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What if you mix the most based superbase with the most cringe Superacid?

“Yo bro, do you want a superbase?” “NaH, bro.”

This video is based.

An increase in pK_BH of 0.5 means that a base is10^0.5 = 3.16 times stronger, not 5 times.

The Pandora's Phosphazene deserves the mythical SS tier.

I just remembered I have a “fun” chemistry story. So I’m in grade 7, and my small private school is doing a science fair. Dry ice was a popular ingredient in science fair projects as it makes cool (literally) vapours. No one of the students in the grade 8 class was using dry ice to make bubbles with soap and warm water. The issues started when lunch came around and he started messing around with the dry ice in more explosive ways. By adding a chunk of dry ice to a plastic bottle, pouring in very hot water, and quickly sealing it, you get a grenade. Several bottles were filled and then thrown, exploding several seconds afterwards. Then this guy filled one of those small yogurt bottles with dry ice and hot water. He threw it, it hit the ground. And nothing. Everyone watching including myself waited for about 10 seconds as nothing happened. Then he walked towards this bottle and picks it up. That agitation was enough to get the pressurized bottle to go kablewy. So did his hand. He ran to the bathroom dripping blood and EMS was called. After about a month or two he came back into school. With a 5 inch scar running from his wrist to his palm between his thumb and pointer finger. He had broken probably half the bones in his hand, and almost ripped his thumb clean off. Dry ice was promptly banned from science fair projects. Moral of the story. Don’t play with explosives if you don’t have ppe and proper protocols

Sodium Hydroxide ain't the weirdest basic salt used in german food. Ammonium Carbonate is used in cookies and used to be soured from burning deeer antlers.

The Pandora's Phosphazene one is just funny to my brain, like yeah just slap moee phosphazene groups together, and why not make those pyrrolidine rings while you're at it... Someone out there seems to have followed this train of thought and gone off to do theoretical research on P8 phosphazene bases 😅

When I did lab safety training for an internship at university they talked about an undergraduate student in another state who had just passed away after catching on fire. She had been using tert-Butyllithium in a syringe when the stopper came out and the chemical go all over her lab coat.

The UCLA story happened when I was in grad school at a different UC. I was in a non-chem lab (printing and presswork), and the new regulations even affected us. We couldn't use our usual cleaning agents on the presses anymore out of safety concerns. No, I'm not a chemist, but this is neat stuff to learn, and I love how these models look, especially in 3D.

I make a pretty mean pretzel. The sodium hydroxide also is what gives pretzels that pretzely flavor. Additionally, it's not just Browning and flavor it's what gives the crust that really smooth shiny exterior. There are alternate recipes that call for baking soda and boiling water instead of sodium hydroxide in water and they provide the color and texture, but not the flavor

he can't keep getting away with that intro joke (please do artificial sweeteners)

19:39 In case you’re wondering, the lower title says „How strong and how hindered can Phosphazene bases be?“ Seeing the results of their work, we can confidently answer their question with „yes.“

Thanks. this list got me some ideas for a synthesis we left on the back burner. I have 2 or 3 ideas I might test after Im done with the current synthesis.

I am fascinated by this channel despite the fact I only have my engineering degree because of rounding in my chem classes.

what happens if you mix a super acid with a super base? extremely violent reaction?

H2 has a pKa of 35 hit me like a truck.💀

That german Reinheitsgebot is about making beer only from three ingredients. That's because people used to use sketchy plants and whatnot to make beer somewhat better or cheaper or both, and also to enhance the buzz. Only problem were poisonous ingredients. So that lead to that law. And now I'm thinking about original Bretzeln. They're like buns in case you don't know. My fantasy right now is: "Let's make buns. Oh, this coal is so expensive. You know what? I read about that chemical that makes baking easier. Let's try. Oh well, our basic bread is faster! But it's also delicate to make. We need to fix the recipe. (a while later) OK this are our buns. Extremely enlarged surface area because people like the taste of that dye. But who cares. It's bread! And it's fast and cheap for us. That's all that matters. Wanna buns? Here! It's a thin structure and salted for taste, but don't think about it. Just enjoy the taste and the price! Come back tomorrow."

