I Made Cubane First
Vložit
- čas přidán 28. 05. 2024
- Check out @ExtractionsAndIre ! It's all in good fun and we talked about it before. Definitely watch his series for the spider infested shed synthesis of cubane.
Thanks to @That_Chemist for making the bromination mechanism and helping with some others
3D Molecule animation of Diels-Alder adduct made by @reformlabs1050
Support my channel with patreon:
/ chemiolis
Cyclopentanone synthesis: www.orgsyn.org/demo.aspx?prep=...
Literature I used for all steps (except UV): doi.org/10.1016/j.bmcl.2013.1...
Literature I used for UV-step and onward: doi.org/10.1039/D3OB00231D
--------------------------------------------------------------
0:00 - 0:52 Intro
0:52 - 5:23 Cyclopentanone
5:23 - 9:11 Cyclopentanone ethylene ketal
9:11 - 15:05 Tribromo
15:05 - 18:39 Diels-Alder adduct
18:39 - 23:11 Deprotection to diketone
23:11 - 25:27 Photoreaction to decahedron
25:27 - 29:53 Cubane dicarboxylic acid
29:53 - 33:32 Cubane dicarboxylate methyl ester
------------------------------------------------------------- - Věda a technologie
NMR analysis of my Cubane and some precursors can be seen in this video:
czcams.com/video/m08fbrhQqnE/video.html
uWu
Bro casually made cubane and made one quick video about it 💀💀 poor Tom
Bro is the Patrick Bateman of chemistry💀
I don't know about a "quick" video, It's over half an hour long. But bro really did drop the b*mb on us, like seriously. Lol!
@@BackYardScience2000 but Tom has like 12 video's of an hour long spreading 3 or 4 years and he still doesn't have it lmao
Advance tinkering beat them both, look it up.
@@swampmonkey420 well, not exactly
bro
those last few words, savage
at least he didn't blow it up on a can of strongbow :)
Nobody has made prismane yet! It's like the white phosphorus but carbon
force him to do yellow chemistry NOW
To be completely fair to E&F, Toms been trying to do this out of a garage using hacked together equipment, which is the appeal of his series. This appears to be under a proper lab environment, so while I appreciate the time and effort that went in to this impressive synthesis, I’m still very much looking forwards to seeing Tom succeed!
Exactly. Everyone's neglecting to take into account that the whole point of Toms project is to do as much of it with hardware store ingredients as possible.
@@EddieTheH Still, if I was tom I would feel a little scooped. I like tom's series much better and making it from hardware store ingredients is much more impressive. It must not feel good to see this video though, if I were him I would be a little upset.
@@mr.m0lam0la Yeah, it's gotta suck when everyone else jumps on your mission!
Tom doing it using only hardware store chemicals in his garage like a crackhead/meth head is definitely important context for his series. I'm happy to see Chemiolis pull this off with such great yields, but I'm most definitely on Tom's team. He's put his heart into this project and has even shown us all the different times he goofed.
"FUGK YELLOW" -Ex&F Squad
@@joeflosion Yeah, that's one of the reasons I'm sticking up for Tom too. You can learn so much from seeing the mistakes. When you see a prep done perfectly and everything goes to plan, then great, you've seen the ideal. But when you see mistakes made and how they're corrected or worked around, there's tons more useful information.
It's not about the Cubane, it's about the tars we made along the way.
Just what I was thinking 🤣
RIP Australian thesis guy🙏
I hope he can cope his loss..
@@laurahaaima1436 i feel sorry for him
@laurahaaima1436 He’ll probably just turn to meth after this one. At least he could make his own! 😂
@@Sniperboy5551 he'd get caught because the neighbors hear him cursing about fuckin YELLOW METH
Yes, but had we seen the beautiful Aussie wildlife checking in to see who can eat whom? No. Did the author bitch and moan anout his thesis? Also, no. 1/10 for drama. If I want to learn chemistry, I'd rather read a textbook.
BIG DAY FOR THE CUBANE COMMUNITY
LGBTQIAC+ community? 🤣
This is the greatest day ever for the nation of Cuba
@@Sniperboy5551??
heh. nice.
Cubane explosives are intriguing but now I really understand the note in the wiki article stating "[a]lthough octanitrocubane is predicted to be one of the most effective explosives, the difficulty of its synthesis inhibits practical use."
This guy will make it.
making the cubane isnt hard.
Its getting 8 nitro groups onto it.
getting 8 nitro groups onto anything is a difficult challenge.
