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

Date

2010-01-01

Author

Türker, Burhan Lemi
Bayar, Caglar Celik
Balaban, Alexandru T.

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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.

Subject Keywords

Organic Chemistry, Materials Chemistry, Polymers and Plastics

URI

https://hdl.handle.net/11511/56921

Journal

POLYCYCLIC AROMATIC COMPOUNDS

DOI

https://doi.org/10.1080/10406631003756005

Collections

Department of Chemistry, Article

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Citation Formats

B. L. Türker, C. C. Bayar, and A. T. Balaban, “A DFT Study on Push-Pull (Amino-Nitro) Fulminenes and Hexahelicenes,” POLYCYCLIC AROMATIC COMPOUNDS, pp. 91–111, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56921.