Idea for you: mechanisms tier list. Undergrad O Chem covers about a million of them and it would be interesting to see what is actually useful and what is just taught to make sure it gets covered. Edit: He made it and the link is in one of the replies (can't get my phone to copy it).
I learnt so many mechanisms and now remember none of them (since i don't do ochem daily) eventually you remember the basic stuff like nucleophiles, acidity etc
What's also interesting to me is that I've started to realized that every University will teach you basic reactions that everyone should know like Diels-Alder, Friedel-Crafts etc. but they may differ in some more advanced stuff and I'd like to see the difference
I don't know if there would be much to say, but a cursed notation tier list. For example, one of my friends used to draw benzene rings with the double bond OUT of the ring. Still gives me trauma nowadays.
I would love a "cursed inorganics" video. In the vein of "things I will not work with". :P FOOF and ClF3 come to mind, along with "how many nitrogens can we bond to each other" explosives.
@@tttITA10 Even worse is what A. G. Streng of Temple University did while testing its reactivity. Amongst other things, he reacted it with: * Ethanol * Ammonia * Red phosphorus * Elemental chlorine (*twice!*) * Perchloryl fluoride * Water ice * And last, but not least... *Chlorine trifluoride* The guy was the textbook definition of "mad scientist".
Speaking from experience, inorganic chemistry and heterogeneous catalysis reactions in particular are the most cursed type of chemistry to exist: some of the intermediate species on metal particles aren't just cursed, they're an insult to all of God's creation.
as someone who isn’t too into chemistry, this is by far one of the most interesting videos i’ve seen in a while. i had no idea what any of these are, but your explanations of each molecule made me understand what each of these do. crazy good video man, keep it up.
I’m so glad to hear that :) TH-cam started showing my videos to a wider audience, and i really hope that it is educational for non-experts. Even if it sparks your curiosity, I would be glad to be a part of it!
That compound is an S++ immediately. Gold(II) not dimerizing (as in gold(II) sulfate), and having four xenon(0) ligands. Truly a curse from the underworld.
Was that laughingly stated "although other members of the chemistry community have struggled to synthesise them in a timely manner but perhaps there's a good reason for that." at 16:32 a reference to Ex&F? xD
@@evanlabrant5448 I know, and he's doing pretty well for someone doing as he himself put it 'shitty jam jar chemistry in my backyard shed'. I'd say the only memeworthy fuckup he made was with powering the UV-LEDs.
@@thor1829 Don't get me wrong, Tom's channel is memeable chem fuckup pay dirt. That's why (IMHO) it's the most entertaining DIY chem channel on YT. The fact that some of the stuff he does works at all is mind boggling, then add on the comedy and it's pure gold. I'm a big Tom fan, just in case it isn't obvious lol.
If bond strain is a requisite for being cursed, epoxides and beta-lactones should have a spot on this list. Not to mention that the simplest members (ethylene oxide and b-propiolactone) are astonishingly potent carcinogens and can undergo explosive polymerization.
According to the famous rocket chemistry book "Ignition!" by John Drury Clark, ethylene oxide can also be used as a monopropellant rocket fuel, albeit not a particularly powerful one. Allegedly, if ignited with a glow plug, it "burns" itself by converting to a mixture of carbon monoxide and methane. While no commercial rocket was ever developed to use this, it was apparently used in a few APU type gas generators.
My knowledge of chemistry is basically a high schooler’s and I only recognized a few chemical names/types, but I was still amused by the wild and wacky chemical structures. I’m going to watch your mycotoxin video next.
I know it's an organic coordination compound rather than just a purely organic compound, but I'm sad that Chromium(II) acetate hydrate didn't make the list with its *quadruple bond.*
The anhydrous molybdenum analog is a beautiful yellow, I've also made the Mo2(2,6-C6H3(OMe)2)4 analog which is a deep purple by transmission and hot pink by reflection.
What’s amazing is that several of these are represented in the scaffolds of natural products. The precise biosynthetic pathway of enediynes remains one of the unsolved holy grails of our field. Natural product enediynes (i.e. Calicheamicin) are definitely S tier to me haha.
Wow, I looked up calicheamicin on wikipedia and it really should NOT exist. That enediyne is in an unholy bicyclic ring thing, and elsewhere there are 3 sulphur atoms in a chain! Of course, the sugar units could not be normal. They had to be aminated. And linked with an S bridge. And an N-O bridge! And an Iodine atom. Just because.
Not even kidding, saw this in my feed and thought "I wonder if decaborane is on that list". Sure enough! It's a wonderful oddball, supposedly smells of sulfur even though it has no thiol groups, but I have no plans to verify this.
Nowadays catanes are often relatively selectively formed by using metal coordination between an open ring and a closed one, and then closing the second ring. Sometimes a covalent bond bond is used that is broken afterwards, hydrolysed for example. In the past it was pure luck, so they'd repeat the same step over and over and would get a less than 1% yield over 20 repetitions.
My whole undergrad research was about allenes! They're a massive pain in the ass to make, but they're stable once you make them. We were eventually trying to make Allenes with naphthalene rings on both ends with one end being e- donating and one being e- accepting then looking at the crystal properties of the molecules.
I don't have much more than a high school chem class to my name, but all I know is that the more Ns you can see in the diagram, the faster you should run away.
In Chemistry class we had to build structures for C6H6. What funny is that we actually came up with molecules like Dewar Benzene and Prismane, the latter our teacher didn't even know about.
Yeah for sure I've heard some of those words before the Fr though I've seen shapes today I never thought I'd never thought possible and thank you for enlightening my day like that, TC!
