(Chemical Equation Presented) Traces of magnetizability, traces of magnetic shielding at the hydrogen nuclei, and nucleus-independent chemical shift are not reliable aromaticity quantifiers for planar conjugated hydrocarbons. A measure of aromaticity is provided by the out-of-plane tensor components, whose magnitude is influenced by the π-ring currents. The failure of nucleus-independent chemical shift in this regard was proved for the molecule shown in the abstract graphic, sustaining a diatropic π-current. The validity of the ring-current model is reaffirmed. © 2005 American Chemical Society.
Why downfield proton chemical shifts are not reliable aromaticity indicators / Faglioni, F.; Ligabue, A.; Pelloni, S.; Soncini, A.; Viglione, R. G.; Ferraro, M. B.; Zanasi, R.; Lazzeretti, P.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 7:16(2005), pp. 3457-3460. [10.1021/ol051103v]
Why downfield proton chemical shifts are not reliable aromaticity indicators
Faglioni F.;Lazzeretti P.
2005
Abstract
(Chemical Equation Presented) Traces of magnetizability, traces of magnetic shielding at the hydrogen nuclei, and nucleus-independent chemical shift are not reliable aromaticity quantifiers for planar conjugated hydrocarbons. A measure of aromaticity is provided by the out-of-plane tensor components, whose magnitude is influenced by the π-ring currents. The failure of nucleus-independent chemical shift in this regard was proved for the molecule shown in the abstract graphic, sustaining a diatropic π-current. The validity of the ring-current model is reaffirmed. © 2005 American Chemical Society.
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