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Updated: Jul 10, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Anion-pi interactions in bisadenine derivatives: a combined crystallographic and theoretical study
Angel Garcia-Raso1, Francisca M Albertí, Juan J Fiol
1Department of Chemistry, Universitat de les Illes Balears, Crta. de Valldemossa km 7.5, E-07122 Palma de Mallorca, Spain.
Abstract:
In this manuscript we report a high-level ab initio study of anion-pi interactions involving N9-methyl-adenine, N6-methyl-adenine, N9-methyl-hypoxanthine, a dimer of N9-methyl-adenine, and N9,N9'-trimethylene-bisadenine. DNA bases like adenine are electron-deficient arenes that are well suited for interacting favorably with anions. We demonstrate that these compounds are able to interact favorably with anions. N9-Methyl-adenine, N6-methyl-adenine, and the dimer of N9-methyl-adenine interact with the anion via the six-membered ring more strongly than adenine due to cooperativity effects between the noncovalent pi-pi and anion-pi interactions. This pattern, i.e., coexistence of pi-pi and anion-pi bonding, is observed experimentally in the solid state. Finally, we report the solid-state characterization of two new compounds N6,N6'-dimethylene-bisadenine hydrochloride and an outer-sphere complex of protonated N9,N9'-trimethylene-bishypoxanthine with zinc tetrachloride anion, that exhibit interesting anion-pi interactions. They are in strong agreement with high-level theoretical calculations.
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