Is the smallest carbon molecule smaller than C20?

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The discussion centers on the existence and stability of small carbon molecules, particularly those smaller than C20. C2 is identified as a molecule that exists but is highly unstable, often reacting quickly with other substances like hydrogen to form more stable compounds such as ethane. The bonding in C2 raises questions about its natural occurrence and stability, with participants debating its geometric configurations and potential resonance stabilization. The conversation also touches on the theoretical existence of C4, which is speculated to have a planar rhombic structure due to its double bonds, though doubts remain about its synthesis and stability. Additionally, tetrahedral N4 is mentioned as a high-energy compound with potential applications as an environmentally-friendly rocket fuel, though it has not yet been synthesized. Overall, the discussion highlights the complexities of carbon molecule stability and the challenges in studying these small compounds.
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Does there/or could there exist a molecule made only of carbon, that is smaller than C20?
 
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Yes. C2 is a molecule Smaller than C2O. Whether it's a naturally occurring one, I'm not sure.
 
Xtensity said:
Yes. C2 is a molecule Smaller than C2O. Whether it's a naturally occurring one, I'm not sure.

As far as I knew the bonding for C2 is not possible, that's why I asked. Maybe I was misinformed. Perhaps its just that it does not occur in nature. How would the bonding work?
 
I think C-C will wander until it picks up some -H for example, to make ethane.
 
Well if that is allowed, geometrically I can imagine C4, formally a square with two acetylenic bonds, or a tetrahedron with two double bonds. Both have very strained bond angles but would they get some resonance stabilisation? Could it be made difficult for them to decay into anything if e.g. in dilute gas*? :confused:

*for the reason below.
 
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C2 is certainly very stable to dissociation and has been characterized completely in the gas phase. However it cannot be filled in bottles as there are other carbon modifications which are even more stable and to which C2 quickly reacts.
 
epenguin said:
Well if that is allowed, geometrically I can imagine C4, formally a square with two acetylenic bonds, or a tetrahedron with two double bonds.

Neither, C4 (if it exists) is planar and rhombic (since the double-bonds are shorter). I'm doubtful it's been synthesized, and I'm doubtful of its stability. There are some recent theoretical studies of its radical ions, though.

There's tetrahedral N4, which I'm a big fan of. Never synthesized either, but I know that one's supposed to be somewhat stable (energetic barrier to decomposition of around 10 kcal/mol or something). It's a very high-energy compound (something like 50 MJ/kg IIRC). It's been proposed as an environmentally-friendly rocket fuel. If someone could come up with some way of making it.
 

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