As a data analyst/software engineer I have no idea what any of this means but some of the glimmers of concepts I'm getting here actually scare me, so good job picking out the cursed molecules
I had to rewatch the first half of this video because I was entirely convinced that none of these existed- I thought you were just pulling my leg, especially with squaric acid 😭. When you got to Metformin (I knew what that was already), I started looking some of these molecules up and had to take some time to process that these are actually real… “Ladderanes” oh my god
I had an idea for a series where you could go through each decade and discuss the 5ish most important discoveries/accomplishments in chemistry and talk about them like your “important papers” series. Just a thought, great video!
Catenanes are synthesized by forming copper-nitrogen coordination compounds with two half rings and then doing a cyclization reaction to close the rings, then copper is hydrolized and catenane is formed. Nobel prize 2015, quite interesting stuff by JP Sauvage.
Thats one way for sure. Our group just published a JACS on using these types of catenanes in gels as a tunable crosslinker. You can basically use any kind of templation strategy though. Other common ones are H bonding and donor acceptor
Just wanted to say thanks for these. I've learned a lot of new chemistry had never heard of Azete or Thiete. These exotic compounds are my true passion. That bullverine is wicked it must be a potent carcinogen. I think about aromaticity when that compound is described with the resonant bonds neither here nor there. Love this show!
This is the first time I saw the chemical structure of Metformin and Chlorhexidine, and I have to tell you, I'm gonna be a lot more skeptical of these molecule in the future. Because both look like ingredients for weapons of mass destruction...
PLEASE DO A CURSED INORG TIER LIST I have spent so much time observing the most cursed shit coming out of the next door lab, like it’s become my favorite pastime and I’d love to see this codified.
These are an automatic S tier from me: [1.1.1]propellane (Surprisingly stable super-strained cycle, with ring strain of over 100 kcal/mol, or 418,4 kJ/mol.), bicyclo[1.1.1]pentane (A highly strained ring, it's useful for bioactive molecules.), catenanes (mechanical bonds), cubanes (cube), 1-methylcyclopropene (used to preserve apples), 2-cyclopropenecarboxylic acid (toxic but is removed by polymerization), prismane and its derivatives (explosive hydrocarbon), Dewar benzene and its derivatives, benzynes, any stable carbon oxides other than carbon monoxide and carbon dioxide (carbon suboxide, mellitic anhydride, ethylenetetracarboxylic dianhydride), pentacyanocyclopentadiene (Superacidity is impressive for a carbon acid with only nitrogens aside from its acidic hydrogen and its carbons. This shows the power of cyano as an electron withdrawing group.), moniliformin and squaric acid (both compounds represent vinylogous analogues of carboxylic acids, the former toxic, the latter, when twice-deprotonated, aromatic), ladderanes, allenes and (especially very long) cumulenes, ketenes (The parent is toxic and is a decomposition product of vitamin E, found in e-cigarette juice, which caused a spike in lung disease in the United States in 2020. The derivatives and their acetals are useful reagents.), azetes (especially of the Figueroa-Valverde type), dithietes, bullvalene, enediynes (chemotheraupetic drugs that are highly mutagenic), [12]helicene, dodecahydroxycyclohexane (stable for a perhydroxyaliphatic - or here, alicyclic - compound), superphane and cyclophanes, o-carborane, decaborane. Automatic A tier: Bodipy (Boron trifluoride, if hydrolyzed to, is toxic, and will hydrolyze to HF. Bodipy series represent useful ligands.), chlorhexidine (disinfectant), fusafungine (antibiotic), metformine (used to balance glucose levels in type 2 diabetics), 3-methyl-2H-furo[2,3-c]pyran-2-one (karrikinolide, the chemical of smoke), (3a¹s,5a¹s)-3a¹,5a¹-dimethyl-3a¹,5a¹-dihydropyrene (look at that name!), calix(4)arene (useful ligand). Other molecules that are an automatic S tier from me: Quadricyclane (photoelectricity), olympiadane (created just because), dioxygen difluoride (automatic), chlorine trifluoride (automatic), NanoKid (educational chemical), NanoCar (four buckminsterfullerene derivatives acting as wheels), buckminsterfullerene (room-temperature stable molecular carbon allotrope), cyclo[18]carbon (the chad explosive, consisting of just carbon), the first cyclocarbon to be synthesized, an all-carbon electron acceptor), polyynes (of astrochemical importance, especially long polyynes). Cursed chemicals are interesting in one way or another. I didn't rate anything below A here.
You noted, but kind of glossed over that mellitic anhydride is a mineral, meaning it's naturally occurring geologically which is pretty neat imo. There are a decent amount of complex, cursed biochemistry, but not much cursed geology.
Oh, the chemists I knew from University (late 90s) were VERY keen on safety while we physicists were looking for the lost 2W laser beam with a piece of black cardboard with the laser running or cleaning laser active polymers off glassware with dichromic acid ..... Looking back, I'm surprised that nothing happened.
@@wernerviehhauser94 my university is particularly proud of only ever having one postgrad student permanently blind themselves with a laser beam. For the most part we're more of a danger to extremely expensive equipment (laser optics) than to ourselves
I usually watch chemical force for cursed inorganics Like out of nowhere he grabs a 30 years old ampoule of some chemical that you won't even think existed
Sulfur nitride, sulfur hexafluoride, hydrogen polysulfides, krypton/xenon oxyfluorides, diimine, orthoperiodic acid, diphosphorus tetraiodide, borazine. Most of those are like C tier tho.
