Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study
In this work, we report the cocrystallization of N<sup>9</sup>-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....
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MDPI AG
2019-04-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/9/4/224 |
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| author | Yannick Roselló Mónica Benito Elies Molins Miquel Barceló-Oliver Antonio Frontera |
| author_facet | Yannick Roselló Mónica Benito Elies Molins Miquel Barceló-Oliver Antonio Frontera |
| author_sort | Yannick Roselló |
| collection | DOAJ |
| description | In this work, we report the cocrystallization of N<sup>9</sup>-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. |
| first_indexed | 2024-04-11T22:21:14Z |
| format | Article |
| id | doaj.art-ad876632b03f4a6b8d6327d77f41f260 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-11T22:21:14Z |
| publishDate | 2019-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-ad876632b03f4a6b8d6327d77f41f2602022-12-22T04:00:08ZengMDPI AGCrystals2073-43522019-04-019422410.3390/cryst9040224cryst9040224Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT StudyYannick Roselló0Mónica Benito1Elies Molins2Miquel Barceló-Oliver3Antonio Frontera4Departament de Química, Universitat de les Illes Balears, Ctra. de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, SpainInstitut de Ciència de Materials de Barcelona (ICMAB-CSIC), c/ Til·lers, s/n, Campus UAB, 08193 Bellaterra, SpainInstitut de Ciència de Materials de Barcelona (ICMAB-CSIC), c/ Til·lers, s/n, Campus UAB, 08193 Bellaterra, SpainDepartament de Química, Universitat de les Illes Balears, Ctra. de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, SpainDepartament de Química, Universitat de les Illes Balears, Ctra. de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, SpainIn this work, we report the cocrystallization of N<sup>9</sup>-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.https://www.mdpi.com/2073-4352/9/4/224N<sup>9</sup>-ethyladeninecrystal engineeringnoncovalent interactionshalogen bondinghydrogen bondingDFTQTAIMcocrystalTFDIB |
| spellingShingle | Yannick Roselló Mónica Benito Elies Molins Miquel Barceló-Oliver Antonio Frontera Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study Crystals N<sup>9</sup>-ethyladenine crystal engineering noncovalent interactions halogen bonding hydrogen bonding DFT QTAIM cocrystal TFDIB |
| title | Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study |
| title_full | Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study |
| title_fullStr | Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study |
| title_full_unstemmed | Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study |
| title_short | Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study |
| title_sort | adenine as a halogen bond acceptor a combined experimental and dft study |
| topic | N<sup>9</sup>-ethyladenine crystal engineering noncovalent interactions halogen bonding hydrogen bonding DFT QTAIM cocrystal TFDIB |
| url | https://www.mdpi.com/2073-4352/9/4/224 |
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