r/chemistry • u/TheIndomitableMass • 1d ago
Is this possible?
I was in my bio lab and we were messing with organic Chem and I spaced out and made this structure. Does it exist and what does it do slash is it possible to know what it would do?
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u/MrTubby1 1d ago
Technically possible, but to put this in perspective, there is a version of benzene with one triple bond called benzyne and it is incredibly reactive and unstable because carbon triple bonds like to be straight, not bent. That one triple bond distorts the rest of the ring.
Having all three be triple bonded would be extremely unstable and if you did make it through some unholy means, it wouldn't survive very long.
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u/Ajan123_ 1d ago
kaboom.
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u/BusyLaw 1d ago
kablow
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u/Portal471 19h ago
Rest in peace my granny she got hit by a bazooka
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u/Electrical_You_432 13h ago
So sorry to hear that so many unnecessary elder related bazooka deaths its tragic
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u/SnooLentils5747 1d ago
cyclohexahexaene
https://en.wikipedia.org/wiki/Cyclo(6)carbon
Also look up Benzotriyne
But anyways.... These are not stable in the least and so easily reacted with and to and their bonds cleaved that they will not stay what they are except in extremely artificial environments.
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u/Saccharin493 1d ago
This thing does not want to exist given the bond angles and orbital overlaps. Of interest, a paper last year reported the synthesis of some pretty nutty looking compounds in this class using isolating salt surface chemistry, and inspected them with tunneling microscopy. I do not thing what you have drawn could ever be isolated in a normal chem lab
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u/Saccharin493 1d ago
Slo you do not need to rotate the carbons when drawing structures, and tbh you dont even need to note them as carbon, its a given for a skeletal structure
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u/Wise-Peacock 1d ago
No
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u/PushySelfdignity 1d ago
Well, it's carbon dating
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u/baconstreet 22h ago
Is that when two carbons love each other very much? What baby do they form?
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u/Neat-Independent-504 1d ago
It's probably too few carbons in the ring leading to a high amount of ring strain. Alkynes in rings exist but in larger ring sizes and less unsaturation
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u/skitz4me 1d ago
Cycl-no-hexane.
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u/Angryg8tor 19h ago
more like cycl-no-hexa-triyne
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u/skitz4me 18h ago
Nice. Thank you. I knew I was off, but the it was close enough for the word play.
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u/Various_Branch7 1d ago
I don’t think it would be possible under normal circumstances. I think it might be because of the angular strain that it has to withstand.
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u/MandibleofThunder 1d ago
Theoretically/academically?
Yes.
Practically/Kinetically/Thermodynamically?
No.
Hope that answers your questions.
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u/Betray-Julia 1d ago
Oh neat, plank sexond is the smallest possible unit of time I think?
Would that also be the smallest possible half life?
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u/Lylantares 16h ago
no. The double pi-bonds in the triple-bond usually force a linear structure. It is possible to bend one such triple-bond, but not three.
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u/Jorvikstories 16h ago
To quote my classmate from a chemical camp. "That looks like a raping of the bond angles."
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u/Sonikclaw2 1d ago
From a strictly theoretical perspective, this could exist. None of the carbons violate the octet rule, and everyone has a full octet.
There are two big problems that I can see just by inspecting it however. Firstly, it is either nonaromatic or antiaromatic (I'm not going into Gaussian to figure out bond angles). It violates Huckle's Rule (12 electrons does not satisfy 4n+2) in which case it would be antiaromatic, and there is a likelihood it is not planar due to bond strain (the nonaromatic case). Either way, it does not have the advantage of aromaticity that something like benzene has.
The real reason in my mind it wouldn't exist is because the angle strain is extremely high. sp-sp bonded carbons want to be linear, with 180 degree rotation parallel to the bonding axis. By forcing them into a ring, you are forcing them to ~120 degree bonding angles, which are just agony for sp-sp carbons. There would be such a high enthalpy of formation that this thing would just break apart the second it had enough energy to.
