Cyclopentanepentone

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Cyclopentanepentone
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Names
Systematic IUPAC name
Cyclopentane-1,2,3,4,5-pentone [1]
Other names
Leuconic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C5O5/c6-1-2(7)4(9)5(10)3(1)8 X mark.svgN
    Key: YVVXMBHAKNKELS-UHFFFAOYSA-N X mark.svgN
  • O=C1C(=O)C(=O)C(=O)C1=O
Properties
C5O5
Molar mass 140.050 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Cyclopentanepentone, also known as leuconic acid, is a hypothetical organic compound with formula C5O5, the fivefold ketone of cyclopentane. It would be an oxide of carbon (an oxocarbon), indeed a pentamer of carbon monoxide.

Contents

As of 2000, the compound had yet to be synthesized in bulk, but there have been reports of trace synthesis. [2] [3] [4]

Cyclopentanepentone can be viewed as the neutral counterpart of the croconate anion C
5
O2−
5
.

The compound referred to in the literature and trade as "cyclopentanepentone pentahydrate" (C5O5·5H2O) is probably decahydroxycyclopentane (C5(OH)10). [3] [5]

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([ON=NO]2−), or to any ionic compound that contains it. In organic chemistry, it may also refer to the group −O−N=N−O−, or any organic compound with the generic formula R1−O−N=N−O−R2, where R1 and R2 are organic groups. Such compounds can be viewed as salts and esters of respectively hyponitrous acid H
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References

  1. "CID 12305030 - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. Rubin, M. B.; Gleiter, R. (2000). "The Chemistry of Vicinal Polycarbonyl Compounds". Chemical Reviews. 100 (3): 1121–64. doi:10.1021/cr960079j. PMID   11749259.
  3. 1 2 Seitz, G.; Imming, P. (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.
  4. Schröder, D.; Schwarz, H.; Dua, S.; Blanksby, S. J.; Bowie, J. H. (1999). "Mass spectrometric studies of the oxocarbons CnOn (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. Bibcode:1999IJMSp.188...17S. doi:10.1016/S1387-3806(98)14208-2.
  5. Person, W. B.; Williams, D. G. (1957). "Infrared Spectra and the Structure of Leuconic Acid and Triquinoyl". Journal of Physical Chemistry. 61 (7): 1017–1018. doi:10.1021/j150553a047.

See also