Resolution of sertraline with (R)-mandelic acid: Chiral discrimination mechanism study

Quan He, Sohrab Rohani, Jesse Zhu, Hassan Gomaa

Research output: Journal PublicationArticlepeer-review

16 Citations (Scopus)

Abstract

The chiral discrimination mechanism in the resolution of sertraline with mandelic acid was investigated by examining the weak intermolecular interactions (such as hydrogen bond, CH/π, and van der Waals interactions) and molecular packing difference in crystal structures of the resulting diastereomeric salts. A new one-dimensional chain-like hydrogen-bonding network and unique supramolecular packing mode are disclosed. The investigation demonstrated that stable hydrogen-bonding pattern, herringbone-like arrangement of aromatic rings, and planar boundary surface in the hydrophobic region are the three most important structural characteristics expected in less soluble diastereomeric salts. The existence and magnitude of hydrogen bond, CH/π interaction, and van der Waals interaction related to three characteristic structures, determine the stability of diastereomeric salt. The hydrogen bond is not necessarily the dominant factor while the synergy and optimization of all weak intermolecular interactions attribute to the chiral recognition.

Original languageEnglish
Pages (from-to)119-128
Number of pages10
JournalChirality
Volume24
Issue number2
DOIs
Publication statusPublished - Feb 2012
Externally publishedYes

Keywords

  • CH/π interaction
  • Chiral discrimination
  • Chiral recognition
  • Crystal packing
  • Crystallization resolution
  • Diastereomeric salt
  • Hydrogen bond
  • Mandelic acid
  • Sertraline

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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