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

1
Departament de Química, Universitat de les Illes Balears, Ctra. de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, Spain
2
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), c/ Til·lers, s/n, Campus UAB, 08193 Bellaterra, Spain
*
Authors to whom correspondence should be addressed.
Crystals 2019, 9(4), 224; https://doi.org/10.3390/cryst9040224
Received: 25 March 2019 / Revised: 12 April 2019 / Accepted: 24 April 2019 / Published: 25 April 2019
(This article belongs to the Special Issue Halogen-Bonded Cocrystals)
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Abstract

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. View Full-Text
Keywords: N9-ethyladenine; crystal engineering; noncovalent interactions; halogen bonding; hydrogen bonding; DFT; QTAIM; cocrystal; TFDIB N9-ethyladenine; crystal engineering; noncovalent interactions; halogen bonding; hydrogen bonding; DFT; QTAIM; cocrystal; TFDIB
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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.

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