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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

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4-(2-Benzoyl-ethyl)benzoic acid.

Roger A Lalancette¹, Hugh W Thompson

¹Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102, USA.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study reveals the molecular conformation and dimerization of a C(16)H(14)O(3) compound. It forms hydrogen-bonded dimers through carboxyl pairing, influencing crystal packing via C-H⋯O interactions.

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding molecular conformation is crucial for predicting chemical properties.
Dimerization and intermolecular interactions dictate crystal packing and material characteristics.

Purpose of the Study:

To elucidate the three-dimensional molecular structure of the title compound (C(16)H(14)O(3)).
To investigate the dimerization behavior and intermolecular interactions in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, angles, and intermolecular contacts.

Main Results:

The compound exhibits a conformation where functional groups are nearly coplanar with adjacent rings.

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A significant dihedral angle of 78.51° exists between the two aromatic rings.

Centrosymmetric hydrogen-bonded carboxyl pairing was observed, with O⋯O distance of 2.6218 Å and O-H⋯O angle of 176°.

Two intermolecular C-H⋯O contacts involving the ketone group were identified in the crystal packing.

Conclusions:

The study provides detailed insights into the solid-state structure of the C(16)H(14)O(3) compound.
Hydrogen bonding and van der Waals forces play key roles in the observed crystal packing.
The conformational preferences and dimerization behavior are critical for understanding its supramolecular assembly.