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assemblies of 9-methylxanthine and 9-methyluric acid have been investigated by quantum-chemical calculations. In the gas phase, the new structures are less stable than the guanine tetrad as a consequence of the absence of a cooperative effect in the former and its presence in the latter. The lack of cooperativity in the new structures can be only partly compensated by strong low-barrier hydrogen bonds (LBHB). Moreover, the new tetramers are positively charged and probably can exist only in the presence of ions.\n Similar calculations suggest that 3-methylxanthine (3MX) is a good candidate for tetrad and quadruplex structures and the existence of (3MX)n cat+ aggregates (n = 4, 8; cat+ = NH4+, Na+, K+) has been experimentally observed in the gas phase through mass spectrometry (MS) measurements. Detailed NMR studies in solution have also verified that the „internal” H-bonds (N1H...O6) in the (3MX)4 structures must be stronger than the „external” H-bonds (N7H...O2).\n In general, we found that guanine quartets (G4) are still more strongly bound than xanthine quartets (X4), despite the fact that they have the same number of hydrogen bonds. This is due to a cooperativity effect in the former case, as follows from our computational analyses. This is true not only in the gas phase but also in telomere-like structures where the quartet coordinates to two sodium ions and this complex is stacked in between two other quartets. 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