I took a year of organic chemistry in college. I was just a math major who liked making potions. And what did I get out of it? Now I can appreciate this video
Hey ! Love your work in general and the tier list series particularly ! Can be inspiring to see those twisted structures, somehow haha. I can relate for the helicene (M) or (P) enantiomers that they are usually made as racemic mixtures and then separated on a chiral HPLC. I'm working in a group where almost everyone make those.
Different approach here, working in a group making selectively one helicene enantiomer. Racemates are still synthesized for developing chiral LC methods to determine EE, but we can get 98+% of EE with some catalysts, conditions and substituents!
I work with catenanes and rotaxanes, they aren't cursed per se but often pretty Hard to make. Also we make tBu-calixarenes in our introductory o-chem lab, the tBu groups can the be removed by a retro-Friedel Crafts rxn to yield the calixarene shown in your Video, which works quite well
I know they're not that cursed, but buckyballs with noble gases trapped inside them are just the funniest things to me. Also, you should include the helium dimer (He2) in an inorganic sequel video.
I accidentally made an allene once by the reaction of pyrrolidinone with propargylbromide using NaH as a base. The allenyl pyrrolidinone was surprisingly stable. I was also shocked that I could column it without problem.
Enediynes are amongst the most interesting molecules I've read about due to their reactions. There are natural enediynes synthesized by some microorganisms that act as toxins that kill competitors by directly cleaving DNA with biradicals. Whilst I am still skeptical of the claims of their antitumor properties, I definitely think they should be given more attention in microbiology and pharmacology.
I hat to synthesise an Allene as a part of a undergrad lab course, with 3 other students given similar analogues. Even though the synthesis failed for all four it was because of the old, almost completely air oxidised wittig precursor. So instead we hab to hydrolise a Alleen containing ester, which tolerated 4 hours of reflux in 50% Ethanol/Water with NaOH quite well. The alleen for me was 2-benzyl-5,5-dimethylhexa-2,3-dienoic acid hzdrolised from the corresponding ethyl ester. For the synthesis it was intended to react an acid chloride with stable wittig reagent and according to the supervisor it was usually successful with yields around 50%.
Another very nice and informative presentation. I was happy to see ketenes on the list. My graduate work dealt with the cycloaddition reactions of chlorocycanoketene, used to prepare beta-lactams by cycloaddition reaction to imines.
Look up Mobius Orbitals - essentially there's an excited state of a pi-conjugated system with only one node, each p-orbital is twisted slowly around the ring.
In our class, the molecule we consider the most cursed is 3,3-Diethylpentane which has a structure strikingly similar to swastika sign. In india, since we use the one that is at right angles and it's a holy symbol, it's absolutely no problem in our schools or in public places. But since our class loves dark jokes, we decided to tilt it at an angle of 45° to make it absolutely cursed.....
as a non chemistry person i would put methyl cyclopropene in s tier. from what you said it sounds pretty cool but to non chemist eyes it looks like a little beaker and i think its cute
Helicenes can be formed using different approaches. One strategy is to use alkyne hydroarylation reactions to form the rings. When applying transition metal catalysts, if you use appropriate chiral ligands, you can get enantiomeric excess of up to 98+% for the helicenes. Depending on conditions, catalysts/ligands and the substrate, there are also some side products with interesting optical properties. In general, helicenes are interesting, but at the same time pretty annoying. As an analytical chemist supporting the organic people's workflow, the tendency to crystallize within hours from nearly any non-chlorinated solvent and then turn into completely insoluble bedrock drives me insane on a daily basis.
Yesss, my boi pentacyanocyclopentadiene! :D Another cool symmetric ring molecule is Sulflower. Essentially 8 thiophene rings fused side-to-side, forming a flowery ring. Also means the molecule has no hydrogen left. Not sure how cursed you would rate it, but it is definitely an aesthetically pleasing sight!
Not only have I prepared allenes, I have prepared iodo-allenes (via SN2' displacement of the precursor propargyl alcohol with HI/CuI). Somehow, allenyl-X is thermodynamically more stable than propargyl-X. This is not to say allenes are OK. They are not, they are terrible! I was trying to purify a low MW allenyl iodide via distillation (per a lit method) and it exploded the first time I tried. The next time I modified to distill under reduced pressure, and it exploded again. Finally, I distilled 1) under pressure and 2) from dodecane so that it never went dry. At last, no explosion. 0/5 do not recommend allenes.
Squaric acid’s name 💯💯💯 You’re correct that it doesn’t contain a carboxylic acid, but it is a double vinylogue of a carboxylic acid (i.e. a double vinylogous acid) meaning that there is a double bond between the OH and the carbonyl - very cool functionality.
You can write it as (Cp*-C-Me)²⁺. You heard that right, *methyl(η⁵-pentamethylcyclopentadienyl)-λ⁰-methanediium.* Carbon tries to be like metals in both hexamethylbenzene dication and benzene dication ((Cp-C-H)²⁺), η⁵-cyclopentadienyl-λ⁰-methanediium). (Yes, I used "λ⁰-methanediium" for CH₂²⁺ from which I put the Cp/Cp* group on that carbon.)
@@californium-2526 It's amazing what you can get to stick together when you have the electron density of an aromatic ring and total electron desert everywhere else, at least I think that's a reasonable way to think about it??? And yeah, the naming conventions just kinda break down when you come to hypervalent compounds so go wild.
