Related Experiment Video
Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Methyl 4-anilino-3-nitro-benzoate.
Summary
This study details the molecular structure of C(14)H(12)N(2)O(4), revealing specific aromatic ring orientation and intramolecular interactions. Crystal analysis shows intermolecular forces forming dimers, stabilized by pi-pi contacts between benzene rings.
Area of Science:
- Crystallography
- Molecular Chemistry
- Organic Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Intermolecular forces play a significant role in the bulk properties of crystalline solids, influencing their stability and packing.
- Aromatic ring interactions, such as pi-pi stacking, are fundamental in supramolecular chemistry and materials science.
Purpose of the Study:
- To elucidate the detailed molecular structure and conformation of the title compound, C(14)H(12)N(2)O(4).
- To investigate the nature and role of intramolecular and intermolecular interactions within the crystal lattice.
- To analyze the factors contributing to the stability of the crystal structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and bond parameters.
- Analysis of the crystal structure included identifying hydrogen bonding and van der Waals interactions.
- Geometric parameters, including dihedral angles and centroid-centroid distances, were calculated to characterize molecular and crystal packing.
Main Results:
- The molecule C(14)H(12)N(2)O(4) exhibits a dihedral angle of 51.50(4)° between its aromatic rings.
- An intramolecular N-H⋯O interaction forms a six-membered ring with an envelope conformation.
- Intermolecular N-H⋯O interactions lead to the formation of centrosymmetric dimers, with pi-pi contacts (3.708(1) Å) potentially stabilizing the crystal structure.
Conclusions:
- The crystal structure of C(14)H(12)N(2)O(4) is characterized by specific aromatic ring orientation and significant intermolecular interactions.
- Intramolecular hydrogen bonding dictates a particular molecular conformation, while intermolecular interactions drive crystal packing into dimers.
- The observed pi-pi contacts suggest a role in enhancing the overall stability of the crystalline solid.
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