The
liquid-assisted grinding cocrystallization of theophylline
with benzamide leading to polymorphic compounds was investigated.
A solvent screening with 17 different solvents was performed. The
dipole moment of the solvent used in the synthesis determines the
structure of the polymorphic product. A detailed investigation leads
to the determination of the kinetically and thermodynamically favored
product. In situ observations of the formation pathway during the
grinding process of both polymorphs show that the thermodynamically
favored cocrystal is formed in a two-step mechanism with the kinetic
cocrystal as an intermediate.
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