8-Quinolylguanidinium chloride

Area of Science:

• Organic Chemistry
• Crystallography
• Supramolecular Chemistry

Background:

• Quinoline derivatives are important scaffolds in medicinal chemistry and materials science.
• Guanidine moieties are known for their strong basicity and ability to form hydrogen bonds.
• Understanding the structural and electronic properties of novel heterocyclic compounds is crucial for developing new functional materials.

Purpose of the Study:

• To synthesize and characterize a new guanidine derivative of 8-amino-quinoline.
• To determine the crystal structure and analyze the intermolecular interactions of the synthesized compound.
• To investigate the conformational preferences and hydrogen bonding patterns in the guanidine-quinoline system.

Main Methods:

• Chemical synthesis involving the reaction of 8-amino-quinoline with cyanamide.
• Single-crystal X-ray diffraction to elucidate the three-dimensional crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles to describe the molecular geometry.
• Identification and analysis of intermolecular hydrogen bonds (N-H⋯Cl) and their role in crystal packing.

Main Results:

• Successful synthesis of the title compound, C(10)H(11)N(4) (+)·Cl(-).
• The crystal structure determination revealed a dihedral angle of 68.64(13)° between the guanidine group and the quinoline ring system.
• Intermolecular N-H⋯Cl hydrogen bonds were identified as the primary stabilizing force within the crystal lattice.
• The study provides precise structural data on the conformation and intermolecular interactions of this novel guanidine derivative.

Conclusions:

• The reaction of 8-amino-quinoline and cyanamide yields a novel guanidine derivative with a distinct dihedral angle between the functional groups.
• The crystal structure is predominantly stabilized by intermolecular N-H⋯Cl hydrogen bonds, highlighting their importance in directing crystal packing.
• This research contributes to the understanding of structure-property relationships in quinoline-based guanidine compounds.