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3-Acetoxy-2-(acetylamino)pyridinium-1-squarate
Ibrahim Uçar1, Ahmet Bulut, Okan Zafer Yeşilel
1Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Kurupelit-Samsun, Turkey. iucar@omu.edu.tr
Summary
A novel pyridinium betaine of squaric acid was synthesized. Its crystal structure reveals intramolecular hydrogen bonding and pi-pi interactions, influencing molecular arrangement.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Squaric acid derivatives are of interest due to their unique electronic properties.
- Betaines containing pyridinium and squarate moieties offer potential for novel material applications.
Purpose of the Study:
- To synthesize and characterize a novel 3-acetoxy-2-(acetylamino)pyridinium betaine of squaric acid.
- To elucidate the crystal structure and intermolecular interactions of the synthesized compound.
Main Methods:
- Chemical synthesis of the title compound.
- Single-crystal X-ray diffraction analysis to determine the crystal structure.
- Analysis of bond distances, molecular geometry, and intermolecular interactions.
Main Results:
- Successful synthesis of the C13H10N2O6 compound.
- The crystal structure exhibits a significant twist between the pyridinium and squarate ring systems (24.0 degrees).
- A strong intramolecular hydrogen bond between the amide NH and a squarate O atom was identified, along with weak pi-pi and pi-ring interactions.
Conclusions:
- The synthesized pyridinium betaine of squaric acid possesses a unique three-dimensional structure stabilized by intramolecular hydrogen bonding.
- The observed crystal packing, influenced by pi-pi and pi-ring interactions, provides insights into the solid-state behavior of such compounds.