Structure of Diferrocenyl Thioketone: From Molecule to Crystal
Ferrocenyl-functionalized thioketones have recently been recognized as useful building blocks for sulfur-containing compounds with potential applications in materials chemistry. This work is devoted to a single representative of such thioketones, namely diferrocenyl thioketone (Fc<sub>2</su...
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/21/3950 |
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| author | Piotr Matczak Grzegorz Mlostoń Róża Hamera-Fałdyga Helmar Görls Wolfgang Weigand |
| author_facet | Piotr Matczak Grzegorz Mlostoń Róża Hamera-Fałdyga Helmar Görls Wolfgang Weigand |
| author_sort | Piotr Matczak |
| collection | DOAJ |
| description | Ferrocenyl-functionalized thioketones have recently been recognized as useful building blocks for sulfur-containing compounds with potential applications in materials chemistry. This work is devoted to a single representative of such thioketones, namely diferrocenyl thioketone (Fc<sub>2</sub>CS), whose structure has been determined here for the first time. Both X-ray crystallography and a wide variety of quantum-chemical methods were used to explore the structure of Fc<sub>2</sub>CS. In addition to the X-ray structure determination, intermolecular interactions occurring in the crystal structure of Fc<sub>2</sub>CS were examined in detail by quantum-chemical methods. These methods were also an invaluable tool in studying the molecular structure of Fc<sub>2</sub>CS, from the gas phase to solutions and to its crystal. Intramolecular interactions governing the conformational behavior of an isolated Fc<sub>2</sub>CS molecule were deduced from quantum-chemical analyses carried out in orbital space and real space. Our experimental and theoretical results indicate that the main structural features of an isolated Fc<sub>2</sub>CS molecule in its lowest-energy geometry are retained both upon solvation and in the crystal. The tilt of ferrocenyl groups is only slightly affected by crystal packing forces that are dominated by dispersion. Nonetheless, a network of intermolecular interactions, such as H···H, C···H and S···H, was detected in the Fc<sub>2</sub>CS crystal but each of them is fairly weak. |
| first_indexed | 2024-12-13T06:27:09Z |
| format | Article |
| id | doaj.art-63051e65ec674b3aa0e85f1b8dc03497 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T06:27:09Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-63051e65ec674b3aa0e85f1b8dc034972022-12-21T23:56:42ZengMDPI AGMolecules1420-30492019-10-012421395010.3390/molecules24213950molecules24213950Structure of Diferrocenyl Thioketone: From Molecule to CrystalPiotr Matczak0Grzegorz Mlostoń1Róża Hamera-Fałdyga2Helmar Görls3Wolfgang Weigand4Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90236 Lodz, PolandDepartment of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91403 Lodz, PolandDepartment of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91403 Lodz, PolandInstitute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Humboldtstrasse 8, 07743 Jena, GermanyInstitute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Humboldtstrasse 8, 07743 Jena, GermanyFerrocenyl-functionalized thioketones have recently been recognized as useful building blocks for sulfur-containing compounds with potential applications in materials chemistry. This work is devoted to a single representative of such thioketones, namely diferrocenyl thioketone (Fc<sub>2</sub>CS), whose structure has been determined here for the first time. Both X-ray crystallography and a wide variety of quantum-chemical methods were used to explore the structure of Fc<sub>2</sub>CS. In addition to the X-ray structure determination, intermolecular interactions occurring in the crystal structure of Fc<sub>2</sub>CS were examined in detail by quantum-chemical methods. These methods were also an invaluable tool in studying the molecular structure of Fc<sub>2</sub>CS, from the gas phase to solutions and to its crystal. Intramolecular interactions governing the conformational behavior of an isolated Fc<sub>2</sub>CS molecule were deduced from quantum-chemical analyses carried out in orbital space and real space. Our experimental and theoretical results indicate that the main structural features of an isolated Fc<sub>2</sub>CS molecule in its lowest-energy geometry are retained both upon solvation and in the crystal. The tilt of ferrocenyl groups is only slightly affected by crystal packing forces that are dominated by dispersion. Nonetheless, a network of intermolecular interactions, such as H···H, C···H and S···H, was detected in the Fc<sub>2</sub>CS crystal but each of them is fairly weak.https://www.mdpi.com/1420-3049/24/21/3950ferrocenethioketonemolecular structurecrystal structurexrd crystallographyquantum-chemical calculation |
| spellingShingle | Piotr Matczak Grzegorz Mlostoń Róża Hamera-Fałdyga Helmar Görls Wolfgang Weigand Structure of Diferrocenyl Thioketone: From Molecule to Crystal Molecules ferrocene thioketone molecular structure crystal structure xrd crystallography quantum-chemical calculation |
| title | Structure of Diferrocenyl Thioketone: From Molecule to Crystal |
| title_full | Structure of Diferrocenyl Thioketone: From Molecule to Crystal |
| title_fullStr | Structure of Diferrocenyl Thioketone: From Molecule to Crystal |
| title_full_unstemmed | Structure of Diferrocenyl Thioketone: From Molecule to Crystal |
| title_short | Structure of Diferrocenyl Thioketone: From Molecule to Crystal |
| title_sort | structure of diferrocenyl thioketone from molecule to crystal |
| topic | ferrocene thioketone molecular structure crystal structure xrd crystallography quantum-chemical calculation |
| url | https://www.mdpi.com/1420-3049/24/21/3950 |
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