Schiff bases of gossypol : an NMR and DFT study
Copyright (c) 2005 John Wiley & Sons, Ltd
| Veröffentlicht in: | Magnetic resonance in chemistry : MRC. - 1985. - 43(2005), 4 vom: 15. Apr., Seite 302-8 |
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| Weitere Verfasser: | , |
| Format: | Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2005
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| Zugriff auf das übergeordnete Werk: | Magnetic resonance in chemistry : MRC |
| Schlagworte: | Journal Article Research Support, Non-U.S. Gov't Carbon Isotopes Protons Schiff Bases Deuterium AR09D82C7G Gossypol KAV15B369O |
| Zusammenfassung: | Copyright (c) 2005 John Wiley & Sons, Ltd Schiff bases of gossypol with benzylamine, methylamine, 4-aminoacetophenone and 4-fluoroaniline have been synthesized and characterized by NMR spectroscopy. All the Schiff bases of gossypol are in the enamine form according to (3)J(HC,NH) and (1)J(N,H) coupling constants. The spectra are basically unchanged by change of solvent (CD(2)Cl(2), THF-d(8) and CD(3)OD) and by variation of temperature. For the derivative of benzylamine, deuterium isotope effects on (13)C chemical shifts are determined. They support strongly the enamine form and serve as a reference for other tautomeric Schiff bases. Structures and NMR nuclear shieldings of model compounds (the second monomer is replaced by a 2-hydroxybenzene ring) have been calculated by density functional theory (DFT) methods. A good correlation is observed between calculated (13)C nuclear shieldings of the enamine form and observed (13)C chemical shifts |
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| Beschreibung: | Date Completed 17.06.2005 Date Revised 21.11.2013 published: Print Citation Status MEDLINE |
| ISSN: | 1097-458X |