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Updated: Jul 16, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Strong structuring arising from weak cooperative O-H···π and C-H···O hydrogen bonding in benzene-methanol solution
Camilla Di Mino1, Andrew G Seel2, Adam J Clancy3
1Department of Physics and Astronomy, University College London, London, WC1E 6BT, UK.
Weak hydrogen bonds, like O-H···π and C-H···O, guide molecular interactions. This study reveals how these bonds create ordered structures in liquid benzene-methanol mixtures, observed using neutron diffraction.
Area of Science:
- Physical Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Weak hydrogen bonds (e.g., O-H···π, C-H···O) are crucial for molecular assembly and recognition.
- These interactions are challenging to observe and characterize in liquid solutions.
Purpose of the Study:
- To investigate the spatial and orientational structure of benzene-methanol mixtures.
- To elucidate the role of weak hydrogen bonds in templating liquid-phase structures.
Main Methods:
- Neutron diffraction was employed to study benzene-methanol mixtures.
- Hydrogen-deuterium (H/D) isotopic substitution was used to enhance structural analysis.
Main Results:
- Methanol molecules fully solvate benzene, forming a highly localized and directional O-H···π interaction.
- Methanol's intrinsic tendency to form motifs is imprinted on the solvation structure around benzene.
- Bifurcated hydrogen bonds between methanol oxygens and benzene C-H groups were observed.
Conclusions:
- Weak hydrogen bonds can significantly influence and order stronger interactions in liquid phases.
- Cooperative structural motifs driven by weak hydrogen bonding persist in solution.
- This provides direct evidence of weak hydrogen bond-directed organization in liquid mixtures.
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