It's not even predicted to be one of the most effective explossives, iirc is way way too sensitive
Yeah, when i read that photoreaction step alone is usually done in scales of "3 grams of reagent per 1 litre of solvent, and let it cook under a lamp for a week" i understood that cubane as explosive wouldn't take off. Simply too little product for such setup, and this isn't even some nuclear shit where acquiring stuff by micrograms was acceptable at the start.
@user-bb4ev6ut8i It’s very impractical with our current methods, but you never know if they’ll find an easier route in the future.
Tom will be mad! :D Finally cubane has been synthesized in a home lab. Now octanitrocubane has to be made.
wouldn’t call it a home lab
This guy's stuff is way more high tech than toms
@@Slavicplayer251 I'm at home, in my lab
@@Chemiolis thats what i call it my "coom cave"
Hey man, tbf, the point of Tom's videos are to make it using *mostly* hardware store chemicals. He may have gotten completely scooped here, but I'll always take my Cubane rat infested meth lab style over ligma adritch sigma male style
Organic chemist here - especially with how opaque your photoreaction got, if you decide to run it again, you could probably get a better yield by running several smaller reactions in parallel. Your conversion in that step will be limited by how far your light can penetrate the solution
Doing it in flow using like 15-20m of 1/16" FEP tubing, even in recycling topology is an obvious choice for improvement there
Yes 100%. I believe that the light only really penetrates in maybe 1-2 cm until it becomes very ineffective. So yes more surface area by doing smaller runs is great, flow would be ideal tbh
Obviously you know about 10,000x more about the issue than me, but do we have good reason to believe that the light can't penetrate given that it's out of the visible spectrum? Or is it just that it's black cuz it's producing a ton of random side products that are absorbing (collectively) light from a bunch of wavelengths?
@Rone it's more so that the specific wavelength(s) required to make the reaction work are only really present near the surface of the glass. Assuming that the glass doesn't absorb the wavelength you want, other molecules can absorb and/or transmit the wavelength(s) of light that drive the reaction. This leads to low conversion and the formation of side products. It's not that light doesn't reach the molecules, it's just the molecules in the inner parts of the flask don't get exposed to the wavelengths required to do the desired reaction. At least that's my understanding of it
Not an organic chemist here, but just a curious person with an interest in science/chemistry in general. Would it produce a better yield if he were to flow the material through a borosilicate glass capillary tube with said tube being illuminated with the UV LED lights? I'm also wondering if he could make a box with some high-quality mirrors to help reflect the UV rays back onto the tube to increase the reaction?
Now I want to see you do this in a hot shed with hardware store materials. Bonus points if the shed happens to be in Australia.
I would rather see Tom do that lol.
While also working on a physics PhD thesis.
@@JaxMerrick 😂😂😂😂😂😂😂
Tom & Chemiolis...
I can picture your smug face when you say: "this is a yield of 87%... this is higher than the literature :)"
Bro even I get really excited by the words "which is higher than the literature".
When my yield is higher than literature, especially for very common reactions, I always assume there are impurities or solvent and check with NMR what it is. It's impurities most of the time.
To be fair, Extractions&Ire does many projects and this one is done with very long pauses between steps - he also attemps this with amateur-style chemistry approach, using try/fail methods, makeshift apparatuses (apparati ?).
Once you have proper training and can follow the papers smoothly you get there much faster (learned the hard way myself - the backround knowlege and practice are extremely important).
yeah tom’s working with what any average person with an internet access could do were as old mate here is using high purity commercial chemicals and with the proper equipment
I feel like Tom does have the proper training and background, but just not the time nor this type of setup. He was/is also doing his Phd at the same time.
One of the best chem advice I have ever heard
@@gielb2001 Exactly. He's working out of a shed trying to do it with hardware store chemicals while also being busy writing his thesis, completely different situation. I'm excited to see Tom do it :)
I appreciate the "Nightmare" completionust run that E&F is doing a bit more. But an "I'm Too Young To Die" speedrun is fun too. ;)
I think this is a very good demonstration on how better equipment helps to do chemistry. I would say that both Tom and you are excelent chemists, but the UV lamps, quality reagents, precise work on the destilation under vacc, inert atmo and stuff do really help. I of course see the big work put in the synth by you, but still, the elegance is clear. Keep this work up, greetings from Czechia.
helps to know what a resistor is and how to drive an LED lol
@@vevenaneathna The lighting setup used here is the much easier setup that's been discovered since Tom's big troubles, using a wavelength of light that's much more achievable to generate and get through glass, no crazy custom electronic setups necessary!
