Ferrocene was known as the first sandwich compound. A sandwich compound is when a metal is placed between two parallel and planar ring structures. Ferrocene has a molecular weight of 186.04 gmol, a boiling point of 249 , and a melting point of 172.5 (Mays 2). It was discovered in 1951. In 1950, R.D. Brown, a professor at the University of Melbourne, predicted that fulvalene was actually not a benzoid molecule, but an aromatic hydrocarbon as seen below.
Peter Pauson, a post-doctorate at Duquesne University in Pittsburgh, Pennsylvania, and his student, Thomas J. Kealy, tested his theory. They used FeCl3 (iron (III) chloride) to oxidize dihydrofulvalene directly to fulvalene. They created dihydrofulvalene by heating cyclopentadienylmagnesium bromide with iron (III) chloride in ether and decomposing it with iced ammonium chloride solution.
6C5H5MgBr 2FeCl33C10H10Fe 3MgBr2 3MgCl2 Fe
The final product was actually bis (cyclopentadienyl) iron (II) or C10H10Fe it was an orange solid and very stable in water, base, acid, and even with boiling (Kauffman 185). To confirm if iron was present, they boiled the compound extensively with nitric acid. The final formulation was as follows
The compound was definitely aromatic. They submitted their article to the Journal of the Chemical Society on August 7, 1951. The research team of the British Oxygen Company, Ltd, which consisted of Samuel A. Miller, John A.Tebboth, and John F. Tremaine, had actually made the same discovery in 1948 by reacting reduced iron with cyclopentadiene vapor in a nitrogen atmosphere at 300C (Kauffman, 185). However, they did not submit their article until July 11,1951.
In 1973, Geoffrey Wilkinson and Ernst Otto Fischer won the Nobel Prize in chemistry for their development work on sandwich compounds for transition metals such as iron (Kauffman 185). On April 20, 1952, Geoffrey Wilkinson, Myron Rosenblum, Mark C. Whiting, and R.B. Woodward published an article in the Journal of the American Chemical Society discussing the sandwich structure for ferrocene. It was given that name since it was similar to benzene. They favored the antiprismatic structure due to their X-ray diffraction studies. Their research was based on magnetic susceptibility, infrared absorption spectrum, and dipole moment measurements (Kauffman, 186). The structure is seen below.
Ferrocene contains 30 iron by weight and can be used as a source of iron in fuel additives (May 1). It is sold as a liquid and a solid however, when it is used in the solid form as a combustible catalyst, it produces negative results. The reason is that if its used in crumbs, there is that possibility that it may not completely dissolve. If caplets have poor dissolution rates, you will get unfavorable results (May 5). When using ferrocene as a fuel additive, it is best to dissolve it in a compatible aromatic solvent such as pyridine (May 3)
Ferrocenylated amino acids and peptides have been intensely studied in the recent past mainly due to their attractiveness as redox-active biomedical probes and structural models for peptides (tpni
ka 149). Ferrocene-amino acid conjugates such as 2-(methoxycarbonyl)methyl-2-aza 3ferrocenophane, result from ferrocene combined with an amino acid ester and a catalyst. Scientists Peter Quirk and Byron Kratochvil were able to determine the purity of ferrocene derivatives by performing oxidation with Copper (II) in acetonitrile. Copper (II) perchlorate makes an excellent titrant (Kratochvil 536). Purifying commercial ferrocene by recrystallization and sublimation makes it stable. The purity of many of the derivatives, with n-butyl and t-butylferrocene being the most pure, ranged from 93 to 100 percent (Kratochvil 536).
In conclusion, various researchers contributed to the discovery of ferrocene. Iron is the best metal for a catalytic effect. As it has already been stated, it is used as a fuel additive. It is also used to prepare amino acids and peptides. Ferrocene is also highly soluble in aromatic solvents. It is easy to see how it was the basis for a Nobel Prize.
Peter Pauson, a post-doctorate at Duquesne University in Pittsburgh, Pennsylvania, and his student, Thomas J. Kealy, tested his theory. They used FeCl3 (iron (III) chloride) to oxidize dihydrofulvalene directly to fulvalene. They created dihydrofulvalene by heating cyclopentadienylmagnesium bromide with iron (III) chloride in ether and decomposing it with iced ammonium chloride solution.
6C5H5MgBr 2FeCl33C10H10Fe 3MgBr2 3MgCl2 Fe
The final product was actually bis (cyclopentadienyl) iron (II) or C10H10Fe it was an orange solid and very stable in water, base, acid, and even with boiling (Kauffman 185). To confirm if iron was present, they boiled the compound extensively with nitric acid. The final formulation was as follows
The compound was definitely aromatic. They submitted their article to the Journal of the Chemical Society on August 7, 1951. The research team of the British Oxygen Company, Ltd, which consisted of Samuel A. Miller, John A.Tebboth, and John F. Tremaine, had actually made the same discovery in 1948 by reacting reduced iron with cyclopentadiene vapor in a nitrogen atmosphere at 300C (Kauffman, 185). However, they did not submit their article until July 11,1951.
In 1973, Geoffrey Wilkinson and Ernst Otto Fischer won the Nobel Prize in chemistry for their development work on sandwich compounds for transition metals such as iron (Kauffman 185). On April 20, 1952, Geoffrey Wilkinson, Myron Rosenblum, Mark C. Whiting, and R.B. Woodward published an article in the Journal of the American Chemical Society discussing the sandwich structure for ferrocene. It was given that name since it was similar to benzene. They favored the antiprismatic structure due to their X-ray diffraction studies. Their research was based on magnetic susceptibility, infrared absorption spectrum, and dipole moment measurements (Kauffman, 186). The structure is seen below.
Ferrocene contains 30 iron by weight and can be used as a source of iron in fuel additives (May 1). It is sold as a liquid and a solid however, when it is used in the solid form as a combustible catalyst, it produces negative results. The reason is that if its used in crumbs, there is that possibility that it may not completely dissolve. If caplets have poor dissolution rates, you will get unfavorable results (May 5). When using ferrocene as a fuel additive, it is best to dissolve it in a compatible aromatic solvent such as pyridine (May 3)
Ferrocenylated amino acids and peptides have been intensely studied in the recent past mainly due to their attractiveness as redox-active biomedical probes and structural models for peptides (tpni
ka 149). Ferrocene-amino acid conjugates such as 2-(methoxycarbonyl)methyl-2-aza 3ferrocenophane, result from ferrocene combined with an amino acid ester and a catalyst. Scientists Peter Quirk and Byron Kratochvil were able to determine the purity of ferrocene derivatives by performing oxidation with Copper (II) in acetonitrile. Copper (II) perchlorate makes an excellent titrant (Kratochvil 536). Purifying commercial ferrocene by recrystallization and sublimation makes it stable. The purity of many of the derivatives, with n-butyl and t-butylferrocene being the most pure, ranged from 93 to 100 percent (Kratochvil 536).
In conclusion, various researchers contributed to the discovery of ferrocene. Iron is the best metal for a catalytic effect. As it has already been stated, it is used as a fuel additive. It is also used to prepare amino acids and peptides. Ferrocene is also highly soluble in aromatic solvents. It is easy to see how it was the basis for a Nobel Prize.
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