On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
| Autor: | Anita Lazić, Nemanja Trišović, Marija Petković-Benazzouz, Kristina Gak Simić, Lidija Radovanović, Ivana Okić Đorđević, Jelena Rogan, Goran V. Janjić |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Three-dimensional networks
Atoms Parallel interactions Paraffins Stacking Supramolecular chemistry chemistry.chemical_element Crystal atomic structure Crystal structure Supramolecular architectures 010402 general chemistry 01 natural sciences Hydrogen bonds Molecule General Materials Science Quantitative assessments Intermolecular interactions 010405 organic chemistry Intermolecular force Synthon General Chemistry Fluorine X ray crystallography Molecules Condensed Matter Physics 0104 chemical sciences Crystallography chemistry Electrostatic potential maps Single crystals Single crystal Quantum chemistry Quantum chemical studies Single crystal X-ray crystallography |
| Zdroj: | CrystEngComm |
| Popis: | The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HMIDLINE HORIZONTAL ELLIPSISO, C-HMIDLINE HORIZONTAL ELLIPSIS pi, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HMIDLINE HORIZONTAL ELLIPSISF interaction in the case of 2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FMIDLINE HORIZONTAL ELLIPSISF interaction in the crystal structure of 2 results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FMIDLINE HORIZONTAL ELLIPSISF interaction is absent. |
| Databáze: | OpenAIRE |
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