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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2-Methyl-N-o-tolyl-benzamide.
Summary
This study details the crystal structure of a C15H15NO compound, revealing a planar amide unit and specific dihedral angles between aromatic rings. Molecular packing is influenced by hydrogen bonds and pi-interactions, forming chains.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Amide functional groups are fundamental in organic chemistry, appearing in peptides, proteins, and synthetic materials.
Purpose of the Study:
- To elucidate the detailed crystal structure of the title compound, C15H15NO.
- To analyze the planarity of the amide unit and the spatial orientation of the o-tolyl rings.
- To investigate the intermolecular interactions and packing motifs in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (hydrogen bonds, C-H...π interactions).
- Description of the unit cell and packing arrangement.
Main Results:
- The C-N-C(O)-C amide unit is planar with a root-mean-square deviation of 0.003 Å.
- Dihedral angles between the amide plane and the two o-tolyl rings are 44.71(5)° and 43.33(5)°.
- The two aromatic rings are inclined at 4.94(7)° to each other, with ortho-methyl groups in an anti orientation.
- N-H⋯O hydrogen bonds and C-H⋯π interactions link molecules into head-to-head chains along the 'a' axis.
- Independent chains pack in a herringbone pattern along the 'c' axis.
Conclusions:
- The study provides a precise structural characterization of the C15H15NO compound.
- The observed planarity and dihedral angles offer insights into the electronic and steric factors governing the molecule's conformation.
- The identified intermolecular interactions dictate the crystal packing, influencing bulk material properties.
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