F···HO intramolecular hydrogen bond as the main transmission mechanism for (1h)J(F,H(O)) coupling constant in 2'-fluoroflavonol
Copyright © 2012 John Wiley & Sons, Ltd.
| Veröffentlicht in: | Magnetic resonance in chemistry : MRC. - 1985. - 50(2012), 8 vom: 01. Aug., Seite 551-6 |
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| Weitere Verfasser: | , |
| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2012
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| Zugriff auf das übergeordnete Werk: | Magnetic resonance in chemistry : MRC |
| Schlagworte: | Journal Article Research Support, Non-U.S. Gov't 2'-fluoroflavonol Flavonols Hydroxides Fluorine 284SYP0193 hydroxide ion 9159UV381P |
| Zusammenfassung: | Copyright © 2012 John Wiley & Sons, Ltd. Flavonoids are useful compounds in medicinal chemistry and exhibit conformational isomerism, which is ruled by intramolecular interactions. One of the main intramolecular forces governing the stability of conformations is the hydrogen bond. Hydrogen bond involving fluorine covalently bonded to carbon has been found to be rare, but it appears in 2'-fluoroflavonol, although the F···HO hydrogen bond cannot be considered the main effect governing the conformational stability of this compound. Because (19)F is magnetically active and suitable for NMR studies, the (1h)J(F,H(O)) coupling constant can be used as a probe for such an interaction in 2'-fluoroflavonol. In fact, the (1h)J(F,H(O)) coupling was computationally analyzed in this work, and the F···HO hydrogen bond was found to be its main transmission mechanism, which modulates this coupling in 2'-fluoroflavonol, rather than overlap of proximate electronic clouds, such as in 2-fluorophenol |
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| Beschreibung: | Date Completed 01.04.2013 Date Revised 21.11.2013 published: Print-Electronic Citation Status MEDLINE |
| ISSN: | 1097-458X |
| DOI: | 10.1002/mrc.3837 |