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