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Updated: May 13, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
(S)-(-)-1-Phenyl-ethanaminium hexa-noate
1BP Institute and Department of Chemistry, University of Cambridge, Cambridge CB3 0EZ, England.
Chiral salt formation was achieved by reacting (S)-(-)-1-phenyl-ethanamine with hexanoic acid. The resulting crystal structure features N-H⋯O hydrogen-bonded chains along the c-axis.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Chiral resolution is crucial for separating enantiomers.
- Amine-acid salt formation is a common method for chiral resolution.
- Understanding crystal packing is key to predicting material properties.
Purpose of the Study:
- To synthesize and characterize a novel chiral salt.
- To investigate the supramolecular structure of the salt.
- To explore the potential of this salt in chiral applications.
Main Methods:
- Reaction of (S)-(-)-1-phenyl-ethanamine with hexanoic acid.
- Single-crystal X-ray diffraction analysis.
- Analysis of hydrogen bonding interactions.
Main Results:
- Formation of a 1:1 stoichiometric salt, C8H12N(+)·C6H11O2(-).
- Determination of a chiral crystal structure.
- Identification of N-H⋯O hydrogen-bonded chains along the c-axis.
Conclusions:
- The synthesized salt exhibits a well-defined chiral structure.
- Hydrogen bonding plays a significant role in stabilizing the crystal lattice.
- This study provides insights into the crystallization behavior of chiral amine-acid systems.
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