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Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study

AuthorsRoselló, Yannick; Benito, Mónica ; Molins, Elies ; Barceló-Oliver, Miquel; Frontera, Carlos
Crystal engineering
Noncovalent interactions
Halogen bonding
Hydrogen bonding
Issue Date25-Apr-2019
PublisherMultidisciplinary Digital Publishing Institute
CitationCrystals 9(4): 224 (2019)
AbstractIn this work, we report the cocrystallization of N<sup>9</sup>-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.
Publisher version (URL)http://dx.doi.org/10.3390/cryst9040224
Appears in Collections:(ICMAB) Artículos
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