What are Super Bases? (Super Base Lore)
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- เผยแพร่เมื่อ 29 มิ.ย. 2024
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Super bases are extremely strong bases, so strong that they get their own special designation. You must be super based if you are watching this video.
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Writer/Producer/Thumbnail Artist - That Chemist (Joey)
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Vinamidine paper - onlinelibrary.wiley.com/doi/a...
PKBH table - doi.org/10.2478/s11532-010-00...
Physico-Chemical Properties of Organosuperbases -doi.org/10.1002/9780470740859...
Pandora's Phosphazene - onlinelibrary.wiley.com/doi/1...
DMF/DMSO/DMA + NaH hazards - pubs.acs.org/doi/10.1021/acs....
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The fact that there has to be services to help determine media bias is telling of how much the media has failed.
What if you mix the most based superbase with the most cringe Superacid?
Kaboom
th-cam.com/video/EhZWQ5_dcNY/w-d-xo.html
You get something super neutral.
HeH + t-Bu-Li
A very exothermic reaction and a neutral product (if stoichiometry fits)
“Yo bro, do you want a superbase?”
“NaH, bro.”
KtBu in DMSO
“He got that Super Base. Boom, Base, Boom, Base-Boom, Base, Boom,Base…”
BrO- even
Hahaha! We used to make "NaH BrOH" jokes back in chemistry class
An increase in pK_BH of 0.5 means that a base is10^0.5 = 3.16 times stronger, not 5 times.
Good catch
We need to redo the whole scale in dB, 7 -> 0dB.
Logaritmic
The Pandora's Phosphazene deserves the mythical SS tier.
Definetly nazi tier stuff
I don't think you want to be in the SS, dude.
*SS* ADISTIC
Looks like there's still some old comrades after all these years. . .
This video is based.
Based on many bases
Basically the most based
basically yeah
That was the most *basic* joke you could make...🤦♂️
Super based.
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.
I wonder sometimes what other hellish things they tried eating before they found something that worked.
I've seen ammonium carbonate listed in the ingredients of some imported cookies. I believe the product has to be thoroughly baked to drive out the resulting ammonia gas, else the product is simply gross. I've never heard ammonium carbonate recommended for home baking, for it would emit a foul odor during baking.
@@SeekingTheLoveThatGodMeans7648 My grandmother uses it at home, and yes it is awful.
My mother made traditional gingerbread a handful of times and used salt of hartshorn (the literal translation of the german colloquial term for it, btw). The stuff smelled awful and the gingerbread took weeks to proove. It came out excellent though.
Sometimes pottash is also used.
I guess those recepies are from a time where soda wasn't available.
We have the ammonium one in Sweden, it's used in a cookie called Drömmar (Dreams), the cookies are really good but it's hell opening the oven if baking them at home 😂
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.
Lol
@@Sniperboy5551You’re laughing out loud because someone died?
I feel like everyone taking undergrad chem hears that story.
I heard that too! Our professor even shared the article, and also emphasised that's why our labcoat design is the tear-from-the-front type instead of the button-up type, because that few seconds you take to unbutton instead of tearing the labcoat off can cost your life.
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 😅
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
I guess you could say sodium hydroxide makes a basic pretzel.
@@MalleusSemperVictor that was magnificent. I'm using that
Yeah, its not as good. Thats how I've made homemade pretzels. Its almost a pretzel but somethings missing. Samething happends when I make homemade doughnuts.
I dont know how I feel about pretzel dough being washed in a sodium hydroxide solution.
@@kathleenrobertpogue6818it’s a pretty dilute solution though…
@@kathleenrobertpogue6818 yeah you're only using like a quarter cup of sodium hydroxide in a quart or two of water.
I've got it on my hands tons of times and if I don't wash it off quickly at worst my hands get a little tingly.
It's really no big deal
As for the doughnuts..... Was it the glaze or the donut itself? If you can tell me your recipe I might be able to give you a pointer or two
he can't keep getting away with that intro joke
(please do artificial sweeteners)
We have one planned - the team working on it is still working on it :)
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.
Awesome! I hope it works out :)
The proff found the Idea good but we are kind of struggling with the last step of a long synthesis so its going to be later. We get the desired product but only a tiny yield.@@That_Chemist
I am fascinated by this channel despite the fact I only have my engineering degree because of rounding in my chem classes.
Congratulations on 200k, you make great content! Keep it up brother
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."
huh
what happens if you mix a super acid with a super base? extremely violent reaction?
probably one of the most violent reactions - Chemical Force should try it out ;)
strongest base vs strongest acid, that'd be cool to see
@@That_Chemist He did fluoroantimonic acid vs. t-buli, it wasn't that violent tho. Just kinda fizzled out very quickly
@@That_Chemist Well yeah, something super duper exothermic, but assuming there's anything left of the lab equipment, would there be something special about the resulting compound, like being some super stable molecule, bound crazy tight together?
@@SeekingTheLoveThatGodMeans7648 no
Now that i've seen this video, the Basis of this topic is very clear to me
H2 has a pKa of 35 hit me like a truck.💀
🎵All your base (your base)
Base, base
All your base
Are belong to us🎵
Hihihii😊
Nice video! Watched 'til the end. One question: how do you choose such candidates for your tier list videos?
