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Related Experiment Videos

Conformational preferences and self-template macrocyclization of squaramide-based foldable modules.

M Carmen Rotger1, M Neus Piña, Antonio Frontera

  • 1Departament de Química, Universitat de les Illes Balears, 07122 Palma de Mallorca, Illes Balears, Spain.

The Journal of Organic Chemistry
|March 31, 2004
PubMed
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Secondary squaramides exhibit potential for molecular folding due to their low rotational barriers. This study demonstrates the formation of stable, folded conformers stabilized by intramolecular hydrogen bonding, even in ethanol solutions.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • Secondary squaramides possess significant potential as hydrogen bond donors and acceptors.
  • Both anti- and syn-squaramide rotamers are observable in chloroform via Nuclear Magnetic Resonance (NMR) spectroscopy.
  • The energy barrier for anti/syn interconversion is approximately 63 kJ mol(-1).

Purpose of the Study:

  • To investigate the folding of secondary squaramides driven by low rotational barriers.
  • To demonstrate the formation of folded conformers stabilized by intramolecular hydrogen bonding.
  • To assess the influence of solvent polarity on squaramide folding and stability.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy for rotamer observation and conformational analysis.

Related Experiment Videos

  • Complete band shape analysis to determine the energetic barrier for interconversion.
  • Molecular mechanics calculations to support the existence of folded conformers.
  • Macrocyclization reactions in ethanol to indirectly assess folding effectiveness.

    • Main Results:

    • Secondary squaramides can form folded minimal modules through intramolecular hydrogen bonding, creating a nine-membered ring.
    • These folded conformers are stable and observable in chloroform and chloroform-ethanol mixtures.
    • Folding is effective even in pure ethanol, as evidenced by high yields in macrocyclization reactions.

    Conclusions:

    • The low rotational barrier of secondary squaramides is crucial for designing foldable molecular modules.
    • Intramolecular hydrogen bonding effectively stabilizes folded squaramide conformers.
    • Squaramide folding is a robust phenomenon, occurring across various solvent polarities and supporting efficient macrocyclization.