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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4-Methyl-benzyl 4-amino-benzoate
Summary
The crystal structure of C(15)H(15)NO(2) reveals a 65.28° dihedral angle between its benzene rings. Hydrogen bonds form supramolecular chains, influencing the compound's solid-state organization.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
- The formation of intermolecular interactions, such as hydrogen bonds, dictates crystal packing and supramolecular assembly.
- The title compound, C(15)H(15)NO(2), presents an interesting scaffold for investigating molecular conformation and crystal engineering.
Purpose of the Study:
- To determine the precise molecular geometry and crystal structure of the title compound, C(15)H(15)NO(2).
- To elucidate the role of intermolecular hydrogen bonding in the self-assembly of the compound in the solid state.
- To characterize the supramolecular architecture adopted by C(15)H(15)NO(2) within its crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to collect diffraction data.
- The crystal structure was solved and refined using standard crystallographic software.
- Analysis of the crystal structure included bond length, bond angle, and torsion angle measurements, as well as hydrogen bond analysis.
Main Results:
- The dihedral angle between the two benzene rings in C(15)H(15)NO(2) was determined to be 65.28° (±0.12°).
- The crystal structure is stabilized by a network of N-H⋯N and N-H⋯O hydrogen bonds.
- These hydrogen bonds facilitate the formation of one-dimensional supramolecular chains extending along the crystallographic a-axis.
Conclusions:
- The non-planar conformation of C(15)H(15)NO(2), characterized by a significant inter-ring dihedral angle, is a key structural feature.
- Intermolecular hydrogen bonding plays a critical role in directing the self-assembly process and stabilizing the crystal structure.
- The observed supramolecular chain formation provides insights into the crystal engineering potential of this class of compounds.
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