NMR analysis of my Cubane and some precursors can be seen in this video: kzread.info/dash/bejne/n2RsyMSrmLTXnqg.html

@saddish2816

8 ай бұрын

uWu

bro

@TehPwnerer

Жыл бұрын

those last few words, savage

@isocle

Жыл бұрын

at least he didn't blow it up on a can of strongbow :)

@createvideo561

3 ай бұрын

Nobody has made prismane yet! It's like the white phosphorus but carbon

@_TheCollective

Ай бұрын

force him to do yellow chemistry NOW

Bro casually made cubane and made one quick video about it 💀💀 poor Tom

@vatsalparmar5740

Жыл бұрын

Bro is the Patrick Bateman of chemistry💀

@BackYardScience2000

Жыл бұрын

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!

@Julian-oy1kr

Жыл бұрын

@@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

@swampmonkey420

Жыл бұрын

Advance tinkering beat them both, look it up.

@cvspvr

Жыл бұрын

​@@swampmonkey420 well, not exactly

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!

@EddieTheH

Жыл бұрын

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.

@mr.m0lam0la

Жыл бұрын

@@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.

@EddieTheH

Жыл бұрын

@@mr.m0lam0la Yeah, it's gotta suck when everyone else jumps on your mission!

@joeflosion

Жыл бұрын

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

@EddieTheH

Жыл бұрын

@@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.

@Wassermelonenbaum

11 ай бұрын

Just what I was thinking 🤣

RIP Australian thesis guy🙏

@laurahaaima1436

Жыл бұрын

I hope he can cope his loss..

@cvspvr

Жыл бұрын

​@@laurahaaima1436 i feel sorry for him

@Sniperboy5551

Жыл бұрын

@laurahaaima1436 He’ll probably just turn to meth after this one. At least he could make his own! 😂

@snakewithapen5489

Жыл бұрын

@@Sniperboy5551 he'd get caught because the neighbors hear him cursing about fuckin YELLOW METH

@antonmeshcheryakov5068

11 ай бұрын

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

@Sniperboy5551

Жыл бұрын

LGBTQIAC+ community? 🤣

@raffaeledivora9517

Жыл бұрын

This is the greatest day ever for the nation of Cuba

@brrrrrr

Жыл бұрын

​@@Sniperboy5551??

@shipofthesun

Жыл бұрын

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."

@professorkieslichschemlab

Жыл бұрын

This guy will make it.

@fsen1999

Жыл бұрын

making the cubane isnt hard. Its getting 8 nitro groups onto it. getting 8 nitro groups onto anything is a difficult challenge.

@ficolas2

Жыл бұрын

It's not even predicted to be one of the most effective explossives, iirc is way way too sensitive

@quint3ssent1a

Жыл бұрын

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.

@Sniperboy5551

Жыл бұрын

@user-bb4ev6ut8i It’s very impractical with our current methods, but you never know if they’ll find an easier route in the future.

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

@midi5581

Жыл бұрын

Doing it in flow using like 15-20m of 1/16" FEP tubing, even in recycling topology is an obvious choice for improvement there

@platinumwaiter

Жыл бұрын

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

@tsawy6

Жыл бұрын

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?

@platinumwaiter

Жыл бұрын

@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

@amanawolf9166

Жыл бұрын

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?

Tom will be mad! :D Finally cubane has been synthesized in a home lab. Now octanitrocubane has to be made.

@Slavicplayer251

Жыл бұрын

wouldn’t call it a home lab

@RickCollins1993

Жыл бұрын

This guy's stuff is way more high tech than toms

@Chemiolis

Жыл бұрын

@@Slavicplayer251 I'm at home, in my lab

@user88169

Жыл бұрын

​@@Chemiolis thats what i call it my "coom cave"

@zevkurtzman8108

Жыл бұрын

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

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.

@Kraus-

Жыл бұрын

I would rather see Tom do that lol.

