Synthesis and spectroscopic properties of rotamers in the series of 2-(fluoroaryl)-4-substituted pyrroles
| Autor: | Alexander F. Smol'yakov, Dmitry I. Zhilyaev, Ilya V. Efimov, Leonid G. Voskressensky, Maria D. Matveeva, Almira R. Miftyakhova, Oleg S. Eltsov, Giovanni Talarico |
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| Přispěvatelé: | Miftyakhova, A. R., Matveeva, M. D., Zhilyaev, D. I., Eltsov, O. S., Talarico, G., Smol'Yakov, A. F., Voskressensky, L. G., Efimov, I. V. |
| Rok vydání: | 2021 |
| Předmět: |
Aryl
Organic Chemistry Substituent Nuclear magnetic resonance spectroscopy Carbon-13 NMR Pyrrole Rotamers Biochemistry Inorganic Chemistry Isocyanide chemistry.chemical_compound Crystallography chemistry Intramolecular force Environmental Chemistry Physical and Theoretical Chemistry Enamine Enaminone Conformational isomerism Cycloaddition Heteronuclear single quantum coherence spectroscopy |
| Zdroj: | Journal of Fluorine Chemistry. 249:109863 |
| ISSN: | 0022-1139 |
| DOI: | 10.1016/j.jfluchem.2021.109863 |
| Popis: | A mild, simple and efficient method for the synthesis of ortho, meta and para-fluoroaryl substituted pyrroles was discovered. It was found by NMR spectroscopy, that ortho-fluoroaryl substituted pyrroles exist in the form of inhibited conformational isomers (rotamers). Intramolecular interaction of the hydrogen atom of the pyrrole ring and the fluorine atom in the ortho-position of the aryl substituent leads to the appearance of two sets of signals in the 1H and 13C NMR spectra. Based on the combination of 2D HMBC and HSQC NMR spectroscopy, as well as temperature dependent NMR experiments in DMSO and CDCl3 we conclude that the ratio of obtained rotamers is permanent and does not depend from the temperature. |
| Databáze: | OpenAIRE |
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