Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds
| Autor: | Craig D. Grimmer, Vuyisa Mzozoyana, Fanie R. van Heerden |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
fluorinated phenylcoumarin
Chemistry Intermolecular force Organic Chemistry f···h hydrogen bond Supramolecular chemistry chemistry.chemical_element Carbon-13 NMR Ring (chemistry) dft through-space coupling Full Research Paper lcsh:QD241-441 Crystallography lcsh:Organic chemistry pechmann reaction Intramolecular force Fluorine Proton NMR lcsh:Q lcsh:Science Single crystal |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 190-199 (2020) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | 4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (JFH = 2.6 Hz) and 13C NMR suggested that this C–F···H–C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C–F···H–C interaction. |
| Databáze: | OpenAIRE |
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