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Updated: Jul 21, 2026
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Published on: May 27, 2018
Hydrogen-bonding patterns of two dihydroxylactone derivatives
M L Rodríguez1, M Febles, C Pérez
1Instituto de Bioorgánica, Universidad de La Laguna-CSIC, Ctra. Vieja de la Esperanza 2, 38206 La Laguna, Tenerife, Spain.
Summary
Two novel C11H16O5 compounds form distinct hydrogen-bonded chains and strands. These structures showcase unique hydroxy-to-hydroxy and hydroxy-to-carbonyl interactions, influencing their secondary structures.
Area of Science:
- Supramolecular Chemistry
- Organic Crystal Engineering
- Hydrogen Bonding Networks
Background:
- Understanding the role of hydrogen bonding in the self-assembly of organic molecules is crucial for designing functional materials.
- The specific arrangement of hydroxyl and hydroxymethyl groups significantly dictates the resulting supramolecular architecture.
- Previous studies have explored various hydrogen bonding motifs, but the comparative analysis of similar tricyclic structures offers new insights.
Purpose of the Study:
- To investigate and compare the hydrogen bonding networks in two related C11H16O5 tricyclic compounds.
- To elucidate how the presence and position of hydroxyl and hydroxymethyl groups influence the formation of secondary structures (chains, strands).
- To characterize the specific hydrogen bond interactions (hydroxy-to-hydroxy, hydroxy-to-carbonyl) driving the observed architectures.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structures of the two compounds.
- Analysis of intermolecular interactions, focusing on hydrogen bonds, was performed.
- Comparison of the hydrogen bonding patterns and resulting supramolecular assemblies was conducted.
Main Results:
- Both C11H16O5 compounds exhibit extensive hydrogen bonding networks.
- One compound forms layered structures, while the other adopts double-stranded arrangements, both leading to chain formation via hydroxy-to-hydroxy contacts.
- The hydroxymethyl group consistently acts as a hydrogen bond donor. The second hydroxyl group participates in distinct interactions: hydroxy-to-carbonyl in one structure and hydroxy-to-hydroxy in the other, leading to different secondary structures.
Conclusions:
- The study reveals how subtle differences in molecular structure, specifically the arrangement of hydroxyl groups, lead to distinct supramolecular architectures.
- The findings highlight the predictable nature of hydrogen bonding in directing the self-assembly of these tricyclic compounds into specific chains and strands.
- This research contributes to the fundamental understanding of crystal engineering principles for organic molecules with multiple hydrogen bonding sites.
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