🎵All your base (your base) Base, base All your base Are belong to us🎵

Now that i've seen this video, the Basis of this topic is very clear to me

Congratulations on 200k, you make great content! Keep it up brother

Great episode, some of my favorite things are basic, especially bitter organic alkaloids sold in little bags. Like sodium hydroxide, in laundry pods, why, what did you think I meant?

What are Super Bases? ✅ill ✅real ❓might gotta deal ✅pop bottles ✅got the right kinda build ✅cold ✅dope ❓might sell coke ✅always in the air ❌never fly coach

15:16 I think you got the full name for MTBD a little bit wrong The 1 position isn't hydrated, so it would rather be 3,4,6,7,8-Pentahydro [...] And I've been trying to figure out for weeks if not months why the hell on the non methylated analogue to this the two position, a random carbon, is "highlighted" as 2H and not just "included" in the Hexahydro (or if included heptahydro) part Why isn't the 1 position, which is a nitrogen, highlighted as 1H. Or why isn't it just called heptahydro [...] I've asked *3* organic chemistry professors and no-one could give me a real answer AAAHHHH, THIS IS DRIVING ME INSANE

Nice video! Watched 'til the end. One question: how do you choose such candidates for your tier list videos?

At my last job (industrial r&d) I did a bunch of work with free-base guanidine, isolated from the carbonate and dissolved in ethanol. Not a superbase afaik, although I don't actually know its pka in acetonitrile. (also apologies if the "free base" terminology isn't the term actual chemists would use these days, my primary source for this stuff was written in the 50s)

Surprised you didn't include the grignard reagent. It's absolutely a superbase.

Correction at 6:50 -- those protons are thermodynamically, but not kinetically, acidic, likely due to steric hindrance from the acetonide inhibiting deprotonation, and both LDA and HMDS are canonical bulky bases used for formation of kinetic enolates. Also, funny that you put a base in a higher tier because it can form ethers, because I do that with K-carb all the time lol

The extent of my chemistry knowledge is very basic (just O chem for my nursing degree), but I always find your videos very enjoyable and informative, even though I have a hard time understanding what youre talking about. :)

What about ortho-diethynylbenzene dianion, isn’t that like the strongest base synthesised based on it’s proton affinity?

18:00 0.5 more pKBH is more like 3 times stronger, due to logs and all that

Woohoo! Loving the new graphics-no more hitting pause and walking up to examine the TV. Verkade base looks super-cursed. Those NCCNP chains look like they want to snap right off and lay some serious hurt on whatever's nearby. A pKa difference of 0.5 is a ratio of 10^0.5, which is about 3.16, not 5.

Great and very useful video for an inorganic chemist like me. You forgot to mention LiKOR (pronounced liquor) base! It increases the basicity of tBuLi even more by adding KOtBu, nobody knows how it happens though. Nasty stuff

That Chemist = Got That Superbase Boom, Base, Boom, Base-Boom, Base, Boom, Base…

I am glad you didn't said the full name of the bases like the 1,3,4,6,7,8-Hexahydro-1-methyl-2H-pyrimido[1,2-α]-pyrimidine because that would have made the video longer

I didn't know the pretzel thing, thanks for a great bit of random knowledge to have.

Hey! I was wondering if this video would come out soon!! 😮

The potassium hydride lit on fire! Then the hexane lit on fire! Then the lab lit on fire! ...Next, the world.

in a highschool chemistry class one guy thought sodium hypochlorite was calcium carbonate and thought it would be funny to dump down another guys back. as you might expect the bleach disolved into the sweat of his back causing serious burns, would have been a lot worse if i hadnt told both of them there was no calcium carbonate in todays lesson and we were dealing with pure bleach luckily the guy got away with surface level burns and the other guy didnt get expelled.

Don't forget the recent paper about making tBuLi safe to work with. In the right sort of hydrocarbon gel, they were able to leave it uncovered in their lab for months before dropping it in some water, drying it off with paper towels, and then cutting off a slice to use in a reaction.

I want to see a video about antioxidants. What's a chemist's perspective on the hype?

