Anion-pi interactions in bisadenine derivatives: a combined crystallographic and theoretical study.

Show simple item record García-Raso, Ángel Albertí Aguiló, Francisca M. Fiol Arbós, Juan Jesús Tasada Lozano, Andrés Barceló Oliver, Miquel Molins, Elies Escudero, Daniel Frontera Beccaria, Antonio Quiñonero Santiago, David Deyà Serra, Pere Maria 2018-10-08T12:17:18Z
dc.description.abstract [eng] In this manuscript we report a high-level ab initio study of anion-ð 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 ð-ð and anion-ð interactions. This pattern, i.e., coexistence of ð-ð and anion-ð 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-ð interactions. They are in strong agreement with high-level theoretical calculations.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a:
dc.relation.ispartof Inorganic Chemistry, 2007, vol. 46, num. 25, p. 10724-10735
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Anion-pi interactions in bisadenine derivatives: a combined crystallographic and theoretical study.
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion 2018-10-08T12:17:19Z info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords Noncovalent Interactions
dc.subject.keywords Ab initio calculations
dc.subject.keywords Pi interactions
dc.subject.keywords Molecular Recognition
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess

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