Ferrocenecarboxylic acid explained

Ferrocenecarboxylic acid is the organoiron compound with the formula . 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.^[1]

Reactions and derivatives

The pK_a of ferrocenecarboxylic acid is 7.8. The acidity increases more than a thousand-fold, to pH 4.54 upon oxidation to the ferrocenium cation.^[2]

By treatment with thionyl chloride, the carboxylic acid anhydride is produced.^{[3] [4]}

Derivatives of ferrocenecarboxylic acid are components of some redox switches.

Related compounds

• 1,1'-Ferrocenedicarboxylic acid

Notes and References

1. Perry C. Reeves. 10.15227/orgsyn.056.0028. Carboxylation of Aromatic Compounds: Ferrocenecarboxylic Acid . Organic Syntheses . 1977 . 56 . 28 .
2. 10.1007/s40828-020-00119-6. The Ferrocenium/Ferrocene Couple: A Versatile Redox Switch . 2020 . Fabbrizzi . Luigi . Chemtexts . 6 . 4 . 222215803 . free .
3. 10.1107/S205322961701124X. Ferrocenecarboxylic Anhydride: Identification of a New Polymorph . 2017 . Tazi . Mehdi . Roisnel . Thierry . Mongin . Florence . Erb . William . Acta Crystallographica Section C Structural Chemistry . 73 . 10 . 760–766 . 28978780 . 4437353 .
4. 10.1021/jo01084a647. Notes- Preparation and Hydrolysis of Crystalline Ferrocenoyl Chloride . 1959 . Lau . Hans . Hart . Harold . The Journal of Organic Chemistry . 24 . 2 . 280–281 .