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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-Amino-anilinium 2-chloro-acetate
A Srinivasa Rao1, Bharat Kumar Tripuramallu, Kishore Ravada
1School of Chemistry, University of Hyderabad, Hyderabad 500 046, India.
Summary
The crystal structure of orthophenelynediamine (OPDA) with chloroacetic acid reveals N-H⋯O hydrogen bonds forming ladder-like chains. Weak C-H⋯Cl and C-H⋯O interactions contribute to a supramolecular network.
Area of Science:
- Crystal engineering and supramolecular chemistry.
- Organic solid-state chemistry.
- Hydrogen bonding interactions.
Background:
- Orthophenelynediamine (OPDA) is a versatile organic molecule.
- Chloroacetic acid is a common organic reagent.
- Understanding intermolecular forces is crucial for crystal design.
Purpose of the Study:
- To elucidate the crystal structure of the compound formed from OPDA and chloroacetic acid.
- To investigate the role of hydrogen bonding in the supramolecular assembly.
- To characterize the network formed by intermolecular interactions.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Synthesis of the title compound via reaction of OPDA with chloroacetic acid.
- Analysis of hydrogen bonding and intermolecular interactions.
Main Results:
- The crystal structure reveals the formation of N-H⋯O hydrogen bonds, leading to ladder-like chains.
- Weak inter-molecular C-H⋯Cl interactions between anions and cations were observed.
- Additional C-H⋯O interactions further contribute to the supramolecular network.
- The compound crystallizes as C(6)H(9)N(2) (+)·ClCH(2)COO(-).
Conclusions:
- The crystal structure is stabilized by a combination of N-H⋯O, C-H⋯Cl, and C-H⋯O hydrogen bonding.
- These interactions result in a complex supramolecular network with potential implications in crystal engineering.
- The study highlights the importance of weak interactions in directing crystal packing.
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