@@samheasmanwhite I had to use the organometallic nomenclature for the benzene dications. There's decamethylsilicocene, so, when's the carbocene analogue (with two η⁵-Cp-derived ligands) gonna come out?
@@californium-2526 Hmm, as far as I am aware; Cp*1+ can't contribute less than four electrons so for actual pyramidal bonding that would have to be bonding with a 4+ carbon atom and the bonding orbitals would be really mashed into each other since carbon is so small, so if it was stable it would have to be a coordination complex rather than actual bonding. I found a paper (doi:10.1021/om980737l) that does a computational study and they think the carbon will end up just bonding to one carbon in each ring to make a carbene, or if using Cp instead of Cp* it would form phenylcyclopentadiene, but who knows, maybe it could work :) What's the lambda notation? I don't know much about this and couldn't find out what it is.
@@samheasmanwhite Lambda notation, used in hypervalent compounds, e.g. organo-hypervalent-halogen compounds, e.g. iodoxybenzoic acid, IBX, phenyl(bis(trifluoroacetoxy)-λ³-iodane; cyclic organophosphorus(V) and organosulfur(IV) or (VI) compounds. IUPAC assumes that elements in these groups will normally have this much bonding available: 4 for group 4a, 3 for groups 3a and 5a, 2 for group 6a, 1 for group 7a and 0 for group 8a. You don't use the lambda notation for that. You go higher or lower than that, and you use the lambda notation (generally, the exceptions involve onium and ate ions that arise from species which had a "normal amount of" bonding, e.g. ammonium, phosphonium, oxonium, sulfonium species; and organoxenon compounds - nobody seems to use "xenane" for such compounds. However, if it arised from a species where the lambda notation was used, you use the lambda notation, e.g. sulfoxonium from a sulfoxide).
![[LIVE] BABYMONSTER(베이비몬스터) - DRIP | 두시탈출 컬투쇼](http://i.ytimg.com/vi/UG05pxLGwzc/mqdefault.jpg)
As a non-chemist, it almost feels like you're pulling my leg with "squaric acid" and "ladderanes" - what's next - low-graderenes, elcheaporenes? ;)
haha
@@That_Chemist Are you?
@@dizzydaisy909 I am not
Everyone's hahaing until the sequel video introduces the legpullerenes
@@Tobbzn The sequel should have buckminsterfullerene, which is 60 carbon atoms arranged like a soccerball.
And no, I'm not pulling your leg.
Idea for you: mechanisms tier list. Undergrad O Chem covers about a million of them and it would be interesting to see what is actually useful and what is just taught to make sure it gets covered.
Edit: He made it and the link is in one of the replies (can't get my phone to copy it).
Great idea. Rank them by personal favorite, accessibility, relative usefulness, and danger/risk issue
I second this!
I learnt so many mechanisms and now remember none of them (since i don't do ochem daily) eventually you remember the basic stuff like nucleophiles, acidity etc
Yes please
What's also interesting to me is that I've started to realized that every University will teach you basic reactions that everyone should know like Diels-Alder, Friedel-Crafts etc. but they may differ in some more advanced stuff and I'd like to see the difference
Literally any molecule "synthesized" by Figueroa group should go to SSS tier.
100%
I don't know a lot about chemistry, can you elaborate on that?
Or F tier
Hiw about Klapötke group?
@@samuelbucher5189 no
I don't know if there would be much to say, but a cursed notation tier list. For example, one of my friends used to draw benzene rings with the double bond OUT of the ring. Still gives me trauma nowadays.
I would love to see this. Take suggestions for notation from people on the discord, maybe?
Anyone who draws their hexagons as like a lozenge shape with right angles on the ends mildly annoys me. What, you can't draw a 120 degree angle?
@@estherstreet4582 Sometimes during Org chem I was so lazy, I just wrote the word Aryl in a circle.
@@thor1829 based
A professor of mine once drew a benzene as a rectangle with 2 implied carbons in the middle of the long sides...
I would love a "cursed inorganics" video. In the vein of "things I will not work with". :P
FOOF and ClF3 come to mind, along with "how many nitrogens can we bond to each other" explosives.
Thioacetone.
FOOF seems scary just as a concept :O
@@tttITA10 Even worse is what A. G. Streng of Temple University did while testing its reactivity.
Amongst other things, he reacted it with:
* Ethanol
* Ammonia
* Red phosphorus
* Elemental chlorine (*twice!*)
* Perchloryl fluoride
* Water ice
* And last, but not least... *Chlorine trifluoride*
The guy was the textbook definition of "mad scientist".
@@tttITA10 Does it react with F-O-O-O-O-O-O-O-O-O-O-O-F though?
@@u.v.s.5583 *Flinch*
This is such niche content for an even more niche audience and I absolutely love it.
Or it’s niche content for a wider audience - I mean at 100k views I don’t thing it’s niche anymore
If you do inorganic cursed structures, don't forget metal-metal quintuple bonds
Speaking from experience, inorganic chemistry and heterogeneous catalysis reactions in particular are the most cursed type of chemistry to exist: some of the intermediate species on metal particles aren't just cursed, they're an insult to all of God's creation.
ooo definitely please do this!! i had heard of ligand stabilized metal-metal quatruple bonds, but not quintuple
Dimolybdenum and ditungsten, which are known in the gaseous phase, contain a metal-metal *sextuple bond.*
as someone who isn’t too into chemistry, this is by far one of the most interesting videos i’ve seen in a while. i had no idea what any of these are, but your explanations of each molecule made me understand what each of these do. crazy good video man, keep it up.
