Molecular modeling annual

, Volume 6, Issue 2, pp 318–327 | Cite as

Modeling of Supramolecular Properties of Molecular Tweezers, Clips, and Bowls

  • Frank-Gerrit Klärner
  • Jens Panitzky
  • Dorin Preda
  • Lawrence T. Scott
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Abstract

The electrostatic potential surface (EPS) is calculated for molecular tweezers, clips, and bowls at different levels of theory (semiempirical AM1, ab initio HF/6-31G*, and density functional theory pBP/DN**). According to these calculations, the molecular electrostatic potential (MEP) on the concave side of the molecular tweezers and clips is suprisingly negative for hydrocarbons. This finding seems to be a general phenomenon in nonconjugated π-electron systems with concave-convex topology and it explains the receptor properties of the molecular tweezers and clips. Analogous calculations performed for the conjugated aromatic molecular bowls show different results. The DFT calculations predict that in these systems the more negative MEP lies on the concave side similar to the findings for the nonconjugated molecular tweezer- and clip-systems, whereas the AM1 calculation leads to the opposite result that the MEP is more negative on convex side of the bowl-systems.

Keywords Electrostatic potential surfaces, Quantum mechanical calculations (AM1, ab initio, DFT), Artificial receptors, Supramolecular chemistry 

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Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Frank-Gerrit Klärner
    • 1
  • Jens Panitzky
    • 1
  • Dorin Preda
    • 2
  • Lawrence T. Scott
    • 2
  1. 1.Institut für Organische Chemie, Universität Essen, D-45117 Essen, Germany. Tel: +49-201-1833081; Fax: +49-201-1834252. E-mail: Klaerner@ocl.orgchem.uni-essen.deDE
  2. 2.Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467-3860, USAUS

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