Ferrocenecarboxylic acid
Ferrocenecarboxylic acid is the organoiron compound with the formula (C5H5)Fe(C5H4CO2H). It is the simplest carboxylic acid derivative of ferrocene. It can be prepared in two steps from ferrocene by acylation with a 2-chlorobenzoyl chloride followed by hydrolysis.[2]
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Names | |
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IUPAC name
Ferrocenecarboxylic acid | |
Other names
Ferrocenemonocarboxylic acid | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.013.673 |
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C11H10FeO2 | |
Molar mass | 230.044 g·mol−1 |
Appearance | yellow solid |
Density | 1.862 g/cm3[1] |
Melting point | 214–216 °C (417–421 °F; 487–489 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references |
Reactions and derivatives
The pKa of ferrocenecarboxylic acid is 7.8. The acidity increases more than a thousand-fold, to pH 4.54 upon oxidation to the ferrocenium cation.[3]
By treatment with thionyl chloride, the carboxylic acid anhydride ([(C5H5)Fe(C5H4CO)]2O) is produced.[4][5]
Derivatives of ferrocenecarboxylic acid are components of some redox switches.
Related compounds
References
- Lin, Lily; Berces, Attila; Kraatz, Heinz-Bernhard (1998). "Ferrocenic acid derivatives: Towards Rationalizing Changes in the Electronic and Geometric Structures". Journal of Organometallic Chemistry. 556 (1–2): 11–20. doi:10.1016/S0022-328X(97)00785-7.
- Perry C. Reeves (1977). "Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid". Organic Syntheses. 56: 28. doi:10.15227/orgsyn.056.0028.
- Fabbrizzi, Luigi (2020). "The Ferrocenium/Ferrocene Couple: A Versatile Redox Switch". Chemtexts. 6 (4). doi:10.1007/s40828-020-00119-6. S2CID 222215803.
- Tazi, Mehdi; Roisnel, Thierry; Mongin, Florence; Erb, William (2017). "Ferrocenecarboxylic Anhydride: Identification of a New Polymorph" (PDF). Acta Crystallographica Section C Structural Chemistry. 73 (10): 760–766. doi:10.1107/S205322961701124X. PMID 28978780. S2CID 4437353.
- Lau, Hans; Hart, Harold (1959). "Notes- Preparation and Hydrolysis of Crystalline Ferrocenoyl Chloride". The Journal of Organic Chemistry. 24 (2): 280–281. doi:10.1021/jo01084a647.
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