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Selective solvent inclusion as a tool for mapping molecular properties in crystal structures: a diethylstilbestrol
1Department of Chemistry, University of Oslo, PO Box 1033 Blindern, N-0315 Oslo, Norway. c.h.gorbitz@kjemi.uio.no
Acta Crystallographica. Section B, Structural Science
|December 2, 2000
Summary
Cocrystallization with solvents reveals stronger hydrogen bonds and more C-H.pi interactions in diethylstilbestrol (DES) crystal structures. This method also highlights the hydrogen-bond donating abilities of common organic solvents.
Area of Science:
- Supramolecular Chemistry
- Crystallography
- Organic Chemistry
Background:
- Cocrystallization with solvents is a valuable technique for understanding molecular interactions.
- Diethylstilbestrol (DES) is a synthetic estrogen with known biological activity.
Purpose of the Study:
- To investigate the role of solvent molecules in the crystal structures of diethylstilbestrol (DES).
- To analyze the impact of solvent inclusion on hydrogen bonding and hydrophobic interactions in DES solvates.
Main Methods:
- Cocrystallization of DES with nine different solvent molecules.
- X-ray diffraction analysis of the resulting DES solvate crystal structures.
- Comparison of experimental crystal conformations with molecular mechanics calculations.
Main Results:
- Solvent inclusion enhanced the strength and number of hydrogen bonds in DES crystals.
- Increased favorable C-H.pi interactions were observed between DES molecules upon solvent inclusion.
- Solvents like DMSO, DMF, acetonitrile, and acetone exhibited significant hydrogen-bond donating properties.
- Observed molecular conformations in crystals aligned well with molecular mechanics predictions.
Conclusions:
- Cocrystallization is an effective method for probing intermolecular interactions and conformational preferences.
- Solvent choice can significantly influence crystal packing and intermolecular forces in DES solvates.
- Understanding these interactions is crucial for designing new materials and pharmaceuticals.
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