Surprised you didn't include the grignard reagent. It's absolutely a superbase.
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?
Quiting is easier than you'd think you can if you want to God bless.
@@longhairdontcare122 Thank you for that, few people would have bothered. I retired from amateur pharmacy seven years ago and currently support the Columbian economy with the absurdly expensive coffees I enjoy.
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. :)
I didn't know the pretzel thing, thanks for a great bit of random knowledge to have.
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
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
Hey! I was wondering if this video would come out soon!! 😮
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
I'm not entirely sure that this sentence contains english 🤔😅
@@ivolol you're writing that reply to a chemist commenting on a video about chemistry? interesting choice
@@jacoboleary9076i think it was meant as a compliment
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
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 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
yes i was in a bitter mood when i clicked on this
18:00 0.5 more pKBH is more like 3 times stronger, due to logs and all that
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)
Free base is still kosher
Great video
This is so cool!!!
another hood classic joey love to see it 💯 would love to see a pharmaceutical focused chem vid at some point
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
P2Et is one of the more readily commercially available phosphazene bases and is really useful for Buchwald-Hartwig reactions.
I want to see a video about antioxidants. What's a chemist's perspective on the hype?
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
That Chemist = Got That Superbase
Boom, Base, Boom, Base-Boom, Base, Boom, Base…
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.
It was nBuLi
@@That_Chemist Oh, sure enough. It looks like they also got secBuLi to work somewhat, but not well enough to expect tBuLi to work.
What about ortho-diethynylbenzene dianion, isn’t that like the strongest base synthesised based on it’s proton affinity?
Yeah why wasn't it mentioned?
in the gas phase yes but afaik there are no stable salts of it that are bench stable.
@@penteractgaming which makes sense then if that chemist is genuinely referring more to actual compounds that he's come across and used. Similar to theoretical calculations of the explosive properties of octanitrocubane vs the number of people who have genuinely encountered it in their work.
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...
The potassium hydride lit on fire! Then the hexane lit on fire! Then the lab lit on fire!
...Next, the world.
I like NaH, it just works, easy to work with, as long as you planned (as any experiment should be)
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.
How does one make a gaffe of that magnitude. I hope he doesn't expect to be a chemistry major.
He should have got expelled.
Them 3D models got me excited ❤
> 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?
What about Caesium hydride and Rubidium hydride? Those sound like quite exciting superbases!
boy you,super bases, get my heart beat running away
The thumbnail goes incredibly hard
I love how you provide all this detailed info and then half the time the ranking is "Because alphabet lol" 😂
I hope chemists don't stop until they make an Ice-nine style superbase or superacid that can just destroy the planet.
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 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.
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”
Sponso by ground news? Dude is becoming big!
I listen to these as i wind down into bed, i absolutely heard Verkade Base as Ricotta Base.
my favorite part was when the base said its base time and based all over the place
Proton Sponge can definitely live in F-tier. A total faff to use in practice. Name is still cool though
OK, I get that t-BuLi is S-tier, but why no mention of its evil twin, n-BuLi?
Based video, keep it up
"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?
Them bases look mighty tasty
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
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.
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).
*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...
I was so happy seeing beloved DBU in S-Tier. You Sir, warmed my heart and I'm not afraid to admit it!
Now I understand, the person who called me a "basic bitch" was correctly identifying the bitterness in my soul.
So you mean to tell me it really is all about that bass?
I’m watching this like “I like your funny words magic man”
Not me setting up a reaction with NaH/DMF just the other day... hearing 8:20 made me stop what I was doing 😅
pubs.acs.org/doi/10.1021/acs.oprd.9b00276
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.
My ansers have been heard. Gotta live tge terrifying super bases.
I like your funny words magic man
We should mix a super fluid super acid with a super cooled super base…. For the memes…
What's so bad about that? (I'm a high schooler in ap chem, I know, very little chemistry)
Even tho im not a chemist and i never will be one this is interasing to watch👍
Slight mistake : On a logarithmic scale, a difference of 0.5 is just a little bit above 3 times, not 5.
5 times is a difference of 0.699.
Youre taught to not mess with acids because they are dangerous, but atleast the dont just explode or some other variety of potentially destroy everything without corroding any of it
David Leigh reported rotaxane superbase recently
"and it caught on fire. And then hexanes caught on fire"
Hahaha I cant 🤣🤣🤣
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.
All about that base
Wonder what your opinion would be on the concept of Francium Hydroxide...
My great grandad was a fire Chief and metal fires are scary
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?
R stands for Radical and it just means “some carbon containing thing” - it’s to generalize things
LAB MANAGER, HE'S DOING THE THING AGAIN. WITH THE JOKES.
0:50 basically any "Laugengebäck"
Fighting the urge to taste every base to find the tastiest!
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
great video shame the dea don’t think like that for certain chemicals made for research just ban them just in case of abuse crazy but might be bloody useful for something one day ❤
how about schlossers base and ortho-diethynylbenzene dianion?