ArticleMolecules (Basel, Switzerland)2021
Halogens in Acetophenones Direct the Hydrogen Bond Docking Preference of Phenol via Stacking Interactions.
Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 13 citations in OpenAlex.
- OH-Detected Aromatic Microsolvation of an Organic NO Radical: Halogenation Controls the Solvation Side.The journal of physical chemistry. A · 2025Article
- Structural investigation of interactions between halogenated flavonoids and the lipid membrane along with their role as cytotoxic agents.Scientific reports · 2024Article
- Dispersion Control over Molecule Cohesion: Exploiting and Dissecting the Tipping Power of Aromatic Rings.Accounts of chemical research · 2024Article
- Intermolecular Forces: From Atoms and Molecules to Nanostructures.Molecules (Basel, Switzerland) · 2022Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
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 that 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.
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Registered trials
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