2-(Methoxycarbonyl)phenylboronic acid

Area of Science:

• Crystallography
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Boronic acids are versatile organic compounds with applications in synthesis and materials science.
• Understanding the solid-state structure of organoboron compounds is crucial for predicting their properties and reactivity.
• Crystallographic studies provide detailed insights into molecular arrangement and intermolecular interactions.

Purpose of the Study:

• To elucidate the crystal structure of 2(CH3OCO)C6H4B(OH)2.
• To identify and characterize the different conformers present in the solid state.
• To investigate the hydrogen-bonding network and supramolecular assembly of the compound.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of crystallographic data to identify independent molecules and their conformations.
• Examination of hydrogen bonding patterns and their role in crystal packing.

Main Results:

• The title compound, C8H9BO4, crystallizes with two independent conformers (A and B) in a 1:2 ratio.
• Conformer A molecules are situated on a crystallographic mirror plane.
• A key difference lies in the orientation of the methoxycarbonyl groups, while boronic acid groups show subtle conformational variations.
• A specific hydrogen-bonding network forms layers parallel to the (100) plane.
• Within these layers, conformer B molecules form infinite chains linked by O-H...O bonds, featuring two distinct centrosymmetric dimeric motifs.

Conclusions:

• The crystal structure of 2(CH3OCO)C6H4B(OH)2 exhibits conformational polymorphism.
• The observed hydrogen-bonding network dictates the supramolecular architecture, leading to the formation of ordered chains and layers.
• This detailed structural understanding is vital for the design and application of related organoboron compounds.