I’m so glad to hear that :)
TH-cam started showing my videos to a wider audience, and i really hope that it is educational for non-experts. Even if it sparks your curiosity, I would be glad to be a part of it!
My PhD project in the late '70's early 80's was trying to synthesise monocyclic azetes. Its cool to see someone else has even heard of them
:)
You gotta do inorganic, that's where the real cursed stuff happens. Tetraxenonogold for example.
I will in due time
xenon... bonding... to gold? that sounds illegal
That compound is an S++ immediately. Gold(II) not dimerizing (as in gold(II) sulfate), and having four xenon(0) ligands. Truly a curse from the underworld.
@@californium-2526 it's so cursed that you can only produce it by using the strongest acid in the world
Was that laughingly stated "although other members of the chemistry community have struggled to synthesise them in a timely manner but perhaps there's a good reason for that." at 16:32 a reference to Ex&F? xD
Yes he's trying to make cubane for 3 years already and is failing
To be fair, Tom is doing it in his backyard shed with mostly off-the-shelf supplies and basically no analytical instrumentation.
@@dexter2392 I would hardly say he is failing (except and understanding the relationship between voltage and current).
@@evanlabrant5448 I know, and he's doing pretty well for someone doing as he himself put it 'shitty jam jar chemistry in my backyard shed'. I'd say the only memeworthy fuckup he made was with powering the UV-LEDs.
@@thor1829 Don't get me wrong, Tom's channel is memeable chem fuckup pay dirt. That's why (IMHO) it's the most entertaining DIY chem channel on YT. The fact that some of the stuff he does works at all is mind boggling, then add on the comedy and it's pure gold. I'm a big Tom fan, just in case it isn't obvious lol.
If bond strain is a requisite for being cursed, epoxides and beta-lactones should have a spot on this list. Not to mention that the simplest members (ethylene oxide and b-propiolactone) are astonishingly potent carcinogens and can undergo explosive polymerization.
Those do sound interesting, and definitely cursed
According to the famous rocket chemistry book "Ignition!" by John Drury Clark, ethylene oxide can also be used as a monopropellant rocket fuel, albeit not a particularly powerful one. Allegedly, if ignited with a glow plug, it "burns" itself by converting to a mixture of carbon monoxide and methane. While no commercial rocket was ever developed to use this, it was apparently used in a few APU type gas generators.
My knowledge of chemistry is basically a high schooler’s and I only recognized a few chemical names/types, but I was still amused by the wild and wacky chemical structures. I’m going to watch your mycotoxin video next.
great :)
I know it's an organic coordination compound rather than just a purely organic compound, but I'm sad that Chromium(II) acetate hydrate didn't make the list with its *quadruple bond.*
The anhydrous molybdenum analog is a beautiful yellow, I've also made the Mo2(2,6-C6H3(OMe)2)4 analog which is a deep purple by transmission and hot pink by reflection.
Interesting
Now I wonder if dicarbon molecules are somewhat stable as a low-pressure gas...
Yeah, that quadruple bond is definitely cursed
What’s amazing is that several of these are represented in the scaffolds of natural products. The precise biosynthetic pathway of enediynes remains one of the unsolved holy grails of our field. Natural product enediynes (i.e. Calicheamicin) are definitely S tier to me haha.
Wow, I looked up calicheamicin on wikipedia and it really should NOT exist. That enediyne is in an unholy bicyclic ring thing, and elsewhere there are 3 sulphur atoms in a chain!
Of course, the sugar units could not be normal. They had to be aminated. And linked with an S bridge. And an N-O bridge!
And an Iodine atom. Just because.
Not even kidding, saw this in my feed and thought "I wonder if decaborane is on that list". Sure enough! It's a wonderful oddball, supposedly smells of sulfur even though it has no thiol groups, but I have no plans to verify this.
Never thought I'd be watching a 20 minute video on organic chemistry unless it was a week before an exam, but here I am.
I hope you enjoyed it :)
Enjoy the topic but hated the class.
>You synthesize Carborane.
>It's a 1.
>It explodes somehow and you take 10 fire damage.
a chemistry-themed DnD game is a great idea for content (I won't do this, but someone should!)
Nowadays catanes are often relatively selectively formed by using metal coordination between an open ring and a closed one, and then closing the second ring. Sometimes a covalent bond bond is used that is broken afterwards, hydrolysed for example.
In the past it was pure luck, so they'd repeat the same step over and over and would get a less than 1% yield over 20 repetitions.
yeah its a cool procedure
My whole undergrad research was about allenes! They're a massive pain in the ass to make, but they're stable once you make them. We were eventually trying to make Allenes with naphthalene rings on both ends with one end being e- donating and one being e- accepting then looking at the crystal properties of the molecules.
interesting!
I don't have much more than a high school chem class to my name, but all I know is that the more Ns you can see in the diagram, the faster you should run away.
true!
In Chemistry class we had to build structures for C6H6. What funny is that we actually came up with molecules like Dewar Benzene and Prismane, the latter our teacher didn't even know about.
You guys were some smart young bucks
16:34
Damn, you really had to call out extractions and ire like that
Hahaha - you got me
Yeah for sure I've heard some of those words before the
Fr though I've seen shapes today I never thought I'd never thought possible and thank you for enlightening my day like that, TC!
Glad you learned something :)
As a data analyst/software engineer I have no idea what any of this means but some of the glimmers of concepts I'm getting here actually scare me, so good job picking out the cursed molecules
If you do a tier list on inorganic molecules, please review DIBORANE. I can't get my head around that one.
