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Updated: Jun 1, 2026
14:11
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
2-(2,2,2-Trifluoro-eth-yl)isoindoline-1,3-dione
Xian-Shu Fu1, Xiao-Ping Yu, Wei-Min Wang
1College of Life Sciences, China Jiliang University, Hangzhou 310018, People's Republic of China.
Summary
This study details the crystal structure of a trifluoro-ethyl substituted isoindole compound. The research highlights the planar isoindole ring and specific molecular conformations, including weak intermolecular hydrogen bonding.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
- Isoindole derivatives are important scaffolds in medicinal chemistry and materials science.
- The influence of trifluoro-ethyl substituents on molecular geometry and intermolecular interactions requires detailed investigation.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(10)H(6)F(3)NO(2).
- To analyze the planarity of the isoindole ring system and the conformation of the trifluoro-ethyl group.
- To identify and characterize intermolecular interactions, such as hydrogen bonding, within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
- Intermolecular interactions were identified through the analysis of crystal packing and hydrogen bond geometries.
Main Results:
- The isoindole ring system in the title compound is planar, with a maximum atomic deviation of 0.012(2) Å.
- The C-C bond of the trifluoro-ethyl group exhibits a significant twist relative to the isoindole ring, with a dihedral angle of 62.58(17)°.
- Weak intermolecular interactions, specifically C-H⋯O and C-H⋯F hydrogen bonds, were observed in the crystal structure.
Conclusions:
- The crystal structure reveals a planar isoindole core, indicating electronic delocalization within the ring system.
- The observed conformation of the trifluoro-ethyl group suggests steric or electronic factors influence its orientation.
- The presence of weak hydrogen bonding plays a role in the overall crystal packing and stability of the compound.
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