Chiral discrimination in diastereomeric salts of chlorine-substituted mandelic acid and phenylethylamine

Chirality. 2010 Aug;22(8):707-16. doi: 10.1002/chir.20822.

Abstract

The crystal structures of diastereomeric salts of chloromandelic acid and phenylethylamine were determined and are presented herein. The structure comparison between less soluble salts and more soluble salts shows that weak interactions such as CH/pi interactions and van der Waals gain importance and contribute to chiral recognition when the hydrogen bonding patterns are very similar.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chlorine / chemistry*
  • Crystallography, X-Ray
  • Mandelic Acids / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Phenethylamines / chemistry*
  • Salts / chemistry*
  • Solubility
  • Stereoisomerism

Substances

  • Mandelic Acids
  • Phenethylamines
  • Salts
  • Chlorine
  • mandelic acid