Sheharbano "Sheri" Sangji suffered severe burns from a fire that occurred on December 29, 2008 when a plastic syringe she was using to transfer the pyrophoric reagent tert-butyllithium from one sealed container to another came apart, spilling the chemical, and igniting a fire. Sangji *was not wearing a protective lab coat* and her clothing caught fire, resulting in severe burns that led to her death 18 days later

This is so cool!!!

Great video

P2Et is one of the more readily commercially available phosphazene bases and is really useful for Buchwald-Hartwig reactions.

yes i was in a bitter mood when i clicked on this

only used hidride once, to reduce sugars in a biochemistry lab, it was NaBH4, and the chemistt put the fear of death in me everytime

I have no knowledge of what’s going on in these videos, I feel like Ralph in the Simpsons on the school bus smiling ”Ha-Ha I’m in danger”

Now I understand, the person who called me a "basic bitch" was correctly identifying the bitterness in my soul.

I like NaH, it just works, easy to work with, as long as you planned (as any experiment should be)

You will NOT believe how fast I clicked on this video once I saw it just now! Always so excited when a new That Chemist video comes out!

I think there is a mistake in at 3:10 where after the last equal sign, a"-log10" is missing, which can be seen, when you replace the Ka on the left with the definition of Ka on the very left.

> be chem student > start metal fire > use up all the (incompatible) extinguishers in your lab > take several from the lab next door and use them up too > fire still burning > leave > lab burns down > refuse to elaborate Why would undergrads do this?

*blinks* Is there any example of Cesium Hydride? I mean, the lower you go in that column on the periodic table, the more reactive it gets...

another hood classic joey love to see it 💯 would love to see a pharmaceutical focused chem vid at some point

boy you,super bases, get my heart beat running away

Them 3D models got me excited ❤

I love how you provide all this detailed info and then half the time the ranking is "Because alphabet lol" 😂

Hey and what about the superbases in the sense of polar organometallic chemists like Schlosser's base (nBuLi/tBuOK) or nBuLi/LiDMAE ? They are also superbases but from another point of view : the two bases mixed together get different properties than their individual components.

OK, I get that t-BuLi is S-tier, but why no mention of its evil twin, n-BuLi?

What about Caesium hydride and Rubidium hydride? Those sound like quite exciting superbases!

"All your Base are belong to us."

20:48 Question: Why can't chemists agree to call the Vinamidene with an "een" sound like in spleen and Vinamidine with an "ine" sound like in line? That would probably be a little more helpful, wouldn't it?

I listen to these as i wind down into bed, i absolutely heard Verkade Base as Ricotta Base.

So what makes the phosphazene bases so strong? Do we know? From doing a bit of research I can see that the electron pair participating in the reaction is the one on the N double bonded to the P, but is there any sort of resonance that occurs to stabilize the structure? I figured that that could lead to the double bond resonating among all of the amines connected to the phosphorus as well as putting some of the positive charge on the phosphorus, but I wasn't able to find any sort of literature backing up my hypothesis (at least, not that put it into terms I could translate).

The thumbnail goes incredibly hard

my favorite part was when the base said its base time and based all over the place

I hope chemists don't stop until they make an Ice-nine style superbase or superacid that can just destroy the planet.

Does pKa basically mean just the strength of an acid? So the higher the pKa number, the stronger the acid and so forth? And if the pKa number is small, then that compound is a weak acid, but a strong base? I’m in organic chemistry I right now and I don’t really understand this part :,D

Proton Sponge can definitely live in F-tier. A total faff to use in practice. Name is still cool though

Nice that you did a superbase tier list, I've requested it in the last super acid tier list. Also it also nice to see one of my favorite, derivatives of naphthalene in this video...

I’m watching this like “I like your funny words magic man”

So with such amazing organic chemists out there, can somebody explain to me why we have still not solved the hunger and diet issue in the world? Could we not turn cellulose into sugar, making grass, bamboo and trees a direct source of nutrients? How about extracting tannine from inedible nuts? Or neutralizing whatever toxic is in a flower, making us eat flowers for days.. There are a lot of quickly growing plants out there, what stops us from making them eadible and solving food?

