Related Experiment Video
Updated: May 26, 2026
07:07
Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
(2-Bromo-acet-yl)ferrocene.
Acta Crystallographica. Section E, Structure Reports Online
|December 27, 2011
Summary
This study details the crystal structure of a novel iron compound, [Fe(C(5)H(5))(C(7)H(6)BrO)], revealing unique bond lengths and intermolecular interactions that form helical chains and layered structures.
Area of Science:
- Organometallic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Understanding the structural nuances of organometallic compounds is crucial for designing new materials.
- The interplay of electronic and steric factors influences metal-ligand bond lengths and molecular assembly.
- Supramolecular chemistry explores the self-assembly of molecules through non-covalent interactions.
Purpose of the Study:
- To elucidate the detailed crystal structure of the iron compound [Fe(C(5)H(5))(C(7)H(6)BrO)].
- To investigate the factors influencing Fe-C bond lengths within the molecule.
- To characterize the supramolecular architecture and intermolecular interactions in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
- Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.
- Intermolecular interactions, including hydrogen bonds (C-H⋯O) and π-π stacking, were identified and analyzed.
Main Results:
- The iron-cyclopentadienyl ligand exhibits disparate Fe-C bond lengths between substituted and unsubstituted carbon atoms.
- The bromo-acetyl group displays a syn conformation with co-planar Br and O atoms (O-C-C-Br torsion angle of 5.7°).
- Helical supramolecular chains along the b-axis are formed via C-H⋯O contacts, with a bifurcated carbonyl oxygen.
- These chains are further linked into layers by C-H⋯π(unsubstituted ring) interactions, stacking along the a-axis.
Conclusions:
- The crystal structure of [Fe(C(5)H(5))(C(7)H(6)BrO)] reveals significant structural features impacting its solid-state properties.
- Disparate Fe-C bond lengths suggest electronic or steric influences from the substituted ligand.
- The observed supramolecular assembly highlights the role of specific non-covalent interactions in directing crystal packing.
Related Concept Videos
01:07Structure of Benzene: Kekulé Model
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
01:11Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
01:15Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
01:17Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...
01:31Ferromagnetism
Materials like iron, nickel, and cobalt consist of magnetic domains, within which the magnetic dipoles are arranged parallel to each other. The magnetic dipoles are rigidly aligned in the same direction within a domain by quantum mechanical coupling among the atoms. This coupling is so strong that even thermal agitation at room temperature cannot break it. The result is that each domain has a net dipole moment. However, some materials have weaker coupling, and are ferromagnetic at lower...