Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study
AbstractIn 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. View Full-Text
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Roselló, Y.; Benito, M.; Molins, E.; Barceló-Oliver, M.; Frontera, A. Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study. Crystals 2019, 9, 224.
Roselló Y, Benito M, Molins E, Barceló-Oliver M, Frontera A. Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study. Crystals. 2019; 9(4):224.Chicago/Turabian Style
Roselló, Yannick; Benito, Mónica; Molins, Elies; Barceló-Oliver, Miquel; Frontera, Antonio. 2019. "Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study." Crystals 9, no. 4: 224.
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