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Ring Currents in Benzo‐ and Benzocyclobutadieno‐Annelated Biphenylene Derivatives
Author(s) -
Radenković Slavko,
Tošović Jelena,
Havenith Remco W. A.,
Bultinck Patrick
Publication year - 2015
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201402468
Subject(s) - biphenylene , antiaromaticity , annulation , chemistry , ring (chemistry) , aromaticity , computational chemistry , stereochemistry , organic chemistry , phenylene , molecule , catalysis , polymer
The effect of benzo and benzocyclobutadieno annelation on the current density induced in a series of biphenylene derivatives is examined at the B3LYP/cc‐pVDZ level of theory, by using the CTOCD‐DZ method. Angular benzo annelation increases, whereas linear benzo annelation decreases the intensity of paratropic (antiaromatic) current density along the four‐membered ring of biphenylene. The opposite effect is found for benzocyclobutadieno annelation. It is shown that the extent of local aromaticity of the four‐membered ring in biphenylene congeners can vary from highly antiaromatic to nonaromatic, as a result of different modes of annelation.