(2-Butoxy-phen-yl)boronic acid

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry
• Crystallography

Background:

• Boronic acids are versatile organic compounds with applications in synthesis and materials science.
• Understanding the self-assembly behavior of organic molecules is crucial for designing novel materials.

Purpose of the Study:

• To investigate the solid-state structure and intermolecular interactions of 2-(butyloxy)phenylboronic acid.
• To elucidate the self-assembly mechanism leading to the formation of a two-dimensional array.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
• Analysis of non-covalent interactions, including hydrogen bonding, C-H⋯π, and π-π stacking, was performed.

Main Results:

• The title compound, 2-(butyloxy)phenylboronic acid, crystallizes as a centrosymmetric hydrogen-bonded dimer.
• These dimers are further organized into a two-dimensional array through a combination of C-H⋯π and π-π interactions.
• The closest C⋯C contact indicative of π-π interaction was measured at 3.540(3) Å.

Conclusions:

• 2-(butyloxy)phenylboronic acid exhibits significant self-assembly capabilities in the solid state.
• The observed 2D array formation is driven by a combination of hydrogen bonding and weaker C-H⋯π and π-π interactions.
• This study provides insights into the supramolecular assembly of functionalized phenylboronic acids.