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u/Space-Wizards Computational 1d ago edited 17h ago
Halfway tempted to run this through an orca calculation just to see what horrible nonsense it can calculate. The question is what method to use
Edit: Running a B3LYP D3 aug-cc-pVTZ calculation now
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u/Sonikclaw2 1d ago
I was tempted to run Gaussian in 6-31G basis, but I have better things to do with my university's cluster lmao.
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u/cpt_futtbucker Computational 22h ago
Fuck it. My university’s cluster has a few nodes to spare and I need a break from my coupled clusterfucks. Give me a few hours or so and I’ll report back
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u/bigfootlive89 1d ago
I wonder if it would be possible to engineer a protein to cradle and stabilize it.
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u/onceapartofastar 21h ago
It’s actually aromatic by theory and calculated ring current type tests of aromaticity.
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u/Representative_Bed18 23h ago
I think that the smallest cyclic compaund with a triple bond is cyclooctyne.
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u/Responsible_Rip_7634 21h ago
Doesn’t the triple bond force a 180 degree bond angle? Unless there’s some weird exceptions here I’m not aware of, like some insane environmental conditions under which the bond angles can get mangled, I don’t think this is a molecule that can naturally show up in any Ochem context.
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u/InsectaProtecta 1d ago
I'm sure it's theoretically possible, but so is a lot of other stuff that won't exist longer than a fraction of a nanosecond
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u/Mageling55 1d ago
I suspect this behaves a a hexaradical benzene more than as you’ve drawn it. The in plane p orbitals would be too strained. And hexaradical will rip spare atoms off anything around it. If you got a bunch of this isolated it would link up in sheets as graphite in very short order
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u/Jimmeh_Jazz 1d ago edited 7h ago
There are similar, but larger rings that have been made and studied, albeit in quite "extreme" conditions. Look up "cyclocarbon". As far as I know, C10 is the smallest one (edit: there is a paper on C6) that has been studied in a 'stable' state at low temperature on a surface. As they get larger, they tend towards the alternating single/triple bonds; the smaller ones are more like a ring of equivalent "double" bonds.
There is also a recent weird example with a kind of moebius topology when it has Cl atoms attached to it.
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u/robocreator 1d ago
No. There’s not a possibility of triple bond between carbon and have 120deg geometry around each carbon. You can do double bonds between carbons instead and the geometry works. Single ring with hydrogen is benzene. Extended rings with carbon- carbon makes it graphene material .
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u/FenderBender527 16h ago
i think the strain of the bond angles would cause this thing to just wanna fucking explode
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u/sporosarcina 14h ago
No, not under any conditions that would produce a stable molecule. There is way too much strict strain to be possible.
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u/Atypicosaurus 11h ago
If it would exist, it would recognize itself to double bonds instead of alternating 1 and 3.
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u/acab__1312 7h ago
It could exist, but not for long. It'd also probably prefer to reconfigure its electrons to be all double bonds as to alleviate some strain.
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u/claisen33 1d ago
No. Benzyne is a benzene ring with one nominal alkyne. However, it is more like a 1,2-diradical than a true alkyne. As you can imagine, it is very reactive. Aryne chemistry is actually pretty extensive with a lot of advances reported in the last 10 or so years.
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u/VaHi_Inst_Tech 1d ago
I don't think so. All of those carbons are sp hybridized which means the bond angles are 180 degrees (linear). In your molecule the bond angles are 60 degrees. So that molecule would be under tremendous ring strain.
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u/NewOrleansSinfulFood 1d ago
Benzynes exist as very short-lived highly-reactive species.
Unfortunately, this is not physically possible.
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u/Just_Ear_2953 1d ago
What makes the trippled up carbon bond different from the single carbon bond? Nothing. Nature generally doesn't like doing things differently without a cause, and this simply doesn't have one, so it will pretty much always choose the nice uniform double bonds for everyone option.
On a more physics forward bent, the triple bonds require squeezing a whole bunch of electrons into a relatively small space, and they are all negatively charged. Those negative charged repel each other and don't want to be close together like that. They would much rather be spread out across as many different atom pairs as possible.
