3-Chloro-N-(4-meth-oxy-phen-yl)propanamide.

Area of Science:

• Organic Chemistry
• Crystallography
• Molecular Structure

Background:

• Secondary amides with aromatic substituents are common motifs in medicinal chemistry.
• Halogenated organic compounds often exhibit unique chemical and physical properties.
• Understanding molecular conformation and intermolecular interactions is crucial for predicting material properties.

Purpose of the Study:

• To characterize the molecular structure and crystal packing of a novel halogenated secondary amide, C(10)H(12)ClNO(2).
• To investigate the influence of halogenation and aromatic substitution on the compound's conformation.
• To elucidate the intermolecular interactions governing the crystal structure.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of torsion angles to assess electronic delocalization and conformational preferences.
• Identification and analysis of hydrogen bonding and other non-covalent interactions.

Main Results:

• The crystal structure of C(10)H(12)ClNO(2) was successfully determined.
• A specific C(=O)-N(H)-C(ar)-C(ar) torsion angle of -33.70(18)° was observed, indicating limited resonance.
• Molecules are organized into chains along the a axis via classical N-H⋯O and C-H⋯O hydrogen bonds.

Conclusions:

• The observed torsion angle suggests a lack of significant resonance delocalization between the amide and aromatic systems.
• Intermolecular hydrogen bonding plays a key role in the crystal packing of this halogenated amide.
• The structural findings provide a foundation for understanding the reactivity and properties of related compounds.