Abstract
A suspension containing an equimolecular amount of (−)-gallocatechin-3-O-gallate (GCg) and caffeine in water was heated at 90 °C for 30 min to give a 1 : 2 complex of GCg and caffeine. X-Ray crystallographic analysis of crystal of the 1 : 2 complex showed that π–π interactions formed between the A, B′ rings of GCg and the two six-membered rings of caffeine. Whereas, the same suspension was heated at 90 °C for 30 s to give a sticky substance, which contained GCg, caffeine, and water at a molar ratio of 1 : 1 : 22 based on measurement of the integral volume of 1H-NMR signals. The sticky substance crystallized slowly to give a 2 : 2 complex of GCg and caffeine. X-Ray crystallographic analysis of crystal of the 2 : 2 complex showed that the A and C rings of GCg moieties faced each other, and face-to-face π–π interactions formed between the B ring of GCg and caffeine, the B′ ring of GCg and caffeine.
