1H-Imidazol-3-ium-4-carboxyl-ate

Area of Science:

• Crystallography
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Understanding the solid-state behavior of organic molecules is crucial for materials science.
• Zwitterions, possessing both positive and negative charges, exhibit unique chemical and physical properties.
• Imidazole derivatives are important in biological systems and materials applications.

Purpose of the Study:

• To characterize the crystal structure and intermolecular interactions of a specific C4H4N2O2 compound.
• To investigate the formation of a three-dimensional supramolecular network in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of hydrogen bonding and pi-pi stacking interactions was performed.

Main Results:

• The compound exists as a zwitterion with protonated imidazole nitrogens and a deprotonated carboxylate group.
• The molecule exhibits a nearly planar conformation with a root-mean-square deviation of 0.012 Å.
• Intermolecular N-H⋯O hydrogen bonds and π-π stacking interactions (centroid-centroid distance of 3.674 Å) were identified.
• These interactions link the molecules into a 3D supramolecular network.

Conclusions:

• The crystal structure of the C4H4N2O2 compound is characterized by zwitterionic and planar molecular geometry.
• The formation of a robust 3D supramolecular network is driven by a combination of hydrogen bonding and π-π stacking.
• This detailed structural analysis provides insights into the self-assembly behavior of imidazole-containing zwitterions.