Paramagnetic ring current effects in anti-aromatic structures subject to substitution/annelation quantified by spatial magnetic properties (TSNMRS)

The spatial magnetic properties, through-space NMR shieldings (TSNMRS), of the typically anti-aromatic cyclopentadienyl cation, cyclobutadiene, pentalene, s-indacene and of substituted/annelated analogues of the latter structures have been calculated using the GIAO perturbation method employing the...

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Bibliographic Details
Published inTetrahedron Vol. 74; no. 7; pp. 700 - 710
Main Authors Kleinpeter, Erich, Koch, Andreas
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 15.02.2018
Subjects
Annelation effect
Anti-aromaticity
Aromaticity
GIAO
NICS
Through-space NMR shieldings (TSNMRS)
GIAO
Anti-aromaticity
Through-space NMR shieldings (TSNMRS)
Aromaticity
Annelation effect
NICS
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Summary:The spatial magnetic properties, through-space NMR shieldings (TSNMRS), of the typically anti-aromatic cyclopentadienyl cation, cyclobutadiene, pentalene, s-indacene and of substituted/annelated analogues of the latter structures have been calculated using the GIAO perturbation method employing the nucleus independent chemical shift (NICS) concept and visualized as iso-chemical-shielding surfaces (ICSS) of various size and direction. The TSNMRS values were employed to visualize and quantify the dia(para)magnetic ring current effects in the studied compounds. The interplay of dia(para)magnetic ring current effects due to substitution/annelation caused by heavy exo-cyclic n,π-electron delocalization can be qualified. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.12.020