*looks it up* WHAT THE F IS THIS
@@Mercure250 3-center-2-electron bondings be like!
@@californium-2526 Yeah lol that was new to me, both a neat find and a cursed find
i'm more of a mathematician
, and i know absolutely nothing about chemistry, but this video was really interesting and entertained to watch, great job
Thanks :) I have another one tomorrow!
me, who understands chemistry on the level of H + 2O = H2O : Ummm... yes.
Ahah ahaha me
It's two H molecules and one O molecule...
@@iPlayOnSpica Yes. I know
Since pentacyanocyclopentadiene is so cursed, I propose we call it the Devil's Paddlewheel
I've been watching Extractions and Ire's cubane series for over a year, I'd say that's fairly cursed
As soon as he mentioned the struggle for a timely synthesis I knew this was a cheeky hint at E&Ire ;))
I had to rewatch the first half of this video because I was entirely convinced that none of these existed- I thought you were just pulling my leg, especially with squaric acid 😭. When you got to Metformin (I knew what that was already), I started looking some of these molecules up and had to take some time to process that these are actually real…
“Ladderanes” oh my god
I had an idea for a series where you could go through each decade and discuss the 5ish most important discoveries/accomplishments in chemistry and talk about them like your “important papers” series. Just a thought, great video!
Interesting!
Catenanes are synthesized by forming copper-nitrogen coordination compounds with two half rings and then doing a cyclization reaction to close the rings, then copper is hydrolized and catenane is formed. Nobel prize 2015, quite interesting stuff by JP Sauvage.
Very cool!
Thats one way for sure. Our group just published a JACS on using these types of catenanes in gels as a tunable crosslinker. You can basically use any kind of templation strategy though. Other common ones are H bonding and donor acceptor
Gracias joseluis, casi tengo que explicarselo yo
I had a professor use several of these on assignments and exams to teach point groups in an undergrad course, it was so hard
Yeah - it do be like dat
Not neccessarely cursed, but funny looking, all the molecules from Old MacDonald Named a Compound: Branched Enynenynols
I love this comment
@@That_Chemist What makes it even better is that this is a legit paper in published in ACS
Just wanted to say thanks for these. I've learned a lot of new chemistry had never heard of Azete or Thiete. These exotic compounds are my true passion. That bullverine is wicked it must be a potent carcinogen. I think about aromaticity when that compound is described with the resonant bonds neither here nor there. Love this show!
Thanks!
This is the first time I saw the chemical structure of Metformin and Chlorhexidine, and I have to tell you, I'm gonna be a lot more skeptical of these molecule in the future. Because both look like ingredients for weapons of mass destruction...
Yeah
PLEASE DO A CURSED INORG TIER LIST
I have spent so much time observing the most cursed shit coming out of the next door lab, like it’s become my favorite pastime and I’d love to see this codified.
It will happen - stay tuned!
These are an automatic S tier from me: [1.1.1]propellane (Surprisingly stable super-strained cycle, with ring strain of over 100 kcal/mol, or 418,4 kJ/mol.), bicyclo[1.1.1]pentane (A highly strained ring, it's useful for bioactive molecules.), catenanes (mechanical bonds), cubanes (cube), 1-methylcyclopropene (used to preserve apples), 2-cyclopropenecarboxylic acid (toxic but is removed by polymerization), prismane and its derivatives (explosive hydrocarbon), Dewar benzene and its derivatives, benzynes, any stable carbon oxides other than carbon monoxide and carbon dioxide (carbon suboxide, mellitic anhydride, ethylenetetracarboxylic dianhydride), pentacyanocyclopentadiene (Superacidity is impressive for a carbon acid with only nitrogens aside from its acidic hydrogen and its carbons. This shows the power of cyano as an electron withdrawing group.), moniliformin and squaric acid (both compounds represent vinylogous analogues of carboxylic acids, the former toxic, the latter, when twice-deprotonated, aromatic), ladderanes, allenes and (especially very long) cumulenes, ketenes (The parent is toxic and is a decomposition product of vitamin E, found in e-cigarette juice, which caused a spike in lung disease in the United States in 2020. The derivatives and their acetals are useful reagents.), azetes (especially of the Figueroa-Valverde type), dithietes, bullvalene, enediynes (chemotheraupetic drugs that are highly mutagenic), [12]helicene, dodecahydroxycyclohexane (stable for a perhydroxyaliphatic - or here, alicyclic - compound), superphane and cyclophanes, o-carborane, decaborane.
Automatic A tier: Bodipy (Boron trifluoride, if hydrolyzed to, is toxic, and will hydrolyze to HF. Bodipy series represent useful ligands.), chlorhexidine (disinfectant), fusafungine (antibiotic), metformine (used to balance glucose levels in type 2 diabetics), 3-methyl-2H-furo[2,3-c]pyran-2-one (karrikinolide, the chemical of smoke), (3a¹s,5a¹s)-3a¹,5a¹-dimethyl-3a¹,5a¹-dihydropyrene (look at that name!), calix(4)arene (useful ligand).
Other molecules that are an automatic S tier from me: Quadricyclane (photoelectricity), olympiadane (created just because), dioxygen difluoride (automatic), chlorine trifluoride (automatic), NanoKid (educational chemical), NanoCar (four buckminsterfullerene derivatives acting as wheels), buckminsterfullerene (room-temperature stable molecular carbon allotrope), cyclo[18]carbon (the chad explosive, consisting of just carbon), the first cyclocarbon to be synthesized, an all-carbon electron acceptor), polyynes (of astrochemical importance, especially long polyynes).
