4-Fluoro-2-(phenyl-amino)-benzoic acid

Area of Science:

• Organic Chemistry
• Crystallography
• Supramolecular Chemistry

Background:

• The synthesis of novel organic compounds is crucial for materials science and drug discovery.
• Understanding molecular conformation and intermolecular interactions is key to predicting material properties.

Purpose of the Study:

• To synthesize and characterize a new fluorinated organic compound, C13H10FNO2.
• To investigate the crystal structure, molecular conformation, and intermolecular interactions of the synthesized compound.

Main Methods:

• Chemical synthesis involving the reaction of 2-bromo-4-fluoro-benzoic acid with aniline.
• Single-crystal X-ray diffraction analysis to determine the crystal structure and molecular geometry.
• Analysis of hydrogen bonding and other non-covalent interactions within the crystal lattice.

Main Results:

• The title compound, C13H10FNO2, was successfully synthesized.
• Two independent molecules (A and B) with slight conformational differences were identified in the asymmetric unit.
• Dihedral angles between aromatic rings were measured as 55.63(5)° and 52.65(5)°.
• Both molecules exhibit intramolecular N-H⋯O hydrogen bonds.
• The crystal structure features A-B acid-acid dimers formed by intermolecular O-H⋯O hydrogen bonds.
• Weak C-H⋯F interactions further link these dimers in the crystal.

Conclusions:

• The synthesis yielded a novel fluorinated organic molecule with interesting structural features.
• The presence of two distinct conformers in the solid state provides insights into conformational flexibility.
• The observed hydrogen bonding and C-H⋯F interactions dictate the supramolecular assembly and crystal packing.