Ethylene dione, with a chemical formula $\ce{C2O2}$ and an IUPAC name of ethene-1,2-dione, is an oxocarbon.


The Wikipedia page says:

The existence of $\ce{OCCO}$ was first suggested in 1913. However, despite its deceptively "simple" structure, for over a century the compound had eluded all attempts to synthesize and observe it. Such elusive nature had earned $\ce{OCCO}$ the reputation of a hypothetical compound and a mysterious, "exceedingly coy molecule".

I cannot understand what the rest of the article is telling me. So, why is ethylene dione unstable?

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    $\begingroup$ Well, being a dimer of CO doesn't do it any good. $\endgroup$ – Mithoron Jun 26 '17 at 14:04

The strength of a bond can be determined by the amount of electron density accumulated in the bonding region. A general rule is that the more electron density, the stronger the bond. This is due to a stronger attraction of the nuclei to the bonding electrons. (Of course, if there is too much, it may in turn become overall repulsive, like in the fluorine molecule.)

With an oxygen atom attached to each carbon, there is a strong inductive effect pulling electrons away from the carbon-carbon bonding region of the ethylene dione molecule. Thus, the strength of the carbon-carbon double bond in ethylene dione is greatly reduced, resulting in its instability. This is one plausible explanation.


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