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Double Aromaticity and Ring Currents in All‐Carbon Rings
Author(s) -
Fowler Patrick W.,
Mizoguchi Noriyuki,
Bean David E.,
Havenith Remco W. A.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900322
Subject(s) - ring (chemistry) , aromaticity , plane (geometry) , planar , current (fluid) , ring current , angular momentum , atomic physics , molecular physics , chemistry , physics , geometry , mathematics , classical mechanics , quantum mechanics , thermodynamics , computer science , organic chemistry , magnetic field , earth's magnetic field , computer graphics (images) , molecule
Double aromaticity of neutral, planar rings of carbon atoms is demonstrated through visualisation of the induced ring currents, mapped at the ipsocentric B3LYP/6‐31G(d)//B3LYP/6‐31G(d) level for species C 6 to C 30 , with onset of delocalised current in the in‐plane π system at C 10 /C 11 . Both in‐plane and conventional out‐of‐plane π systems have diatropic/paratropic current in accordance with the Hückel rule, with 4 m +2 occupation of the out‐of‐plane π system taking precedence, as predicted by simple nesting of Frost–Musulin diagrams. The current‐density maps show characteristic double‐doughnut and double‐track topographies for out‐of‐plane and in‐plane ring currents, respectively, both governed by a common framework of angular momentum rules.