@JaxMerrick

Жыл бұрын

While also working on a physics PhD thesis.

@Cruz-tc6df

Жыл бұрын

@@JaxMerrick 😂😂😂😂😂😂😂

@professorkieslichschemlab

Жыл бұрын

Tom & Chemiolis...

I can picture your smug face when you say: "this is a yield of 87%... this is higher than the literature :)"

@alexpotts6520

Жыл бұрын

Bro even I get really excited by the words "which is higher than the literature".

@bejarni7173

Жыл бұрын

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.

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. ;)

The key is to keep the spiders and snakes from contaminating your chemistry

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.

@vevenaneathna

Жыл бұрын

helps to know what a resistor is and how to drive an LED lol

@tsawy6

Жыл бұрын

@@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!

@antonh1159

Жыл бұрын

When are you guys reforming czechoslovakia?

@ingensvidcz5390

Жыл бұрын

@@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

@antonh1159

Жыл бұрын

@@ingensvidcz5390 Two neighbooring countries being friendly in europe? Thats rare and quite cool

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).

@Slavicplayer251

Жыл бұрын

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

@gielb2001

Жыл бұрын

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.

@Ormodius3751

Жыл бұрын

One of the best chem advice I have ever heard

@lulumccoolio3111

11 ай бұрын

@@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 :)

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.

@victordonchenko4837

Жыл бұрын

Yeah that's what I thought too.

@InconspicuousOwl

Жыл бұрын

Nice.

@antonhelsgaun

Жыл бұрын

Exactly my thoughts

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.

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.

Rest in Peace Tom for missing the chance. Also would love to see you making the actual cubane

Extractions&ire: *Makes cubane 3 years and still not even 1 cubane molecule was produced* Chemiolis: Fine I will do it by myself

@kpunkt98

Жыл бұрын

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 :)

@unpopulardude1188

Жыл бұрын

@@kpunkt98 but also Chemiolis made way better yields and yellow color appeared only at very end

@Margarinetaylorgrease

Жыл бұрын

@@unpopulardude1188 But you’ve missed the point of what Tom is doing. Store bought chemicals.

@Sniperboy5551

Жыл бұрын

I bet this still took Chemiolis well over a month to do this one

@Milkex

Жыл бұрын

We all can if we throw enough money at it, that wasn't Tom's goal.

Well done! And I’m sure Tom is not upset at all…. More like furious haha. Great work as always though.

@hx5525

Жыл бұрын

Tom is using different materials, stuff that’s commonly found in hardware stores while this video used actual reagents

@fukpoeslaw3613

Жыл бұрын

@@hx5525 This channel cheated and used chemicals?! A Bloody Outrage!

@hx5525

Жыл бұрын

@@fukpoeslaw3613 I know right!

@ExtractionsAndIre

Жыл бұрын

I’m calm……… I’m calm,….,,…..,..,,,,,,

@mooreanalytical4105

Жыл бұрын

@@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.

You beat the Aussie crackhouse of infernal yellow to it. 😁 Congrats! 😊👍

@bronzecomeshome9517

Жыл бұрын

You know what they say: "The (Aussie crack)House Always Wins"

That step with the Dean Stark @5:40 was magical, with the constant ravaging and rebuilding of the molecule all in one reaction.

"Well shit." - Tom (probably)

This is basically brute forcing the reactions. I love it

things seem to be heating up in the Cubane synthesis community part of youtube and I am all for it this is awesome stuff

I love that you showed and explained the reaction mechanisms involved in each step, something rarely seen in other chemistry channels, amazing work!

But did you use hardware store chemicals?

@tbounds4812

Жыл бұрын

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

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.

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.

@Ornateluna

Жыл бұрын

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

This guy has talent, but Tom's level of awesomeness cannot be beaten 💙

@iNerdier

Жыл бұрын

Dunno about that, looks like a pretty decisive beating in organic chemistry at least

I absolutely pive that this molecule has brought together all these people. Who would have thought cubane would have a whole KZread trend lmao

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!

