Aromatic embedding wins over classical hydrogen bonding – a multi-spectroscopic approach for the diphenyl ether–methanol complex
| Autor: | Melanie Schnell, Fabian Dietrich, Jonas Altnöder, Martin A. Suhm, Markus Gerhards, Sabrina Zinn, Matthias Heger, Anke Stamm, Anja Poblotzki, Chris Medcraft, Dominic Bernhard |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Alcohol binding
Chemistry Hydrogen bond Diphenyl ether Intermolecular force General Physics and Astronomy 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology Photochemistry 01 natural sciences 0104 chemical sciences 3. Good health chemistry.chemical_compound Molecular recognition Computational chemistry ddc:540 Phenyl group Rotational spectroscopy Physical and Theoretical Chemistry 0210 nano-technology Conformational isomerism |
| Zdroj: | Physical Chemistry Chemical Physics Physical chemistry, chemical physics 18(37), 25975-25983 (2016). doi:10.1039/C6CP03557D |
| DOI: | 10.1039/C6CP03557D |
| Popis: | Dispersion interactions are omnipresent in intermolecular interactions, but their respective contributions are difficult to predict. Aromatic ethers offer competing docking sites for alcohols: the ether oxygen as a well known hydrogen bond acceptor, but also the aromatic π system. The interaction with two aromatic moieties in diphenyl ether can tip the balance towards π binding. We use a multi-spectroscopic approach to study the molecular recognition, the structure and internal dynamics of the diphenyl ether-methanol complex, employing infrared, infrared-ultraviolet and microwave spectroscopy. We find that the conformer with the hydroxy group of the alcohol binding to one aromatic π cloud and being coordinated by an aromatic C-H bond of the other phenyl group is preferred. Depending on the expansion conditions in the supersonic jet, we observe a second conformer, which exhibits a hydrogen bond to the ether oxygen and is higher in energy. |
| Databáze: | OpenAIRE |
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