Crystals | |
Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study | |
Miquel Barceló-Oliver1  Antonio Frontera1  Yannick Roselló1  Mónica Benito2  Elies Molins2  | |
[1] Departament de Química, Universitat de les Illes Balears, Ctra. de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, Spain;Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), c/ Til·lers, s/n, Campus UAB, 08193 Bellaterra, Spain; | |
关键词: N9-ethyladenine; crystal engineering; noncovalent interactions; halogen bonding; hydrogen bonding; DFT; QTAIM; cocrystal; TFDIB; | |
DOI : 10.3390/cryst9040224 | |
来源: DOAJ |
【 摘 要 】
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.
【 授权许可】
Unknown