Interaction of theobromine with sodium benzoate

The interaction of theobromine with sodium benzoate was investigated by PMR spectroscopy. The interaction of theobromine with pentadeuterated benzoic acid (benzoic acid-d5) was examined in the same manner but to a lesser degree. Chemical shifts of theobromine protons were determined as a function of sodium benzoate concentration in deuterium oxide at 30 and 15 degrees. Signals of both methyl groups of theobromine underwent significant upfield shifts when sodium benzoate was added to a theobromine solution. This fact suggests that a complex is formed by vertical stacking or plane-to-plane stacking. The same results were obtained for benzoic acid-d5.