When are you guys reforming czechoslovakia?
@@antonh1159 yo I would say that we are not going to reform it any time soon. We are very close to eachother even without the connection anyways so its chill as it is. It would be cool for sure tho
@@ingensvidcz5390 Two neighbooring countries being friendly in europe? Thats rare and quite cool
The key is to keep the spiders and snakes from contaminating your chemistry
Very well done. I'm a Ph.D. student in bioorganic chem/chem bio and it's immediately apparent that you're an excellent synthetic chemist. You know all the tricks and have impeccable technique. You've also accounted for all mechanistic ideas/issues. Masterful molecular control.
Sick work 👏 BTW, 25:47 I think the mechanism is a "quasi Favorskii" only which starts with hydroxide attack on the ketone directly, after which a 1,2 alkyl shift displaces the halogen at the alpha-carbon. The classical mechanism is disfavored because the ketone is not enolizable (anti-Bredt's rule) and the cyclopropanone intermediate would be highly strained.
Yeah that's what I thought too.
Nice.
Exactly my thoughts
As a note: I work with photochemistry a lot, and that scale of reaction is super hard to predict. You’re dealing with complex and changing extinction coefficients and power densities, and I find that even scaling up from 2 mL of solvent to 4 mL (using two 135 W lamps) can prevent reactions from happening or slow them wayyyyy down. Especially if the mixture darkens like that, the reaction can be self quenching. Often you just need more power or shorter wavelength light, or you can leave it for a long time. High powered lights also get hot quickly so I have a fan that cools all my reactions. Adding a reflector like foil around the vessel could have helped too.
Everyone saying rip Tom , like Tom doesn’t make a separate style of series entirely, great to see this done in one episode. But it misses the charm of Tom’s silly backyard shit.
Extractions&ire:
*Makes cubane 3 years and still not even 1 cubane molecule was produced*
Chemiolis:
Fine I will do it by myself
The premise was different so it's ok - chemiolis didn't fuck around with reptile lights and selfmade dioxane and hot himself the good shit right away :)
@@kpunkt98 but also Chemiolis made way better yields and yellow color appeared only at very end
@@unpopulardude1188
But you’ve missed the point of what Tom is doing. Store bought chemicals.
I bet this still took Chemiolis well over a month to do this one
We all can if we throw enough money at it, that wasn't Tom's goal.
But did you use hardware store chemicals?
and did he do it in a hot as fuck australian shed with spiders and lizards who aren't supposed to be in here? fuck me
"Well shit." - Tom (probably)
That step with the Dean Stark @5:40 was magical, with the constant ravaging and rebuilding of the molecule all in one reaction.
Rest in Peace Tom for missing the chance. Also would love to see you making the actual cubane
This is an incredible display of skill, even a noob like me can see that. As many others have pointed out, this is FAR more professional than E&F’s approach. That doesnt take away ANY credit from either party though. Both have their own goals and criteria, external influences, etc. All good knowledge to impart on the world.
Yeah E&F is trying to make it in a crack shack (he has a degree in physics anyways) while this guy is like let's be sane
Well done! And I’m sure Tom is not upset at all…. More like furious haha. Great work as always though.
Tom is using different materials, stuff that’s commonly found in hardware stores while this video used actual reagents
@@hx5525 This channel cheated and used chemicals?!
A Bloody Outrage!
@@fukpoeslaw3613 I know right!
I’m calm……… I’m calm,….,,…..,..,,,,,,
@@ExtractionsAndIre I noticed Chemiolis did put some extra effort in preventing oxidation with nitrogen blankets and such. That has been my theory as to why you have had such a hard time.
I love that you showed and explained the reaction mechanisms involved in each step, something rarely seen in other chemistry channels, amazing work!
You beat the Aussie crackhouse of infernal yellow to it. 😁
Congrats! 😊👍
You know what they say: "The (Aussie crack)House Always Wins"
things seem to be heating up in the Cubane synthesis community part of youtube
and I am all for it this is awesome stuff
Your showing of all steps and reactions is amazing and very interesting to watch!
His cubane synth is far harder than yours since he's doing it the NurdRage way (OTC chems only). It somewhat trivializes the challenge if you just Sigma Aldrich and Schlenk line it. Also I think you were beaten by Advanced Tinkering
Advanced Tinkering made Octosilocubane (Silicon cube instead of carbons) so that may or may not count?
you do realize that silicon is a completely different element from carbon, right?