Cursed chemicals are interesting in one way or another. I didn't rate anything below A here.
Note: Quadricyclanes are useful in photochemical heating, not photoelectricity.
You noted, but kind of glossed over that mellitic anhydride is a mineral, meaning it's naturally occurring geologically which is pretty neat imo. There are a decent amount of complex, cursed biochemistry, but not much cursed geology.
Absolutely!
I'm a physicist but I love these videos. I swear you guys have no fear of death in the lab compared to us
Oh, the chemists I knew from University (late 90s) were VERY keen on safety while we physicists were looking for the lost 2W laser beam with a piece of black cardboard with the laser running or cleaning laser active polymers off glassware with dichromic acid ..... Looking back, I'm surprised that nothing happened.
@@wernerviehhauser94 my university is particularly proud of only ever having one postgrad student permanently blind themselves with a laser beam. For the most part we're more of a danger to extremely expensive equipment (laser optics) than to ourselves
There are certainly cursed inorganics as well. Polythiazyl perhaps.
I usually watch chemical force for cursed inorganics
Like out of nowhere he grabs a 30 years old ampoule of some chemical that you won't even think existed
The fact he nonchalantly burns $70 dollars worth of decaborane
Sulfur nitride, sulfur hexafluoride, hydrogen polysulfides, krypton/xenon oxyfluorides, diimine, orthoperiodic acid, diphosphorus tetraiodide, borazine. Most of those are like C tier tho.
I only studied a tiny bit of chemistry and I don't understand anything, I love it
:)
Squaric Acid? Now I finally know what I need to dissolve some stubborn pixels!
1:50 *Because there are a lot of Boron in it, I'm gonna put it in B tier*
Makes sense
"teletubbie nomenclature" is something i never want to hear ever again
Lmao
This seems like an upgrade for people who already know all of these molecules.
I took a year of organic chemistry in college. I was just a math major who liked making potions. And what did I get out of it? Now I can appreciate this video
Hey ! Love your work in general and the tier list series particularly ! Can be inspiring to see those twisted structures, somehow haha.
I can relate for the helicene (M) or (P) enantiomers that they are usually made as racemic mixtures and then separated on a chiral HPLC. I'm working in a group where almost everyone make those.
Different approach here, working in a group making selectively one helicene enantiomer. Racemates are still synthesized for developing chiral LC methods to determine EE, but we can get 98+% of EE with some catalysts, conditions and substituents!
Thanks :)
Id love to hear talk about azidoazide azide. It exploses when you look at it with that much nitrogen in it
Eh it’s not quite that touchy. Explosions and Fire made some and it wasn’t anything crazy, at least in the sensitivity department.
I work with catenanes and rotaxanes, they aren't cursed per se but often pretty Hard to make. Also we make tBu-calixarenes in our introductory o-chem lab, the tBu groups can the be removed by a retro-Friedel Crafts rxn to yield the calixarene shown in your Video, which works quite well
please share the papers in the discord, that sounds really cool!
The most cursed one in my opinion is hexaphenylethan. I dont know why but just looking at it causes me to shiver in fear.
Yeah that does look cursed
I know they're not that cursed, but buckyballs with noble gases trapped inside them are just the funniest things to me. Also, you should include the helium dimer (He2) in an inorganic sequel video.
As a pharmacy student I appreciate the inclusion of metformin
Great career choice. 🤟🏻
I accidentally made an allene once by the reaction of pyrrolidinone with propargylbromide using NaH as a base. The allenyl pyrrolidinone was surprisingly stable. I was also shocked that I could column it without problem.
Yeah - you can usually do those alkylations with just K2CO3 in DMF or K3PO4 in toluene btw (the normal non-allene one)
Enediynes are amongst the most interesting molecules I've read about due to their reactions. There are natural enediynes synthesized by some microorganisms that act as toxins that kill competitors by directly cleaving DNA with biradicals. Whilst I am still skeptical of the claims of their antitumor properties, I definitely think they should be given more attention in microbiology and pharmacology.
Yeah they are pretty cool
I hat to synthesise an Allene as a part of a undergrad lab course, with 3 other students given similar analogues. Even though the synthesis failed for all four it was because of the old, almost completely air oxidised wittig precursor. So instead we hab to hydrolise a Alleen containing ester, which tolerated 4 hours of reflux in 50% Ethanol/Water with NaOH quite well. The alleen for me was 2-benzyl-5,5-dimethylhexa-2,3-dienoic acid hzdrolised from the corresponding ethyl ester.
For the synthesis it was intended to react an acid chloride with stable wittig reagent and according to the supervisor it was usually successful with yields around 50%.
Interesting!
I'm also suprised you showed Catananes and not Rotaxanes or Molecular knots. Olympiadane is ofcourse the most cursed of the catenanes I know.
What
Another very nice and informative presentation. I was happy to see ketenes on the list. My graduate work dealt with the cycloaddition reactions of chlorocycanoketene, used to prepare beta-lactams by cycloaddition reaction to imines.
Awesome! Very cool stuff!
Would love to see more of these, interesting and informative at the same time!
Thank you :)
This is my first time watching one of these videos and I love how it's presented almost exactly like a lecture I'd get with one of my online textbooks
You should probably have pointed out that ladderanes are natural products, which is proper mental
It’s wild!
Wow, this guy could be ranking pokemon for all I know
This video taught me that everyone is naturally cursed by proxy of chemicals.
Lol at the shade against Explosions & Fire for Cubane.
