Objective
The purpose of the experiment is to synthesize a compound with an organometallic iron-carbon bond and use infrared spectroscopy to investigate the unconventional sandwich structure. In addition, the experiment aims to understand pi-bonding of an arene ring, use cyclic voltammetry to understand the redox capacity of ferrocene, and explore the barriers between formal inorganic and organic chemistry definitions.
Introduction
Ferrocene was discovered unintentionally in 1949 when Miller, Tebboth, and Tremaine from British Oxygen tried to synthesize amines from hydrocarbons as a modification of the Haber process.1 Their work and discovery was published three years later in 1952, but they did not deduce the pentahapto sandwich structure.1 Woodward and Wilkinson determined the structure based on its reactivity, and their discovery led to a newfound interest in structures containing d-block metals and hydrocarbons.2
Ferrocene, as shown in Figure 1, is an organometallic compound consisting of two cyclopentadienyl (Cp) rings attached to opposite sides of iron. The “η5” hapticity indicates that five atoms from the Cp ligand are coordinating to the iron ion. The iron contributes six electrons with it’s oxidation state of 2+, and the Cp rings each contribute six electrons. Thus, the total electron count of …show more content…
In Figure 9, the peak at approximately 4.0 ppm is attributed to the protons in ferrocene. Since cyclopentadienyl rings have symmetry and protons that are chemically equivalent, there is only one signal. The rotation of the rings around the iron center yields rapid equilibration of the protons in ferrocene.6 There are no neighboring protons, so the signal is a singlet. The other peak at approximately 2.0 ppm is due to the presence of H2O. This indicates that the ferrocene was not completely dry and there were traces of water in the sample tested for
The purpose of the experiment is to synthesize a compound with an organometallic iron-carbon bond and use infrared spectroscopy to investigate the unconventional sandwich structure. In addition, the experiment aims to understand pi-bonding of an arene ring, use cyclic voltammetry to understand the redox capacity of ferrocene, and explore the barriers between formal inorganic and organic chemistry definitions.
Introduction
Ferrocene was discovered unintentionally in 1949 when Miller, Tebboth, and Tremaine from British Oxygen tried to synthesize amines from hydrocarbons as a modification of the Haber process.1 Their work and discovery was published three years later in 1952, but they did not deduce the pentahapto sandwich structure.1 Woodward and Wilkinson determined the structure based on its reactivity, and their discovery led to a newfound interest in structures containing d-block metals and hydrocarbons.2
Ferrocene, as shown in Figure 1, is an organometallic compound consisting of two cyclopentadienyl (Cp) rings attached to opposite sides of iron. The “η5” hapticity indicates that five atoms from the Cp ligand are coordinating to the iron ion. The iron contributes six electrons with it’s oxidation state of 2+, and the Cp rings each contribute six electrons. Thus, the total electron count of …show more content…
In Figure 9, the peak at approximately 4.0 ppm is attributed to the protons in ferrocene. Since cyclopentadienyl rings have symmetry and protons that are chemically equivalent, there is only one signal. The rotation of the rings around the iron center yields rapid equilibration of the protons in ferrocene.6 There are no neighboring protons, so the signal is a singlet. The other peak at approximately 2.0 ppm is due to the presence of H2O. This indicates that the ferrocene was not completely dry and there were traces of water in the sample tested for