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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
(2-Chloro-3,5-dinitro-phen-yl)(piperidin-1-yl)methanone
Xun Luo1, Yun-Chuang Huang, Chao Gao
1State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China.
Summary
The crystal structure of a novel compound reveals a piperidine ring in a chair conformation. Molecular analysis shows varied nitro group orientations and stabilization through π-π stacking interactions in its crystal packing.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Piperidine derivatives are common scaffolds in medicinal chemistry and materials science.
- Nitroaromatic compounds exhibit diverse electronic and structural characteristics.
Purpose of the Study:
- To elucidate the crystal structure and molecular conformation of the title compound, C(12)H(12)ClN(3)O(5).
- To investigate the spatial orientation of nitro groups relative to the aromatic ring.
- To analyze the intermolecular interactions governing crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Conformational analysis of the piperidine ring was performed.
- Intermolecular interactions, specifically π-π stacking, were quantified based on crystallographic data.
Main Results:
- The piperidine ring was found to adopt a chair conformation.
- One nitro group was nearly coplanar with the aromatic ring (torsion angle -1.4°), while the other was significantly twisted (torsion angle 34.7°).
- Crystal packing is stabilized by intermolecular π-π stacking interactions with a centroid-centroid distance of 3.579 Å.
Conclusions:
- The study provides detailed structural insights into a novel chlorinated nitro-substituted piperidine derivative.
- The observed conformational flexibility of the nitro groups influences crystal packing.
- Intermolecular π-π stacking plays a significant role in the stabilization of the crystal lattice.
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