Details

Autor(en) / Beteiligte

• Kleinpeter, Erich
• Koch, Andreas

Titel

Identification of mesomeric substructures by through-space NMR shieldings (TSNMRS). Trimethine cyanine/merocyanine-like or aromatic π-electron delocalization?

Ist Teil von

• Tetrahedron, 2017-07, Vol.73 (30), p.4265-4274

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2017

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The spatial magnetic properties, through-space NMR shieldings (TSNMRS), of amino-substituted heteroaromatic six-membered ring systems such as pyrylium/thiopyrylium analogues 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 quantify and visualize the existing aromaticity of the studied compounds. Due to strong conjugation of six-membered ring π-electrons and lone pairs of the exo-cyclic amino substituents (restricted rotation about partial C,N double bonds) the interplay of still aromatic and already dominating trimethine cyanine/merocyanine-like substructures can be estimated. [Display omitted]