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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Complementary halogen and hydrogen bonding: sulfur...iodine interactions and thioamide ribbons
Hadi D Arman1, Rebecca L Gieseking, Timothy W Hanks
1Department of Chemistry, Clemson University, Clemson, SC, USA.
Chemical Communications (Cambridge, England)
|March 4, 2010
Summary
Thiourea and organoiodine molecules form co-crystals with both halogen and hydrogen bonds. These co-crystals reliably create N-H...S ribbons and S...I interactions, useful in crystal engineering.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Crystallography
Background:
- Halogen bonding and hydrogen bonding are key non-covalent interactions in crystal engineering.
- Thioamide functionalities offer unique hydrogen and halogen bond accepting capabilities.
- Organoiodine compounds are versatile halogen bond donors.
Purpose of the Study:
- To investigate the co-crystallization of organoiodines with thioamide-containing molecules.
- To explore the interplay between halogen bonding and hydrogen bonding in these co-crystals.
- To identify reliable synthons for crystal engineering applications.
Main Methods:
- Co-crystallization experiments were performed using various organoiodines and thioamide derivatives.
- Single-crystal X-ray diffraction was used to determine the solid-state structures.
- Analysis of intermolecular interactions, including halogen bonds (S...I) and hydrogen bonds (N-H...S), was conducted.
Main Results:
- Co-crystals featuring both complementary halogen bonding (S...I) and hydrogen bonding (N-H...S) were successfully synthesized.
- A reliable synthon involving thiourea and organoiodine was identified, forming robust N-H...S ribbons.
- The coexistence of these interactions dictates the overall crystal packing and stability.
Conclusions:
- Thiourea-organoiodine co-crystals represent a dependable supramolecular synthon.
- The combined halogen and hydrogen bonding interactions provide a powerful strategy for designing ordered crystalline materials.
- This study offers insights into the rational design of co-crystals with predictable architectures.
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