6:37, Ah, that brings back memories. there was a grad student in my senior year research group that was using that protecting group reaction in a synthesis of bottle-brush polymers. One of the few presentations I went to, but worthwhile.
This is basically brute forcing the reactions. I love it
You are honestly a top notch chemist!! I like how you give so much care and thought to each step
Well congratulations! But also I'm peeved with you for swooping in and beating Tom. I think I was more emotionally invested in that series of his than I thought lol!
No for real, good on you. I know I'll still be excited when E&I does it from 'chemicals from the hardware store'!
Congrats on making the cubane! Some good work and a lot of great chemistry explanation
This guy has talent, but Tom's level of awesomeness cannot be beaten 💙
Dunno about that, looks like a pretty decisive beating in organic chemistry at least
A friend of mine who made cubane in the 70s and then nitrated it for her doctoral thesis in energetics is frowning at you right now.
I absolutely pive that this molecule has brought together all these people. Who would have thought cubane would have a whole CZcams trend lmao
I really love the gentle ribbing done between people here on ChemTube. And I super enjoyed the detailed explanations behind the reactions! I love the synthesis and understanding what's going on behind the chemistry.
I absolutely love the Organic Chemistry community here on CZcams. We are seeing such a advancement in independent work quality due to this awesome community. I just enjoy science and love watching things as they unfold. Its not like i do chemistry in my everyday life. (I loved doing lab work when i took classes) but it goes to show that the content you all make is enjoyable & even beneficial to many different kinds of people. Its awesome this type of content is available. There could be many different aspects this all could be beneficial in different ways. Keep up the great work 👍🏻
I just found your channel, and I love this content! Incredibly professional, and very cool
that was mad cool, id love to see cubane next!
Congratulations!! Seeing this makes me want to do more bench top chemistry. I very much like the large scale approach.
Ok now I just finished the video. Everything cool but... TLC as the sole proof of purity and identity? Can you do NMR or IR? I think the final product deserves further characterization
Haha I can't believe you've done this!
I know nothing about chemistry but I'm enthralled by the cubane series. Most of this video went over my head but it looks like impressive work. Congratulations!
this was such an awesome synthesis to watch. to get yields so close to, and in some cases surpassing the literature is so impressive, especially given how challenging, and even frightening, some of those steps are 😭
Please make cubylamine for Hamilton Morris :) This would make him very happy.
Alright then 😈
wait what is cubylamine? :O
@@tuxpacific2737 substitued cubane with one amino group - there are many pharmaceuticals that can be altered by using cubane instead of benzene ring - a whole new area of possibilities - things like Cuba-Lumafactor, possible cubylamphetamine etc. etc.
Great work congratulations. Now try with OTC starting materials 😂
The "Cubane-Race arc" as I've come to call it has to be one of the most entertaining things that happened in chemtube.
Congrats!
this is seriously impressive. congratulations.
I'm not sure if it was the way these different reactions were explained, but I feel like I actually made a bit of a breakthrough in my chemistry understanding while watching this video. I couldn't really follow the steps very well, but I started to get this idea of manipulating the bonds strategically by the addition of certain types of stress or reactants. It really made me start to understand how I might predict what a chemical would do in certain situations.
Thank you, truly for this video.
This video is actually GOATed. This shows how organic chemistry is really done and your mechanism explanations and drawings are so good! If I were teaching an org course, I'd want to show this video to my students. Please make actual cubane!!!
Very nice work, I appreciate your new humorous approach to these vids
A small note: Although the photorearrangement is theoretically feasible in the singlet manifold, the triplet pathway is probably the dominant mechanism (that’s why the benzophenone works) :]
Amazing procedure!
but is it yellow?
Both Chemiolis and E&F are awesome, thank you for the explanation of all in between steps, I am studying chemistry and this helps :)
Amazing work
All i want right now is a video that shows you talk all calm and professional, side to side with tom shouting and throwing hands and showing his electronic skills.
Love this good nature "competition" and the fact you sent E&F samples so he can compare. 👍👍
👏👏
An impressive tour de force. Thanks!
This channel just makes me happy
Terrific work! Two thoughts: The sulfuric acid deprotection product turned black during work up probably die to leftover acid concentrated when drying, so perhaps a few more water wash/bicarb wash could have prevented that step’s yield loss; And the uv set up would have worked better if you did it in batches in smaller containers. Round shape flasks does not allow penetration of the uv beyond the first few milimeters of the solution as outer layer benzophenone would have absorbed all the light. Our lab found that flow chemistry works very well for large batch photoreactions.
