Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds
Perfluorophenyl-substituted compounds, 3-hydroxy-1,3-bis(pentafluorophenyl)-2- propen-1-one (H<b>1</b>) and 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one (H<sub>2</sub><b>2</b>), were prepared in 56 and 30% yields, respectively, and only the enol fo...
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MDPI AG
2019-03-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/9/3/175 |
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| author | Takumi Kusakawa Shunichiro Sakai Kyosuke Nakajima Hidetaka Yuge Izabela I. Rzeznicka Akiko Hori |
| author_facet | Takumi Kusakawa Shunichiro Sakai Kyosuke Nakajima Hidetaka Yuge Izabela I. Rzeznicka Akiko Hori |
| author_sort | Takumi Kusakawa |
| collection | DOAJ |
| description | Perfluorophenyl-substituted compounds, 3-hydroxy-1,3-bis(pentafluorophenyl)-2- propen-1-one (H<b>1</b>) and 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one (H<sub>2</sub><b>2</b>), were prepared in 56 and 30% yields, respectively, and only the enol forms were preferentially obtained among the keto-enol tautomerism. Molecular conformations and tautomerism of the fluorine-substituted compounds were certified based on X-ray crystallographic studies and density functional calculations. The solvent dependency of the absorption spectra was only observed for the fluorinated compounds. The compounds H<b>1</b> and H<sub>2</sub><b>2</b> quantitatively formed co-crystals with the corresponding non-perfluorinated compounds, dibenzoylmethane (H<b>3</b>) and 1,5-dihydroxy-1,5-diphenyl-1,4-pentadien-3-one (H<sub>2</sub><b>4</b>), respectively, through the arene–perfluoroarene interaction to give the 1:1 co-crystals H<b>1</b>•H<b>3</b> and H<sub>2</sub><b>2</b>•H<sub>2</sub><b>4</b>, which were characterized by X-ray crystallographic and elemental analysis studies. |
| first_indexed | 2024-04-11T10:58:20Z |
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| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-11T10:58:20Z |
| publishDate | 2019-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-1fa2ad3217cb4388ab5818dfd5a1ecd12022-12-22T04:28:41ZengMDPI AGCrystals2073-43522019-03-019317510.3390/cryst9030175cryst9030175Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone CompoundsTakumi Kusakawa0Shunichiro Sakai1Kyosuke Nakajima2Hidetaka Yuge3Izabela I. Rzeznicka4Akiko Hori5Graduate School of Engineering and Science, Shibaura Institute of Technology, Fukasaku 307, Minuma-ku, Saitama 337-8570, JapanDepartment of Chemistry, School of Science, Kitasato University, Kitasato 1-15-1, Minami-ku, Sagamihara 252-0373, JapanDepartment of Chemistry, School of Science, Kitasato University, Kitasato 1-15-1, Minami-ku, Sagamihara 252-0373, JapanDepartment of Chemistry, School of Science, Kitasato University, Kitasato 1-15-1, Minami-ku, Sagamihara 252-0373, JapanGraduate School of Engineering and Science, Shibaura Institute of Technology, Fukasaku 307, Minuma-ku, Saitama 337-8570, JapanGraduate School of Engineering and Science, Shibaura Institute of Technology, Fukasaku 307, Minuma-ku, Saitama 337-8570, JapanPerfluorophenyl-substituted compounds, 3-hydroxy-1,3-bis(pentafluorophenyl)-2- propen-1-one (H<b>1</b>) and 1,5-dihydroxy-1,5-bis(pentafluorophenyl)-1,4-pentadien-3-one (H<sub>2</sub><b>2</b>), were prepared in 56 and 30% yields, respectively, and only the enol forms were preferentially obtained among the keto-enol tautomerism. Molecular conformations and tautomerism of the fluorine-substituted compounds were certified based on X-ray crystallographic studies and density functional calculations. The solvent dependency of the absorption spectra was only observed for the fluorinated compounds. The compounds H<b>1</b> and H<sub>2</sub><b>2</b> quantitatively formed co-crystals with the corresponding non-perfluorinated compounds, dibenzoylmethane (H<b>3</b>) and 1,5-dihydroxy-1,5-diphenyl-1,4-pentadien-3-one (H<sub>2</sub><b>4</b>), respectively, through the arene–perfluoroarene interaction to give the 1:1 co-crystals H<b>1</b>•H<b>3</b> and H<sub>2</sub><b>2</b>•H<sub>2</sub><b>4</b>, which were characterized by X-ray crystallographic and elemental analysis studies.https://www.mdpi.com/2073-4352/9/3/175co-crystalselectrostatic interactionsfluorineketo-enol form |
| spellingShingle | Takumi Kusakawa Shunichiro Sakai Kyosuke Nakajima Hidetaka Yuge Izabela I. Rzeznicka Akiko Hori Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds Crystals co-crystals electrostatic interactions fluorine keto-enol form |
| title | Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds |
| title_full | Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds |
| title_fullStr | Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds |
| title_full_unstemmed | Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds |
| title_short | Synthesis, Structures and Co-Crystallizations of Perfluorophenyl Substituted β-Diketone and Triketone Compounds |
| title_sort | synthesis structures and co crystallizations of perfluorophenyl substituted β diketone and triketone compounds |
| topic | co-crystals electrostatic interactions fluorine keto-enol form |
| url | https://www.mdpi.com/2073-4352/9/3/175 |
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