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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

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Published on: April 27, 2017

Controlling the Guanidinium Cation Rotation by Cation-π Interactions.

Hannah Busch1,2, Lennart Günzel3, Ettore Bartalucci1,2,4

  • 1Institute of Technical and Macromolecular Chemistry, RWTH Aachen University, Aachen, Germany.

Angewandte Chemie (International Ed. in English)
|May 21, 2026
PubMed
Summary
This summary is machine-generated.

Researchers trapped guanidinium cations in a π-container, restricting their rotation. This work brings chemists closer to controlling molecular motion using host-guest interactions.

Keywords:
cation–π interactiondynamicsfast magic‐angle spinningguanidiniumsolid‐state NMR

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Area of Science:

  • Supramolecular Chemistry
  • Solid-State Chemistry
  • Molecular Dynamics

Background:

  • Guanidinium is crucial in biology and chemistry, participating in molecular recognition via noncovalent interactions.
  • Guanidinium cations in solids typically exhibit rapid rotation (picoseconds) around symmetry axes.

Purpose of the Study:

  • To investigate host-guest interactions and control guanidinium cation rotation.
  • To utilize a π-container to trap guanidinium cations via cation-π interactions.

Main Methods:

  • Employing a π-container (calixarene framework) to encapsulate guanidinium.
  • Utilizing X-ray crystallography and solid-state nuclear magnetic resonance (NMR) spectroscopy.
  • Conducting temperature-dependent NMR experiments, quantum-chemical calculations, and molecular dynamics (MD) simulations.

Main Results:

  • Successfully trapped guanidinium cations within the π-container.
  • Characterized host-guest interactions and restricted guanidinium cation rotation.
  • Observed ns-order correlation times for rotation about the C3-axis, a significant slowdown from ps-scale.

Conclusions:

  • The calixarene framework acts as a bearing, effectively trapping and controlling guanidinium cation rotation.
  • This study demonstrates a method for achieving controlled molecular motion, a long-sought goal in chemistry.