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Aromaticity and Antiaromaticity in Five‐Membered C 4 H 4 X Ring Systems: “Classical” and “Magnetic” Concepts May Not Be “Orthogonal”
Author(s) -
von Ragué Schleyer Paul,
Jiao Haijun,
Goldfuss Bernd,
Freeman Peter K.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199503371
Subject(s) - antiaromaticity , diamagnetism , aromaticity , ring (chemistry) , magnetic susceptibility , yield (engineering) , chemistry , paramagnetism , ring current , computational chemistry , crystallography , materials science , condensed matter physics , physics , magnetic field , molecule , organic chemistry , quantum mechanics , earth's magnetic field , metallurgy
Energetic, geometric, and magnetic criteria yield quantitatively the same order of aromaticity (antiaromaticity) for the five‐membered ring systems 1 : the aromatic 6π electron systems are stabilized, their bond lengths are equalized, and the magnetic susceptibility exaltations are diamagnetic. In contrast, the antiaromatic 4π electron systems are destabilized, double bonds are localized, and susceptibility exaltations are paramagnetic.