I, a person who doesn't still understand what a super base is, bought TMG in the past for holographic film making. I think it is relevant

We should mix a super fluid super acid with a super cooled super base…. For the memes…

Based video, keep it up

LAB MANAGER, HE'S DOING THE THING AGAIN. WITH THE JOKES.

So you mean to tell me it really is all about that bass?

I don't know shit about chemistry. I'm just here because it's nice to listen to someone knowledgeable and passionate talk about a subject. I was rooting for poor proton sponge to move up the ranks though.

Sponso by ground news? Dude is becoming big!

Not me setting up a reaction with NaH/DMF just the other day... hearing 8:20 made me stop what I was doing 😅

My ansers have been heard. Gotta live tge terrifying super bases.

Ah yes, Laugengebäck, everyones favourite.

Where exactly does the hydrogen ion add to the phosphazene bases? I’d expect it to add to the imine but for all I know it could make a quaternary ammonium. And why are phosphazenes such strong bases? Phosphorus isn’t the most common element in organic chemistry, especially bonded to nitrogen, so it’s hard to guess what’s going on with the poor electrons on that molecule that’d make it so basic.

how about schlossers base and ortho-diethynylbenzene dianion?

My great grandad was a fire Chief and metal fires are scary

In the 3D Models, the angles are fked in some cases, they look like a programm just tried to get 3D from flat Lewis structures. :D not accurate at all. Since there is no crazy stuff, just put them into Avogadro or some other software and use the force field optimisation, to get at least justified angles...

Hey, so your chemical knowledge seems pretty based! sorry I have some questions about electron orbitals in chemistry. So, the lower Mw elements behave intuitively to me, with their S and P orbitals, And the various SP hybridisations. Nice and simple, octet rule conserved. Pi-bonds with SP2 makes sense too. But then you get to the D orbital and beyond and everything is just confusing AF. e.g. 1. Why is a noble gas like Xenon chill with binding to 6 fluor atoms all of a sudden? Isn't it inert or something? Is it because it's the most electronegative atom and it sees "inert" merely as a suggestion? 2. What's the deal with phospherous? Being chill with 3 bonds, but then also with 5? 3. Sulfur is similarly inconsistent. What gives? 4. I don't even pretend to know the weird behavior as you go to heavier elements, so I struggle to formulate a question. Might be a fun topic tho? I feel like that with D orbitals and beyond, quantum mechanics really does its thing, making everything weird and confusing. This is years ago now, but I remember a course on atomic bonds/reactivity. Basically a mix between QM and Chem. I think it has to do with the quantised energy levels and gaps of the different orbitals, like P and D for example, so the lowest new energy level jumps from P to D as you fill the electron shells? Does that sound right? Anyway, I can't be the only one confused by all this, so might be a fun topic for a future video to dive into orbital mechanics (maybe avoiding the mathy Schrödinger Eq stuff) and look at the heavier elements, what happens when the D,F,G orbitals start getting filled, how that shapes in 3D, electron density of those elements for the different types of bonds.

Them bases look mighty tasty

Fighting the urge to taste every base to find the tastiest!

Wonder what your opinion would be on the concept of Francium Hydroxide...

"and it caught on fire. And then hexanes caught on fire" Hahaha I cant 🤣🤣🤣

Even tho im not a chemist and i never will be one this is interasing to watch👍

This video seems to be highly representative of certain types of superbases over others. I see several amidines and guanidines and loads of phosphazenes but not a single nitrogen anion, no alkoxides, one hydride, and one organometallic base.

I have what probably amounts to a silly question for someone watching this video... But anyway I have not been in a chemistry class since 2000 (college 2nd year first year of organic chemistry) near the beginning of the video when talking about the main groups of bases there are some N and P and R ... N is Nitrogen but what are the R represent? And is P phosphorus (please don't tell me that I forgot my symbols) is the R part that will kick the Hydrogen from another molecule and either take it's place bonding to that molecule or does it separate and take the now free hydrogen?

0:50 basically any "Laugengebäck"

i need to improve my normal base so it will be a super base

This video was super based.

Ah finally. that chemist: *purs superbase on me* me: AAAAHHHH STOP IM DYING!!!!! *dies*