Stepwise Hydration Reveals Conformational Switching in Chiral Prolinol.

ABSTRACT: Understanding the interactions of chiral molecules with water is crucial, given the central role that water plays in chemical and biological processes. We report the investigation of the amino alcohol prolinol, a widely used chiral catalyst and auxiliary in asymmetric synthesis, and its interactions with one to three water molecules by applying broadband rotational spectroscopy. Bare prolinol adopts two low-energy conformations stabilized by an intramolecular O-H···N hydrogen bond. Upon complexation with a single water molecule, four prolinol-H₂O isomers are identified, showing addition and insertion structures, where the original prolinol conformations are conserved. Notably, complexation with two and three water molecules induces prolinol to adopt its highest energy conformati

SUBMITTER: Loru D 

PROVIDER: S-EPMC12750993 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature