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Related Experiment Videos

A multiple hydrogen-bond scaffold based on dipyrimidin-2-ylamine.

S H Söntjens1, J T Meijer, H Kooijman

  • 1Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.

Organic Letters
|November 27, 2001
PubMed
Summary

This study presents an accessible multiple hydrogen-bond array. The research found that steric effects influence selective binding in solution, highlighting the array

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Hydrogen-bond arrays are fundamental to molecular recognition.
  • Dipyrimidin-2-ylamine derivatives offer versatile platforms for designing hydrogen-bonding motifs.
  • Understanding factors influencing self-assembly is crucial for designing functional supramolecular systems.

Purpose of the Study:

  • To synthesize and characterize an easily accessible multiple hydrogen-bond array based on dipyrimidin-2-ylamine.
  • To investigate the impact of intramolecular hydrogen bonds, tautomeric equilibria, and steric effects on the self-association behavior of these molecules.
  • To explore the persistence and binding selectivity of the hydrogen-bond array in solution.

Main Methods:

  • Synthesis of dipyrimidin-2-ylamine derivatives.

Related Experiment Videos

  • X-ray diffraction analysis to determine solid-state structure.
  • (1)H NMR titrations to study solution-phase association and binding selectivity.

    • Main Results:

    • An accessible multiple hydrogen-bond array was successfully synthesized.
    • X-ray diffraction confirmed an acceptor-donor-acceptor (ADA) hydrogen-bonding array in the solid state.
    • The ADA array was found to persist in solution, with selective binding observed for molecules featuring sterically nondemanding donor-acceptor-donor (DAD) arrays.

    Conclusions:

    • Dipyrimidin-2-ylamine serves as a robust scaffold for constructing multiple hydrogen-bond arrays.
    • Intramolecular hydrogen bonding, tautomerism, and steric factors significantly modulate self-association behavior.
    • The study demonstrates the potential for designing selective molecular recognition systems based on these hydrogen-bond arrays.