You may have Cubane, but Tom will always have my heart. ❤️

Please make cubylamine for Hamilton Morris :) This would make him very happy.

@Chemiolis

Жыл бұрын

Alright then 😈

@tuxpacific2737

Жыл бұрын

wait what is cubylamine? :O

@LiborTinka

Жыл бұрын

@@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.

Your showing of all steps and reactions is amazing and very interesting to watch!

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'!

You are honestly a top notch chemist!! I like how you give so much care and thought to each step

Great work congratulations. Now try with OTC starting materials 😂

I absolutely love the Organic Chemistry community here on KZread. 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 👍🏻

Congrats on making the cubane! Some good work and a lot of great chemistry explanation

Congratulations!! Seeing this makes me want to do more bench top chemistry. I very much like the large scale approach.

@niconeuman

Жыл бұрын

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

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.

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 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 😭

that was mad cool, id love to see cubane next!

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!

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.

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.

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) :]

I just found your channel, and I love this content! Incredibly professional, and very cool

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.

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.

Hey! Cool stuff, are you planning on doing any (proper) analysis of the stuff? Can't say you made something without some proper spectra ;)

@Sniperboy5551

Жыл бұрын

I agree, even Tom has the equipment to check that in his backyard meth lab

Rip Tom

this is seriously impressive. congratulations.

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

Both Chemiolis and E&F are awesome, thank you for the explanation of all in between steps, I am studying chemistry and this helps :)

An impressive tour de force. Thanks!

Really impressed by your ability to recover from yellow chemistry.

Amazing work

So awesome! Really liked the humor :)

Do it with OTC chemicals only then ill accept it :D

wow! amazing video! Your channel is seriously underrated

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!!!

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

@Enderdragon91

Жыл бұрын

Advanced Tinkering made Octosilocubane (Silicon cube instead of carbons) so that may or may not count?

@andrewjin6618

Жыл бұрын

you do realize that silicon is a completely different element from carbon, right?

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.

@Smith5783

Жыл бұрын

tom talked about this method and the paper two weeks before this video was posted.

Great video my man kep up the great work

Awesome video! My respect!

Love this good nature "competition" and the fact you sent E&F samples so he can compare. 👍👍 👏👏

What a satisfying synthesis. So much precipitation :o

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.

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!

This channel just makes me happy

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.

Amazing procedure!

awesome video, would love to see that you make the actual cubane itself!

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.

but is it yellow?

Yes, we want cubane, and we won't settle for less than pure cubane

HISTORICAL DAY FOR THE CUBE FANDOM

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???

well played sir! well played

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.

Super! Thank you very much!

I would love to see your lab. This is awesome.

This is an incredible video :D

this is so professionally made

Nice job! There are a few things that can be done to improve the yield and also facilitate purification.

What a big accomplishment!

Pretty slick. Nice job.

Cool video, everyone is hyped with cubane lately

love your sense of humor

Congratulations!

I don't know why we needed to see cubane chemistry get so much attention but I am happy it does

The thing that gets me is that this psycho didn't just beat Tom, he also got a better yield than the people who discovered this route.

@Gamerzsociaty

Жыл бұрын

Technically his final yield was lower than literature however he mentioned he wasn't 100% sure due to conversions with the UV reaction

@anthrazite

Жыл бұрын

Using 5 digits worth of chemicals and lab equipment makes for different conditions than trying to do it with hardware store chemicals in a garden shed

@shitfuckmcgee8611

Жыл бұрын

@@anthrazite I definitely regret the tone of my comment lol I just thought it was funny that Chemiolis was beating literature yields. Tom's success, when it comes, will be a far more significant landmark for home chemistry IMO. In fact, his progress up to this point has been very impressive.

we thought the whole point was getting cubane, but it was all about the friends we made along the way

@zevkurtzman8108

Жыл бұрын

Amen brother

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.