtar Kelimeler |
| 1,8-dihydroxynaphthalene | cooperative effects | hydrogen bonds | NMR titration | organocatalysis |
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| Web of Science | 8 |
| Scopus | 8 |
| Google Scholar | 9 |