4-(3-Chloro-anilino)benzoic acid

Area of Science:

• Organic Chemistry
• Crystallography
• Materials Science

Background:

• The Buchwald-Hartwig reaction is a key method for forming carbon-nitrogen bonds.
• Understanding the solid-state structure of organic compounds is crucial for predicting their properties and reactivity.
• Novel molecular architectures can lead to new materials with unique characteristics.

Purpose of the Study:

• To synthesize a new organic compound with the molecular formula C13H10ClNO2.
• To investigate the crystal structure of the synthesized compound for the first time.
• To characterize the molecular conformation and intermolecular interactions in the solid state.

Main Methods:

• Synthesis of the title compound via a Buchwald-Hartwig amination reaction.
• Crystallization screening across various solvents to identify suitable crystal forms.
• Single-crystal X-ray diffraction to elucidate the precise three-dimensional molecular and crystal structure.

Main Results:

• Successful synthesis of the target compound C13H10ClNO2.
• Identification of a single, stable crystal form through solvent screening and slow evaporation.
• Determination of a highly twisted molecular conformation, with a dihedral angle of 34.66(6)° between aromatic rings.
• Observation of the formation of acid-acid dimers through intermolecular hydrogen bonding.

Conclusions:

• The study reports the first synthesis and crystal structure determination of C13H10ClNO2.
• The compound exhibits significant intramolecular twisting, influencing its solid-state packing.
• The formation of acid-acid dimers is a key feature of the crystal structure, driven by intermolecular interactions.