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Resolution of sertraline with (R) ‐mandelic acid: Chiral discrimination mechanism study
Author(s) -
He Quan,
Rohani Sohrab,
Zhu Jesse,
Gomaa Hassan
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21033
Subject(s) - chemistry , hydrogen bond , van der waals force , diastereomer , intermolecular force , supramolecular chemistry , non covalent interactions , molecular recognition , crystallography , computational chemistry , stereochemistry , crystal structure , molecule , organic chemistry
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 . Chirality, 2012. © 2011 Wiley Periodicals, Inc.