2,5-Dihydroxy-1,4-benzoquinone

2,5-Dihydroxy-1,4-benzoquinone
Names
IUPAC name
2,5-Dihydroxycyclohexa-2,5-diene-1,4-dione
Other names
2,5-Dihydroxy-p-benzoquinone, anilic acid
Identifiers
615-94-1
3D model (Jmol) Interactive image
Interactive image
ChemSpider 62426 YesY
PubChem 69213
Properties
C6H4O4
Molar mass 140.09 g·mol−1
Melting point 212.5 °C (414.5 °F; 485.6 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with formula C
6
H
4
O
4
, formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid[1] with planar molecules[2] that exhibits ferroelectric properties.[3]

The compound is a weak acid: one or both hydroxyls can lose a proton to yield the anions C
6
H
3
O
4
(pKa1 = 2.95) and C
6
H
2
O2−
4
(pKa2 = 4.87), respectively. The latter forms a variety of metal complexes, functioning as a binucleating ligand.[4]

The compound has been identified as partly responsible for the color of aged cellulosic materials.[5]

See also

References

  1. 1 2 Onkar Singh, Aran Kumar, and Karan Singh (2012), "Polymeric complexes of 2,5-Dihydroxy-1,4-benzoquinone with some Lanthanides". International Journal of Scientific and Research Publications, volume 2, issue 9 ISSN 2250-3153
  2. Semmingsen, Dag "The crystal and molecular structure of 2,5-dihydroxy-1,4-benzoquinone at -162°C" Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 1977, volume B31, 11-14.
  3. Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori "Hydrogen-bonded donor-acceptor compounds for organic ferroelectric materials" Chemical Communications 2007, 2321-2329. doi:10.1039/B617881B
  4. Kitagawa, Susumu; Kawata, Satoshi "Coordination compounds of 1,4-dihydroxybenzoquinone and its homologues. Structures and properties" Coordination Chemistry Reviews 2002, volume 224, 11-34. doi:10.1016/S0010-8545(01)00369-1
  5. Hosoya, Takashi; French, Alfred D.; Rosenau, Thomas "Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a key chromophore in aged cellulosics" Mini-Reviews in Organic Chemistry 2013, volume 10, pp. 309-315.


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