Effenberger, FranzFischer, PeterSchöller, Wolfgang W.Stohrer, Wolf-Dieter2009-07-032016-03-312009-07-032016-03-311978311421296http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-42345http://elib.uni-stuttgart.de/handle/11682/970http://dx.doi.org/10.18419/opus-953From 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.eninfo:eu-repo/semantics/openAccessAnilin , Alkylamine540article2013-06-12