A nitrogen-15 NMR study of hydrogen bonding in 1-alkyl-4-imino-1,4-dihydro-3-quinolinecarboxylic acids and related compounds
Copyright 2006 John Wiley & Sons, Ltd.
| Veröffentlicht in: | Magnetic resonance in chemistry : MRC. - 1985. - 44(2006), 5 vom: 15. Mai, Seite 510-4 |
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| Weitere Verfasser: | , |
| Format: | Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2006
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| Zugriff auf das übergeordnete Werk: | Magnetic resonance in chemistry : MRC |
| Schlagworte: | Journal Article Research Support, Non-U.S. Gov't Carboxylic Acids Nitrogen Isotopes Quinolines quinoline E66400VT9R |
| Zusammenfassung: | Copyright 2006 John Wiley & Sons, Ltd. The title compounds contain groups (amine, amide, imine, carboxylic acid) that are capable of forming intramolecular hydrogen bonds involving a six-membered ring. In compounds where the two interacting functional groups are imine and carboxylic acid, the imine is protonated to give a zwitterion; where the two groups are imine and amide, the amide remains intact and forms a hydrogen bond to the imine nitrogen. The former is confirmed by the iminium 15N signal, which shows the coupling of 1J(15N,1H) -85 to -86.8 Hz and 3J(1H,1H) 3.7-4.2 Hz between the iminium proton and the methine proton of a cyclopropyl substituent on the iminium nitrogen. Hydrogen bonding of the amide is confirmed by its high 1H chemical shift and by coupling of the amide hydrogen to (amide) nitrogen [(1J(15N,1H) -84.7 to -90.7 Hz)] and to ortho carbons of a phenyl substituent. Data obtained from N,N-dimethylanthranilic acid show 15N-1H coupling of (-)8.2 Hz at 223 K (increasing to (-)5.3 Hz at 243 K) consistent with the presence of a N... H-O hydrogen bond |
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| Beschreibung: | Date Completed 17.08.2007 Date Revised 15.11.2012 published: Print Citation Status MEDLINE |
| ISSN: | 1097-458X |