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

Show simple item record

dc.contributor.author García-Raso, Ángel
dc.contributor.author Albertí Aguiló, Francisca M.
dc.contributor.author Fiol Arbós, Juan Jesús
dc.contributor.author Tasada Lozano, Andrés
dc.contributor.author Barceló Oliver, Miquel
dc.contributor.author Molins, Elies
dc.contributor.author Escudero, Daniel
dc.contributor.author Frontera Beccaria, Antonio
dc.contributor.author Quiñonero Santiago, David
dc.contributor.author Deyà Serra, Pere Maria
dc.date.accessioned 2018-10-08T12:17:18Z
dc.identifier.uri http://hdl.handle.net/11201/147996
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: https://doi.org/10.1021/ic701555n
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
dc.date.updated 2018-10-08T12:17:19Z
dc.date.embargoEndDate 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
dc.identifier.doi https://doi.org/10.1021/ic701555n


Files in this item

This item appears in the following Collection(s)

Show simple item record