(4-tert-Butyl-phenyl)-acetic acid

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
• Carboxylic acids and aromatic rings are fundamental functional groups in many organic compounds, influencing intermolecular interactions and crystal packing.

Purpose of the Study:

• To elucidate the detailed crystal structure of the title compound, C(12)H(16)O(2).
• To analyze the spatial relationship between the carboxylic acid group and the benzene ring.
• To investigate the packing arrangement and intermolecular interactions within the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• The crystal structure was analyzed to identify bond lengths, bond angles, and dihedral angles.
• Intermolecular interactions, specifically hydrogen bonding, were characterized.

Main Results:

• The dihedral angle between the carboxylic acid group and the benzene ring was determined to be approximately 80.9 degrees.
• The tert-butyl group displayed positional disorder, occupying two distinct sites with a ratio of approximately 0.503:0.497.
• Centrosymmetric dimers were observed, formed through intermolecular O-H⋯O hydrogen bonds between carboxylic acid groups.

Conclusions:

• The crystal structure of C(12)H(16)O(2) is characterized by a specific orientation of the carboxylic acid group relative to the benzene ring.
• The observed disorder in the tert-butyl group provides insights into the conformational flexibility of the molecule in the solid state.
• The formation of hydrogen-bonded dimers is a significant factor in the crystal packing and stability of the compound.