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Published on: June 13, 2022
endo-3,3-Dimethyl-4-oxobicyclo-[3.1.0]hexan-2-yl methane-sulfonate
Adrian Kremer1, Bernadette Norberg, Alain Krief
1Department of Chemistry, University of Namur, 61 Rue de Bruxelles, B-5000 Namur, Belgium.
Summary
The endo isomer of a bicyclo-hexa-nyl compound was structurally characterized. Intermolecular hydrogen bonds influence the methane-sulfonate group
Area of Science:
- Organic Chemistry
- Crystallography
- Structural Chemistry
Background:
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
- Stereochemistry plays a vital role in molecular interactions and biological activity.
- Sulfonate esters are important functional groups in organic synthesis and materials science.
Purpose of the Study:
- To determine the relative configuration and conformation of the endo isomer of a specific bicyclo-hexa-nyl methane-sulfonate.
- To investigate the role of intermolecular interactions in stabilizing the molecular conformation.
- To elucidate the crystal packing arrangement of the compound.
Main Methods:
- Single-crystal X-ray diffraction was used to establish the relative configuration and detailed molecular structure.
- Conformational analysis was performed to describe the geometry of the five-membered ring and the substituent.
- Analysis of intermolecular interactions, including hydrogen bonding, was conducted.
Main Results:
- The relative configuration of the endo isomer of C(9)H(14)O(4)S was unequivocally established.
- The five-membered ring within the molecule adopts an envelope conformation.
- Intermolecular C-H⋯O hydrogen bonds were identified as key stabilizing factors for the methane-sulfonate substituent.
- Crystal packing analysis revealed alternating layers of polar methane-sulfonate groups and stacked bicyclo-hexa-nyl rings.
Conclusions:
- The study successfully determined the stereochemistry and conformational preferences of the bicyclo-hexa-nyl methane-sulfonate.
- Intermolecular hydrogen bonding significantly influences the solid-state conformation of the methane-sulfonate group.
- The observed crystal packing provides insights into the supramolecular assembly of this class of compounds.
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