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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
rac-Methyl 2-(2-formyl-4-nitro-phen-oxy)hexa-noate
Jun-Song Song1, De-Cai Wang, Xue-Jun He
1State Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China.
Summary
This study details the molecular structure of a racemic compound, C(14)H(17)NO(6). Researchers identified specific dihedral angles and weak hydrogen bonds influencing crystal formation in this nitroaromatic ester.
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.
- Nitroaromatic compounds and esters are important functional groups with diverse applications in pharmaceuticals and materials science.
Purpose of the Study:
- To elucidate the crystal structure and molecular conformation of the racemic title compound, C(14)H(17)NO(6).
- To investigate the intermolecular interactions, specifically hydrogen bonding, that govern the packing of these molecules in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and bond lengths/angles.
- Analysis of the crystal structure data to identify and quantify dihedral angles between key molecular fragments (benzene ring, ester group, nitro group).
- Characterization of intermolecular interactions, including hydrogen bonding, using crystallographic data and graph set notation.
Main Results:
- The crystal structure of the racemic compound C(14)H(17)NO(6) was successfully determined.
- A significant dihedral angle of 80.0(2)° was observed between the ester group's plane and the benzene ring.
- The nitro group was found to be nearly coplanar with the benzene ring, with a dihedral angle of 10.3(2)°.
- Weak aromatic C-H⋯O(nitro) hydrogen bonds were identified, leading to the formation of inversion dimers with graph set R(2)(2)(8).
Conclusions:
- The specific conformational preferences, dictated by dihedral angles, influence the molecular packing in the crystal.
- The identified weak hydrogen bonding interactions play a role in stabilizing the crystal lattice and forming supramolecular assemblies.
- This structural information provides a foundation for understanding the physical and chemical properties of this class of nitroaromatic ester compounds.
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