Halogens in Acetophenones Direct the Hydrogen Bond Docking Preference of Phenol via Stacking Interactions
| Autor: | Manuel Lange, Charlotte Zimmermann, Martin A. Suhm |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
analytical_chemistry Ketone Hydrogen bond Intermolecular force Stacking Organic chemistry Halogenation Article vibrational spectroscopy 3. Good health chemistry.chemical_compound Crystallography QD241-441 benchmark chemistry Halogen hydrogen bonds Phenyl group London dispersion molecular recognition gas phase density functional theory Acetophenone ketone complexes |
| Zdroj: | Molecules Volume 26 Issue 16 Molecules, Vol 26, Iss 4883, p 4883 (2021) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules26164883 |
| Popis: | Phenol is added to acetophenone (methyl phenyl ketone) and to six of its halogenated derivatives in a supersonic jet expansion to determine the hydrogen bonding preference of the cold and isolated 1:1 complexes by linear infrared spectroscopy. Halogenation is found to have a pronounced effect on the docking site in this intermolecular ketone balance experiment. The spectra unambiguously decide between competing variants of phenyl group stacking due to their differences in hydrogen bond strength. Structures where the phenyl group interaction strongly distorts the hydrogen bond are more difficult to quantify in the experiment. For unsubstituted acetophenone, phenol clearly prefers the methyl side despite a predicted sub-kJ/mol advantage which is nearly independent of zero point vibrational energy, turning this complex into a challenging benchmark system for electronic structure methods which include long range dispersion interactions in some way. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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