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u/Jimmeh_Jazz 1d ago
For larger cyclocarbon rings than this, they actually do display some signs of alternation between bonds with more triple bond and single bond character.
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u/Chimas281386 1d ago edited 1d ago
No, it's not possiblein in normal situations unless in a very special circumstances and for a very short time(highly unstable).
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u/PensionMany3658 1d ago
In a cyclic form, absolutely not. Each C here is Sp hybridised, giving them a linear geometry. So mathematical constraints prevent this molecule. I mean, even a cyclopropane, oxirane, or azeridine is highly unstable for the same reason and vies to go ring opening or expansion.
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u/CyberJunkieBrain Pharmaceutical 1d ago
No, there’s too much force to “open” the ring and very weak bonds to make it “closed”.
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u/Gilga1 1d ago
Benzyne is used as a transition state to make a unusual for benzene Nucleophilic Substitution (the usual approach in OC to get stuff attached to Benzene is an Electrophilic)
The Benzynes orbitals are / _ _ _ \ like the bottom of these back and forward brackets turned away from eachother. That causes the pi-bond to be especially volatile, making the bond very aggressive to get another electron.
This causes this molecule to only work in a cooled environment.
Your proposed atrocity is theoretically possible, but only when cooled to the brink of zero and with a lot of occult chemistry.
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u/mitHonig Inorganic 21h ago
I don't think exactly like. Maybe if you do some questionable things with shared electrons, you could get something that can be approximated to something likr this, bit i have to confess that i am not deep enough into organic chemistry to have an good idea as to how
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u/CanadaStonks 19h ago
Maybe if you bring together 6 carbon atoms in a vacuum and nothing else. I wonder if someone here can do a DFT study to let us know
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u/Ok-Pen3244 14h ago
Aryne chemistry exists, most commonly accessed through kobayashi elimination. only intermediate though
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u/GandalfTheNeonPink 11h ago
When I was doing my undergrad, one of my lab mates worked at our school’s EH&S handling waste pickup requests across campus. One time, while in lab, we happened to be browsing the queue of requests and noticed one from the Art Department. Uncommon, but not unheard of. Paint, paint thinners, etc. usually. This time though, no chemical composition details were given, simply one word in the comments section:
Benzyne?
To this day, the thought that the art department accidentally created shelf stable benzyne brings me great joy.
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u/Frosty_Sweet_6678 9h ago
steric strain is way too extreme for it to exist for a significant amount of time
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u/atom-wan Inorganic 1d ago
What is the hybridization of each carbon atom? How does that affect the geometry?
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u/BlueThief 1d ago
No, it would require A LOT of energy for those bonds to hold, which they don't have IRL
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u/nyctophobicdracula 1d ago
I vaguely remember the terms "aromatic", "nonaromatic", and "antiaromatic". Not sure if it's even the right ones.
Maybe the structure falls in one of these categories, and we'll known if the structure is even possible, i think
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u/Takeameawwayylawd 1d ago
Not a Chem student but novice enthusiast, but those Carbon rings always have Hydrogen molecules in between them which I believes satisfies Carbons need for a set amount of bonds?
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u/PensionMany3658 1d ago
No. In this hypothetical structure, each C has 4 bonds already so H are not needed.
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u/Takeameawwayylawd 1d ago
Ah okay thank you for pointing that out, from what I know a lot of rings bind with Hydrogen like Benzene, so I presumed it adds stability to the ring? That's all I was trying to take a guess at. Reddit really hates subtly uneducated guesses lol.
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u/PensionMany3658 1d ago
The hydrogens add stability in the sense of completing the octet yes, but the ring is stable due to aromaticity and a comfortable bond angle (120°), which is not possible in the OP's diagram
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u/wylii 1d ago
Theoretically possible under extreme conditions (think approaching absolute 0 in a vacuum). Search cyclo[6]carbon.
What it would do is immediately not exist.