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

Crystals

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