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Molecular modeling annual

, Volume 6, Issue 2, pp 119–125 | Cite as

Molecular Dynamics of a Schiff Base Tetramacrocycle Studied by NMR and MD Simulations

  • Andreas Grohmann
  • Harald Lanig
  • Walter Bauer
  • Stefan Schmidt
  • Frank W. Heinemann
FULL PAPER

Abstract

Schiff base condensation of the pentadentate tetrapodal amine 1 with 2,6-diformyl-4-methylphenol 2 leads in a [3 + 6] condensation to a previously not described macrocycle 3 which shows C3-symmetry. X-ray analysis shows a truncated cone shape for 3. At T ≥ 100°C, the 1H-ROESY/EXSY spectrum reveals pairwise exchange of corresponding sites, indicative of inversion of the whole molecule in an umbrella-like fashion. Molecular dynamics simulations support this hypothesis.

Keywords Macrocycle, Schiff base, NMR, chemical exchange, MD, proton template, ROESY, EXSY 

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Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Andreas Grohmann
    • 1
  • Harald Lanig
    • 2
  • Walter Bauer
    • 3
  • Stefan Schmidt
    • 1
  • Frank W. Heinemann
    • 1
  1. 1.Institute of Inorganic Chemistry, University of Erlangen-Nürnberg, Egerlandstrasse 1, D-91058 Erlangen, Germany. Fax: +49-9131-8527367; E-mail: grohmann@anorganik.chemie.uni-erlangen.deDE
  2. 2.Computer Chemistry Center, Institute of Organic Chemistry, Nägelsbachstrasse 25, D-91052 Erlangen, GermanyDE
  3. 3.Institute of Organic Chemistry, University of Erlangen-Nürnberg, Henkestrasse 42, D-91054 Erlangen, GermanyDE

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