The function of mandelic acid as a resolving agent is investigated thr
ough a study of its 1-phenylethylammonium salts. Five different diaste
reomeric salts from the reactions of racemic 1-phenylethylamine with S
-mandelic acid have been isolated. Three of these are formed during th
e resolution of racemic 1-phenylethylamine with equimolar amount of ma
ndelic acid, and two contains the base and the acid in the molar ratio
1:3. The enantiomer of 1-phenylethylamine obtained by resolution with
S-mandelic acid depends on the base-to-acid ratio used. Through the a
nalysis of this complex system some of the aspects of mandelic acid as
a resolving agent are elucidated.