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Updated: Jun 1, 2026
10:12
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
2-Butyl-5-pentyl-benzene-1,3-diol
Summary
This study reveals how stemphol, a natural dialkyl-resorcinol, forms molecular sheets through hydrogen bonds. These sheets arrange with alkyl chains extending outwards, impacting its physical properties.
Area of Science:
- Organic Chemistry
- Crystallography
- Natural Products
Background:
- Dialkyl-resorcinols are a class of natural compounds with diverse biological activities.
- Understanding the solid-state structure of natural products is crucial for their characterization and potential applications.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of stemphol (C15H24O2).
- To describe the packing arrangement and hydrogen bonding network in stemphol.
Main Methods:
- Single-crystal X-ray diffraction analysis was performed on stemphol.
- The crystal structure was solved and refined to determine atomic positions and bonding.
Main Results:
- Stemphol molecules form extended chains and rings via intermolecular O-H⋯O hydrogen bonds.
- These interactions create molecular sheets parallel to the (010) plane.
- The alkyl chains are oriented orthogonally to these sheets in an extended conformation.
Conclusions:
- The hydrogen bonding network dictates the self-assembly of stemphol into layered structures.
- The extended alkyl chains influence the packing density and physical properties of stemphol crystals.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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