Deltic acid

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Deltic acid
Names
Preferred IUPAC name
2,3-Dihydroxycycloprop-2-en-1-one
Other names
  • Deltic acid
  • Dihydroxycyclopropenone
  • Trianglic acid
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1/C3H2O3/c4-1-2(5)3(1)6/h4-5H
    Key: SPXGBDTUWODGLI-UHFFFAOYAW
  • O=C1C(O)=C1O
Properties
H2C3O3
Molar mass 86.046 g·mol−1
Appearance White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Deltic acid (also known as dihydroxycyclopropenone or trianglic acid) is a chemical substance with the chemical formula C3O(OH)2. It can be viewed as a ketone and double enol of cyclopropene. At room temperature, it is a stable white solid, soluble in diethyl ether, that decomposes (sometimes explosively) between 140 °C and 180 °C, and reacts slowly with water.[1]

Derivatives

Deltate and salts

Deltic acid is considered an

anion
, C3O2−3.

The first deltate salts (of lithium and potassium) were described in 1976, also by Eggerding and West. Lithium deltate Li2C3O3 is a water-soluble white solid.[1] Like the other cyclic dianions with formula (CO)2−
n, the deltate anion has a pronounced aromatic character which contributes to its relative stability.[1]

Analogs

An analog of the deltate anion can be obtained by replacing the three oxygen atoms (=O or −O−) by cyanoimino groups (=N−C≡N or −N=C=N−) to yield the symmetric anion C3(NCN)2−3.[2] Replacement of the three oxygen atoms by dicyanomethylene (=C(CN)2) provides an oxidizing species that is readily reduced to a stable radical anion and dianion.[3]

Synthesis

Deltic acid was originally obtained by

UV light, the disilyl compound decarbonylates. Decomposition of the latter by butanol yielded deltic acid.[4]

The acid can also be prepared by reaction of silver squarate and trimethylsilyl chloride.[1][5]

The deltate anion has also been obtained by direct

coordination compound yielding a deltate anion bound to two uranium atoms.[6]

See also

References

  1. ^
    doi:10.1021/ja00428a043
    .
  2. doi:10.2116/analscix.22.x239
    .
  3. doi:10.1021/ja00418a050
    .
  4. doi:10.1021/ja00834a047
    .
  5. doi:10.1016/S0040-4039(00)72653-0
    .
  6. S2CID 6657874
    .
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