Adenine as a halogen bond acceptor: a combined experimental and DFT study
- 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.
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| Author: | Yannick Roselló, Mónica BenitoORCiDGND, Elies Molins, Miquel Barceló-Oliver, Antonio Frontera |
|---|---|
| URN: | urn:nbn:de:bvb:384-opus4-1044529 |
| Frontdoor URL | https://opus.bibliothek.uni-augsburg.de/opus4/104452 |
| ISSN: | 2073-4352OPAC |
| Parent Title (English): | Crystals |
| Publisher: | MDPI AG |
| Type: | Article |
| Language: | English |
| Year of first Publication: | 2019 |
| Publishing Institution: | Universität Augsburg |
| Release Date: | 2023/05/19 |
| Tag: | Inorganic Chemistry; Condensed Matter Physics; General Materials Science; General Chemical Engineering |
| Volume: | 9 |
| Issue: | 4 |
| First Page: | 224 |
| DOI: | https://doi.org/10.3390/cryst9040224 |
| Institutes: | Mathematisch-Naturwissenschaftlich-Technische Fakultät |
| Mathematisch-Naturwissenschaftlich-Technische Fakultät / Institut für Physik | |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Licence (German): |  CC-BY 4.0: Creative Commons: Namensnennung (mit Print on Demand) |
