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Metastable Macrocyclic Bis-Meisenheimer Adduct.

Simon Pascal1,2, Angélina Torres Ruiz1, Aerin E Baker3

  • 1Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), Aix Marseille Univ, CNRS UMR 7325, Campus de Luminy, case 913, Marseille cedex 09, 13288, France.

Angewandte Chemie (International Ed. in English)
|July 8, 2025
PubMed
Summary

Electron-deficient tetranitroazacalixarene captures cyanide reversibly, forming a unique metastable dianionic macrocycle. This chemical system regenerates the original molecule under mild conditions, showcasing dynamic out-of-equilibrium behavior.

Keywords:
Chemical fuelDissipative systemMacrocycleMeisenheimer complexNucleophilic aromatic substitution

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Chemical Crystallography

Background:

  • Calixarenes are macrocyclic compounds with diverse applications.
  • Meisenheimer complexes are anionic intermediates in nucleophilic aromatic substitution.
  • Metastability in chemical systems is rare and scientifically significant.

Purpose of the Study:

  • To investigate the reversible cyanide capture by an electron-deficient tetranitroazacalixarene.
  • To characterize the resulting dianionic macrocycle and its unique properties.
  • To explore the dynamic behavior and stabilization mechanisms of the adduct.

Main Methods:

  • Single-crystal X-ray diffraction for structural determination.
  • Nuclear Magnetic Resonance (NMR) spectroscopy for characterization.
  • Electronic absorption spectroscopy to study electronic properties.
  • Computational analyses to understand stabilization.

Main Results:

  • Formation of a novel class of metastable dianionic macrocycles containing two Meisenheimer units.
  • Demonstration of reversible cyanide capture and release, acting as a chemical fuel.
  • Identification of intramolecular hydrogen bonding as a key stabilization factor.
  • Tunable dynamic behavior influenced by concentration, counterion, solvent, and temperature.

Conclusions:

  • Tetranitroazacalixarene enables reversible cyanide capture, forming a stable Meisenheimer complex adduct.
  • Macrocyclic preorganization and non-covalent interactions are crucial for this reversible reactivity.
  • The system exhibits dynamic behavior akin to out-of-equilibrium assemblies, offering new possibilities in molecular design.