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Molecular modeling annual

, Volume 6, Issue 2, pp 226–233 | Cite as

The Interplay of Angle Strain and Aromaticity: Molecular and Electronic Structures of [0n]Paracyclophanes

  • Mavinahalli N. Jagadeesh
  • Anindita Makur
  • Jayaraman Chandrasekhar
FULL PAPER

Abstract

The belt-like polyphenylenes, [0n]paracyclophanes, (n = 5 and 6), have been investigated using semi-empirical, ab initio and DFT methods. The molecular structure, rotational barrier on twisting a single phenyl ring and the aromatic character within each ring as well as in the whole molecule have been evaluated. [05]Paracyclophane is predicted to have a quinonoid structure. In contrast, the equatorial pentaphenyl fragment found in C70 as well as the hexagons of the less strained [06]paracyclophane have benzenoid character. Approximate band structures have been derived for larger cycles of [0n] paracyclophanes.

Keywords Strained rings, Aromaticity, Ab initio, AM1, MNDO, B3LYP 

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Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Mavinahalli N. Jagadeesh
    • 1
  • Anindita Makur
    • 2
  • Jayaraman Chandrasekhar
    • 1
  1. 1.Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. Tel.: 91-80-3092578; Fax: 91-80-360 0529. E-mail: chandru@master.chem.yale.eduIN
  2. 2.Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur P.O., Bangalore 560064, IndiaIN

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