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http://dx.doi.org/10.18419/opus-953
Autor(en): | Effenberger, Franz Fischer, Peter Schöller, Wolfgang W. Stohrer, Wolf-Dieter |
Titel: | The donor strength of dialkylamino functions : a systematic study of delta H /HMO pi-electron density correlations in aminobenzenes |
Erscheinungsdatum: | 1978 |
Dokumentart: | Zeitschriftenartikel |
Erschienen in: | Tetrahedron 34 (1978), S. 2409-2417. URL http://dx.doi.org./10.1016/0040-4020(78)89060-7 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-42345 http://elib.uni-stuttgart.de/handle/11682/970 http://dx.doi.org/10.18419/opus-953 |
Zusammenfassung: | From the resonance interaction between different NR2 substituents and the arylic π-system in mono-,1, 3-bis- and 1,3,5-tris(dialkylamino)benzenes, quantitative parameters are derived for the relative donor strength of the pyrrolidino, dimethylamino, piperidino and morpholino group. Towards an uncharged π-system in the ground state, the donor potential decreases in the series Pyr>N(CH3)2>Pip>Mor. The same order, though with somewhat different gradation, is observed for the aminobenzene/trinitrobenzene charge transfer complex absorptions, and for the polarographic oxidation potentials. The detailed analysis of the chemical shift/π-charge density correlations for methoxy and dialkylamino benzenes also reveals that these substituents exert a significant deshielding effect on protons in ortho-position. This additional downfield shift is probably due to steric interactions and strongly increases from the pyrrolidino to the piperidino group. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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eff111.pdf | 740,71 kB | Adobe PDF | Öffnen/Anzeigen |
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