5-Bromo-2-(phenyl-amino)-benzoic acid

Area of Science:

• Organic Chemistry
• Crystallography
• Molecular Structure

Background:

• Synthesis of novel organic compounds is crucial for materials science and drug discovery.
• Understanding molecular geometry and intermolecular interactions informs chemical property prediction.

Purpose of the Study:

• To synthesize and characterize a new organic compound, C13H10BrNO2.
• To investigate the molecular structure, including dihedral angles and hydrogen bonding.
• To analyze crystal packing and the formation of hydrogen-bonded dimers.

Main Methods:

• Chemical synthesis involving the reaction of 2,5-di-bromo-benzoic acid and aniline.
• X-ray crystallography for determining the three-dimensional molecular and crystal structure.

Main Results:

• The title compound, C13H10BrNO2, was successfully synthesized.
• The molecule exhibits a twisted conformation with a dihedral angle of 45.74(11)° between aromatic rings.
• An intramolecular N-H⋯O hydrogen bond was identified within the molecule.
• Pairwise O-H⋯O hydrogen bonds in the crystal form carboxylic acid inversion dimers.

Conclusions:

• The synthesis yielded the target compound with a distinct non-planar geometry.
• Intramolecular and intermolecular hydrogen bonding play significant roles in stabilizing the molecule and its crystal structure.
• The observed structural features provide insights into the reactivity and potential applications of this class of compounds.