The interaction of caffeine with L-tryptophan was investigated in aqueous solution adjusted to an ionic strength of 0.20, at pH 6.2, by using 1H NMR spectroscopy. Caffeine interacted with L-tryptophan at a molar ratio of 1:1 by parallel stacking. The thermodynamic parameters obtained for the complexation were as follows: delta G degree = -1.70 kcal/mol at 25 degrees C (K = 17.6 M-1), delta H degree = -3.7 kcal/mol, delta S degree = -6.7 eu. It was found that the driving force for parallel stacking is a combination of electrostatic, polarization, and dispersion interactions, and the contribution of hydrophobic bonding is not large. A possible stacking mode is postulated based on the complexation shifts and pi-electron charge distributions of caffeine and L-tryptophan.
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