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Comprehensive structural analysis of bromine-substituted ferrocenyl chalcones
Alejandro Burgos-Suazo1, Edwin G Ortiz-Muñoz1, Yiomaris Rodríguez-Manzano1
1University of Puerto Rico, Río Piedras Campus, College of Natural Sciences, Chemistry Department, 17 Ave. Universidad Ste. 1701, San Juan, 00925-2537, Puerto Rico.
This study details the synthesis and crystal structures of five bromine-substituted ferrocenyl chalcones. Bromine position and ferrocene attachment influence crystal packing, density, and intermolecular interactions, confirmed by Hirshfeld analysis.
Area of Science:
- Organometallic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Ferrocenyl chalcones are versatile organometallic compounds with diverse applications.
- Understanding the impact of halogen substitution on crystal packing is crucial for materials design.
- Structural characterization of novel ferrocene derivatives provides insights into structure-property relationships.
Purpose of the Study:
- To synthesize and structurally characterize five bromine-substituted ferrocenyl chalcones.
- To investigate the influence of bromine position and ferrocene connectivity on crystal packing and intermolecular interactions.
- To analyze the supramolecular features using Hirshfeld surface analysis.
Main Methods:
- Synthesis via Claisen-Schmidt condensation.
- Single-crystal X-ray diffraction for structural determination.
- Spectroscopic analysis (1H NMR, 13C NMR, IR) and melting point analysis.
- Hirshfeld surface analysis for intermolecular interactions.
Main Results:
- Three novel crystal structures of bromine-substituted ferrocenyl chalcones were determined.
- Compounds exhibit diverse crystal packing influenced by bromine substitution and ferrocene attachment.
- Intermolecular interactions involving bromine (H...Br, C...Br, Br...Br) and ferrocene units are significant.
- Hirshfeld analysis confirmed shorter contacts and increased enone participation in System 3.
Conclusions:
- The position of the bromine atom and ferrocene connectivity significantly affect crystal density and packing.
- Bromine atoms play a crucial role in mediating intermolecular interactions within the crystal lattice.
- Ferrocenyl chalcones offer tunable supramolecular architectures based on substituent variations.
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