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Updated: Apr 18, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Crystal structure of (4S)-aminoproline: conformational insight into a pH-responsive proline derivative
Christiane Siebler1, Nils Trapp, Helma Wennemers
1Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, CH-8093, Zürich, Switzerland.
Abstract:
The crystal structure of a (4S)-configured ammoniumproline derivative is presented. The trifluoroacetic acid salt of the acetylated methylester of (4S)-aminoproline (Ac-(4S)Amp-OMe) crystallized as the trans conformer with a C(4)-endo ring pucker. The high-resolution structure shows typical parameters for a transannular H-bond and an n → π* interaction between the adjacent amide and ester groups. The structure corroborates previous findings of solution phase studies on the importance of these two interactions in acidic and neutral aqueous environments for the conformation of this pH-responsive proline derivative.
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