8-Iodo-quinolinium chloride dihydrate.

Area of Science:

• Organic Chemistry
• Crystallography
• Chemical Synthesis

Background:

• 8-iodo-quinoline is a key intermediate in organic synthesis.
• The Sandmeyer reaction is a well-established method for introducing halogens onto aromatic rings.
• Understanding the structural properties of iodo-quinoline derivatives is important for their applications.

Purpose of the Study:

• To synthesize and characterize 8-iodo-quinolinium chloride dihydrate.
• To elucidate the crystal structure and intermolecular interactions of the title compound.
• To investigate the packing arrangement and hydrogen bonding in the crystal lattice.

Main Methods:

• Sandmeyer reaction for synthesis of 8-iodo-quinoline.
• Single-crystal X-ray diffraction for structural analysis.
• Analysis of hydrogen bonding and π-π stacking interactions.

Main Results:

• The title compound, C(9)H(7)IN(+)·Cl(-)·2H(2)O, was successfully synthesized.
• The crystal structure revealed an almost planar 8-iodo-quinolinium ion.
• Solvent water molecules and chloride ions form a hydrogen-bonded chain along the c axis.
• Cationic aromatic π-π stacking was observed between adjacent 8-iodo-quinolinium ions.
• Hydrogen bonds link the quinolinium ions to the water-chloride chain.

Conclusions:

• The Sandmeyer reaction provides an effective route to 8-iodo-quinolinium chloride dihydrate.
• The crystal structure is stabilized by a combination of hydrogen bonding and π-π stacking.
• The observed structural features provide insights into the solid-state behavior of iodo-quinoline derivatives.