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Ferrocenecarboxylic acid

From Wikipedia, the free encyclopedia
Ferrocenecarboxylic acid
Names
IUPAC name
Ferrocenecarboxylic acid
Other names
Ferrocenemonocarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.673 Edit this at Wikidata
  • InChI=1S/C6H5O2.C5H5.Fe/c7-6(8)5-3-1-2-4-5;1-2-4-5-3-1;/h1-4H,(H,7,8);1-5H;/q2*-1;+2
    Key: BAJHDUZEIKRKAS-UHFFFAOYSA-N
  • [CH-]1C=CC=C1.C1=C[C-](C=C1)C(=O)O.[Fe+2]
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).

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]

Reactions and derivatives

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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.

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References

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  1. ^ 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.
  2. ^ Perry C. Reeves (1977). "Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid". Organic Syntheses. 56: 28. doi:10.15227/orgsyn.056.0028.
  3. ^ Fabbrizzi, Luigi (2020). "The Ferrocenium/Ferrocene Couple: A Versatile Redox Switch". Chemtexts. 6 (4). doi:10.1007/s40828-020-00119-6. S2CID 222215803.
  4. ^ 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.
  5. ^ 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.