Ferrocenecarboxylic acid

Names
IUPAC name

Ferrocenecarboxylic acid

Other names

FcCO2H, Ferrocenemonocarboxylic acid, Ferrocenic acid

Identifiers

CAS Number

* 1271-42-7 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 26585892

PubChem CID

* 15764230

InChI

* 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

SMILES

* [CH-]1C=CC=C1.C1=C[C-](C=C1)C(=O)O.[Fe+2]

Properties

Chemical formula

| 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

Tracking categories (test):

* SizeSet

Ferrocenecarboxylic acid is the organoiron compound with the formula (C

5)Fe(C

4CO
2H). 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]

On a two-dimensional surface, most carboxylic acids form hydrogen-bonded dimers. Ferrocenecarboxylic acid instead forms a mixture of dimers and cyclic pentamers and organizes into a quasicrystalline order with fivefold symmetry, the first known molecular quasicrystal.[3]

## Reactions and derivatives

The pKa of ferrocenecarboxylic acid is 7.79±0.08. The acidity increases more than a thousand-fold, to 4.54±0.04 upon oxidation to the ferrocenium cation.[4]

By treatment with thionyl chloride, the carboxylic acid anhydride ([(C

5)Fe(C

4CO)]
2O) is produced.[5][6]

Derivatives of ferrocenecarboxylic acid are components of some redox switches.

## Related compounds

* 1,1'-Ferrocenedicarboxylic acid
* Ferrocenecarboxaldehyde

## References

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. ↑ Wasio, Natalie A.; Quardokus, Rebecca C.; Forrest, Ryan P.; Lent, Craig S.; Corcelli, Steven A.; Christie, John A.; Henderson, Kenneth W.; Kandel, S. Alex (March 2014). "Self-assembly of hydrogen-bonded two-dimensional quasicrystals". Nature 507 (7490): 86–89. doi:10.1038/nature12993.
4. ↑ Fabbrizzi, Luigi (2020). "The Ferrocenium/Ferrocene Couple: A Versatile Redox Switch". Chemtexts 6 (4). doi:10.1007/s40828-020-00119-6.
5. ↑ Tazi, Mehdi; Roisnel, Thierry; Mongin, Florence; Erb, William (2017). "Ferrocenecarboxylic Anhydride: Identification of a New Polymorph". Acta Crystallographica Section C Structural Chemistry 73 (10): 760–766. doi:10.1107/S205322961701124X. PMID 28978780. https://hal-univ-rennes1.archives-ouvertes.fr/hal-01617956/file/Ferrocenecarboxylic anhydride -HAL.pdf.
6. ↑ 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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*[CID]: Compound ID