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Aromaticity of the doubly charged [8]circulenes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Department of Organic Chemistry, Bohdan Khmelnitsky National University, Ukraine.
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2016 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 18, no 13, 8980-8992 p.Article in journal (Refereed) PublishedText
Abstract [en]

Magnetically induced current densities and current pathways have been calculated for a series of fully annelated dicationic and dianionic tetraphenylenes, which are also named [8]circulenes. The gauge including magnetically induced current (GIMIC) method has been employed for calculating the current density susceptibilities. The aromatic character and current pathways are deduced from the calculated current density susceptibilities showing that the neutral [8]circulenes have two concentric pathways with aromatic and antiaromatic character, respectively. The inner octatetraene core (the hub) is found to sustain a paratropic (antiaromatic) ring current, whereas the ring current along the outer part of the macrocycle (the rim) is diatropic (aromatic). The neutral [8]circulenes can be considered nonaromatic, because the sum of the ring-current strengths of the hub and the rim almost vanishes. The aromatic character of the doubly charged [8]circulenes is completely different: the dianionic [8]circulenes and the OC-, CH-, CH2-, SiH-, GeH-, SiH2-, and GeH2-containing dicationic species sustain net diatropic ring currents i.e., they are aromatic, whereas the O-, S-, Se-, NH-, PH- and AsH-containing dicationic [8]circulenes are strongly antiaromatic. The present study also shows that GIMIC calculations on the [8]circulenes provide more accurate information about the aromatic character than that obtained using local indices such as nuclear-independent chemical shifts (NICSs) and H-1 NMR chemical shifts.

Place, publisher, year, edition, pages
2016. Vol. 18, no 13, 8980-8992 p.
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Physical Chemistry
URN: urn:nbn:se:kth:diva-185602DOI: 10.1039/c6cp00365fISI: 000373000100023PubMedID: 26964752ScopusID: 2-s2.0-84962129727OAI: diva2:924209

QC 20160428

Available from: 2016-04-28 Created: 2016-04-25 Last updated: 2016-04-28Bibliographically approved

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Baryshnikov, Gleb V.
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