Chiral discrimination in diastereomeric salts of chlorine-substituted mandelic acid and phenylethylamine.
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.
Department of Chemical and Biochemical Engineering, the University of Western Ontario London, Ontario, Canada.
Quan
Q
He
Hassan
H
Gomaa
Sohrab
S
Rohani
Jesse
J
Zhu
Michael
M
Jennings
D002713:Chlorine / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008333:Mandelic Acids / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010627:Phenethylamines / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D012995:Solubility; D013237:Stereoisomerism
D008333:Mandelic Acids; D010627:Phenethylamines; D012492:Salts; D002713:Chlorine; C037938:mandelic acid