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The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
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Stepwise Hydration Reveals Conformational Switching in Chiral Prolinol.

Donatella Loru1, Elena R Alonso2, Aran Insausti2

  • 1Department of Chemistry, King's College London, London SE1 1DB, U.K.

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|December 11, 2025
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Summary
This summary is machine-generated.

Water significantly alters the shape of chiral molecules like prolinol. Even a few water molecules can force prolinol into high-energy structures, impacting its use in chemical synthesis.

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Area of Science:

  • Physical Chemistry
  • Chemical Physics
  • Molecular Interactions

Background:

  • Water's role in chemical and biological processes necessitates understanding chiral molecule interactions.
  • Prolinol is a key chiral auxiliary in asymmetric synthesis, making its hydration behavior significant.

Purpose of the Study:

  • Investigate the interactions between the chiral amino alcohol prolinol and 1-3 water molecules.
  • Determine how water influences prolinol's conformation and hydrogen bonding in different hydration states.

Main Methods:

  • Broadband rotational spectroscopy was used to study prolinol-(H2O)n complexes (n=1-3).
  • Nuclear Magnetic Resonance (NMR) studies and molecular dynamics simulations were employed for bulk water analysis.

Main Results:

  • Bare prolinol exists in low-energy conformations with an O-H---N hydrogen bond.
  • One water molecule forms addition and insertion structures without altering prolinol's conformation.
  • Two or three water molecules induce prolinol to adopt high-energy conformations (N-H---O hydrogen bond), acting as a conformational switch.
  • In bulk water, prolinol exists as a flexible ensemble, lacking stable intramolecular hydrogen bonds and sampling conformations similar to the di- and tri-hydrated states.

Conclusions:

  • Stepwise hydration profoundly changes the conformational landscape of flexible chiral molecules like prolinol.
  • Water's ability to act as a conformational switch is demonstrated, with implications for solvation-induced processes.
  • Findings provide a basis for future research on solvation effects in chiral chemistry and biology.