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Updated: Jun 1, 2026
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Methyl 2-(4-chloro-benzamido)-benzoate
Summary
This study details the molecular structure of a novel chloro-amide compound. Analysis reveals specific dihedral angles and intramolecular hydrogen bonds contributing to molecular planarity and crystal chain formation.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Amide compounds are fundamental in organic chemistry, with applications ranging from pharmaceuticals to materials science.
Purpose of the Study:
- To elucidate the detailed crystal structure and molecular geometry of the title compound, C(15)H(12)ClNO(3).
- To investigate the role of intramolecular and intermolecular interactions in defining the molecule's conformation and solid-state packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of dihedral angles and hydrogen bonding networks (N-H⋯O, C-H⋯O) was performed.
Main Results:
- The central amide unit exhibited small dihedral angles (6.60(2)° and 3.42(2)°) with the attached 4-chloro-benzene and anilino rings.
- A small dihedral angle (3.32(3)°) was observed between the two benzene rings, indicating near-planarity.
- Intramolecular hydrogen bonds (N-H⋯O, C-H⋯O) formed S(6) rings, stabilizing the molecular conformation.
- Intermolecular C-H⋯O hydrogen bonds linked molecules into [010] C(7) chains in the crystal.
Conclusions:
- The investigated compound possesses a largely planar structure due to specific intramolecular interactions.
- The crystal packing is influenced by intermolecular hydrogen bonds, leading to the formation of extended chains.
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