Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

  • Gleb V. Baryshnikov
  • Boris F. Minaev
  • Pittelkow, Michael
  • Christian Benedikt Nielsen
  • Roberto Salcedo
Recently synthesized p-extended symmetrical tetraoxa[8]circulenes that exhibit electroluminescent properties were calculated at the density functional theory (DFT) level using the quantum theory of atoms in molecules (QTAIM) approach to electron density distribution analysis. Nucleus-independent chemical shift (NICS) indices were used to characterize the aromaticity of the studied molecules. The tetraoxa[8]circulene molecules were found to consist of two antiaromatic perimeters (according to the Hückel "4n" antiaromaticity rule) that include 8 and 24 p-electrons. Conversely, NICS calculations demonstrated the existence of a common p-extended system (distributed like a flat ribbon) in the studied tetraoxa[8]circulene molecules. Thus, these symmetrical tetraoxa[8]circulene molecules provide examples of diatropic systems characterized by the presence of induced diatropic ring currents.
OriginalsprogEngelsk
TidsskriftJournal of Molecular Modeling
Vol/bind19
Udgave nummer2
Sider (fra-til)847-850
Antal sider4
ISSN1610-2940
DOI
StatusUdgivet - 2013

ID: 45649645