Adenine as a Halogen Bond Acceptor: A combined experimental and DFT study

Show simple item record Roselló, Yannick Benito, Mónica Molins, Elies Barceló Oliver, Miquel Frontera Beccaria, Antonio 2019-05-02T08:03:53Z 2019-05-02T08:03:53Z
dc.description.abstract [eng] In this work, we report the cocrystallization of N9-ethyladenine with 1,2,4,5-tetrafluoro-3,6- diiodobenzene (TFDIB), a classical XB donor. As far as our knowledge extends, this is the first cocrystal reported to date where an adenine derivative acts as a halogen bond acceptor. In the solid state, each adenine ring forms two centrosymmetric H-bonded dimers: one using N1···HA6-N6 and the other N7···HB6-N6. Therefore, only N3 is available as a halogen bond acceptor that, indeed, establishes an N···I halogen bonding interaction with TFDIB. The H-bonded dimers and halogen bonds have been investigated via DFT (Density Functional Theory) calculations and the Bader's Quantum Theory of Atoms In Molecules (QTAIM) method at the B3LYP/6-311+G* level of theory. The influence of H-bonding interactions on the lone pair donor ability of N3 has also been analyzed using the molecular electrostatic potential (MEP) surface calculations.
dc.format application/pdf
dc.relation.ispartof Crystals, 2019, vol. 9, p. 224
dc.rights , 2019
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Adenine as a Halogen Bond Acceptor: A combined experimental and DFT study
dc.type info:eu-repo/semantics/article 2019-05-02T08:03:53Z
dc.rights.accessRights info:eu-repo/semantics/openAccess

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