Ferrocenyl carboxylic acid

Ferrocenyl carboxylic acid
Names
IUPAC name
Ferrocenecarboxylic acid
Other names
FcCO2H, Ferrocenemonocarboxylic acid, Ferrocenic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.673
  • 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).
Infobox references

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]

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 ([(C5H5)Fe(C5H4CO)]2O) is produced.[5][6]

Derivatives of ferrocenecarboxylic acid are components of some redox switches.

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. S2CID 222215803.
  5. ^ 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.
  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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