A DFT Study on Push-Pull (Amino-Nitro) Fulminenes and Hexahelicenes

TÜRKER B. L. , Bayar C. C. , Balaban A. T.

POLYCYCLIC AROMATIC COMPOUNDS, cilt.30, sa.2, ss.91-111, 2010 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 30 Konu: 2
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1080/10406631003756005
  • Sayfa Sayıları: ss.91-111


In order to investigate the steric and electronic effects of electron-donor (amino) and -acceptor (nitro) substituents on hexahelicene and fulminene (isomeric and isoarithmic compounds), sixteen different types of terminal-amino-nitro hexahelicenes (H1-H16) and fulminenes (F1-F16) have been designed and investigated theoretically by the DFT method at B3LYP/6-31G(d) level. Besides electronic and thermodynamic properties, aromaticities (via NICS(0) calculations) have also been discussed for the above sets of terminal-rings-substituted hexahelicenes and fulminenes having 16 isomers each. Steric hindrance, seen enhanced in Hn structures, affects the total energies and heat of formations. The quinonoid conjugation is a minor factor in determining the trends in ring aromaticity of the above structures.