I would love to see your lab. This is awesome.
With all the yellow chem involved, its a wonder Tom has made it as far as he has. Amazing work, I had no idea this channel existed, but now I do.
So awesome! Really liked the humor :)
wow! amazing video! Your channel is seriously underrated
Hey! Cool stuff, are you planning on doing any (proper) analysis of the stuff? Can't say you made something without some proper spectra ;)
I agree, even Tom has the equipment to check that in his backyard meth lab
You may have Cubane, but Tom will always have my heart. ❤️
What a satisfying synthesis. So much precipitation :o
Pretty slick. Nice job.
I have never taken a chemistry class, and my only exposures to it have been via nilered, an off-topic video from tom, and movies. I don't totally know what is going on, I quite enjoyed this video. Thanks for some very entertaining content!
Super! Thank you very much!
Great video my man kep up the great work
Nice job! There are a few things that can be done to improve the yield and also facilitate purification.
16:51 The way you said simply "most of the crap" instead of "impurities" is very funny to me for some reason :D
Also very impressive work, it was very satisfying to watch
Nice to see photochemistry in action.
Will you try to do some complex aromatic compounds such as helicenes or do some heterocyclic compounds?
Even organometallic chemistry would be very interesting.
love your sense of humor
this is so professionally made
Do it with OTC chemicals only then ill accept it :D
Awesome video! My respect!
Rip Tom
awesome video, would love to see that you make the actual cubane itself!
The problem with the deprotection step is that you used concentrated sulfuric acid. This is a hydrolysis reaction. You NEED water to be present. Use dilute sulfuric acid next time and you will see better results.
well played sir! well played
I don't know why we needed to see cubane chemistry get so much attention but I am happy it does
Decent systhesis but cant be compared to Tom as hes doing it home lab style. Im sure if he used all the correct equipment and proper lab chems like you he would of been able to do it yonks ago. Proving it can be done with OTC chems and home lab equipment is a very different kettle of fish and one he should be applauded for.
I challenge the author to fly to Australia, break into Tom's shed, synthesize cubane, and then escape without being detected. No non-accidental deaths, suit only. Silent Scoop-sassin % speedrun.
the black tar in cubane dicarboxylic reaction can be mainly benzofuran, which you can try to wash dicarboxylate salt with benzene
Really impressed by your ability to recover from yellow chemistry.
holy hell youre gifted. so much blood sweat and tears casually explained away with so few words.... also.... are you telling me the crystals are not perfect cubes? WHAT DA HAILLLEEEE???
24:00 get an UV light Tube and run some PTFE tubing lengthwise around it and
wrap it with aluminum foil to maximize the light usage.
you can let it flow through a metal pipe in a bucket of water to keep it cool.
of course you would need a pump too.
Cool video, everyone is hyped with cubane lately
Congratulations!
Cool synthesis, part of my undergrad research was photochemistry specifically the quenching of a aromatic radical by iodide ions. It was all done in water/ethanol so much more likely to have dissolved oxygen than acetonitrile. We had to remove the oxygen from the sample too however we did it with LN and vacuums, a lot of work but the reaction is super sensitive to oxygen and our professor wanted results he could put into a paper. Good alternative you used to instead of using our method, lot less work and way less expensive for probably the same result if you did it the cryogenic route.
Also highly recommend you test your product to make sure you got what you say you did if you haven't already, hate to see all this work for nothing.
This is an incredible video :D
Quite some lovely yellow chemistry!
what is this. shiny glass, solid background. clean equipment. where's the threat of insect attacks? casual piles of chemicals waiting to be disposed? unfinished garden projects? I'm pretty sure chemistry can't be done under these conditions.
to be fair watching tom do chemistry with scrounged up equipment and stuff he found at a hardware store is the exact reason i love him, thanks for the time but tom can make the cubane im sure.
tom talked about this method and the paper two weeks before this video was posted.
I’m not used to watching CZcams videos that get higher yields than the literature. I think the fact that you really make sure to give everything enough time and take care with the recrystallizations makes a huge difference. (Btw I see a lot of people trash talking you in the comments for having good equipment. As a huge fan of Ex&I I really appreciate that you’ve done this because I think that this could really help Tom finally make cubane.)
22:54 I think the reason you got a low yield with the deprotection step was because of all the recrystallizations