I just watched a molecules tier list... and I love it
thank you :)
How about Adamanzane? It is one of the most visually cursed compounds I've ever seen
Look up Mobius Orbitals - essentially there's an excited state of a pi-conjugated system with only one node, each p-orbital is twisted slowly around the ring.
Why did I read it as morbius orbitals instead of mobius orbitals? I've been looking at too many memes, haven't I?
There's also paddlanes, fenesteranes, kekulenes, polyynes ,halonium ions, twistane and asterane and orthonitrates etc...
dodecahydroxycyclohexane looks like biblically accurate hydroxide
I'm surprised you don't have octaoxygen (red oxygen), that is like cubane on steroids!
That one could go in the cursed inorganic tierlist
@@00bean00 very true, but black nitrogen is pretty neat too
In our class, the molecule we consider the most cursed is 3,3-Diethylpentane which has a structure strikingly similar to swastika sign. In india, since we use the one that is at right angles and it's a holy symbol, it's absolutely no problem in our schools or in public places. But since our class loves dark jokes, we decided to tilt it at an angle of 45° to make it absolutely cursed.....
Explosions and Fire has also struggled with MCP.
as a non chemistry person i would put methyl cyclopropene in s tier. from what you said it sounds pretty cool but to non chemist eyes it looks like a little beaker and i think its cute
SInce you mentioned ketenes and allenes, I would have been curious where you'd rate diazoalkenes :D
Idky, but as a non-chemist “this will trigger you, if you are… like most people” really sent me
This channel gets put in T tier for me, not because your channel name begins with t or anything, simply because your content is terrific
Thank you :)
Helicenes can be formed using different approaches. One strategy is to use alkyne hydroarylation reactions to form the rings. When applying transition metal catalysts, if you use appropriate chiral ligands, you can get enantiomeric excess of up to 98+% for the helicenes. Depending on conditions, catalysts/ligands and the substrate, there are also some side products with interesting optical properties.
In general, helicenes are interesting, but at the same time pretty annoying. As an analytical chemist supporting the organic people's workflow, the tendency to crystallize within hours from nearly any non-chlorinated solvent and then turn into completely insoluble bedrock drives me insane on a daily basis.
Yesss, my boi pentacyanocyclopentadiene! :D
Another cool symmetric ring molecule is Sulflower. Essentially 8 thiophene rings fused side-to-side, forming a flowery ring. Also means the molecule has no hydrogen left. Not sure how cursed you would rate it, but it is definitely an aesthetically pleasing sight!
It’s a pretty cursed molecule
"because it starts with a c we'll put in in the c tier"
Sound logic if I've ever heard it.
Check out Harry Anderson's work (Oxford University), they have made a super cursed giant aromatic wheel and other similarly insane structures
Just googled him, that chemical looks insane! Did they actually make that?
pubs.acs.org/doi/10.1021/jacs.0c05033
16:30 I can't believe you savaged Tom like that
Lol
Not only have I prepared allenes, I have prepared iodo-allenes (via SN2' displacement of the precursor propargyl alcohol with HI/CuI). Somehow, allenyl-X is thermodynamically more stable than propargyl-X. This is not to say allenes are OK. They are not, they are terrible! I was trying to purify a low MW allenyl iodide via distillation (per a lit method) and it exploded the first time I tried. The next time I modified to distill under reduced pressure, and it exploded again. Finally, I distilled 1) under pressure and 2) from dodecane so that it never went dry. At last, no explosion. 0/5 do not recommend allenes.
Haha
16:33
Love the Explosives and Fire nod
I would love an inorganic cursed molecules tier list !
will do!
just mix like a gram or so of all of them in a beaker
How does a molecule become cursed?
Having said that, methyl ethyl ketone peroxide probably falls into the cursed category.
So many exotic looking molecules I'd never have a contact with. And then there's metformin, something I dispensed tens of thousands doses of.
interesting!
If someone synthesized an allene from lignin, would that be called a woody allene?
S-Tier comment
Anything Derek Lowe wrote about in "Things I Won't Work With" is S-tier cursed, no matter the field of chemistry.
do chemists use boron as an insult?
5:55 Well what do you know! I ate a bunch of metformin shortly before watching this video!~
Squaric acid’s name 💯💯💯
You’re correct that it doesn’t contain a carboxylic acid, but it is a double vinylogue of a carboxylic acid (i.e. a double vinylogous acid) meaning that there is a double bond between the OH and the carbonyl - very cool functionality.
I love the term vinylogous
I love how you spent a solid twenty seconds describing hamburgers as cool while rubbing superphane with an audible smile. S-tier content.
are there any pictures of these chemicals? I'd be interested to see what they look like
Molecules can’t really be imaged, they’re too small.
i would love to see a cursed (bio)chemist workplace comments/questions
I think hexamine is cursed enough to be on the list
I liked for the Explosions and fire cubane synthesis dig near the end. :D
You should have had the hexamethylbenzene dication, it can be made from dewar benzene and has a hexavalent carbon forming a pentagonal pyramid.
You can write it as (Cp*-C-Me)²⁺. You heard that right, *methyl(η⁵-pentamethylcyclopentadienyl)-λ⁰-methanediium.* Carbon tries to be like metals in both hexamethylbenzene dication and benzene dication ((Cp-C-H)²⁺), η⁵-cyclopentadienyl-λ⁰-methanediium). (Yes, I used "λ⁰-methanediium" for CH₂²⁺ from which I put the Cp/Cp* group on that carbon.)
@@californium-2526 It's amazing what you can get to stick together when you have the electron density of an aromatic ring and total electron desert everywhere else, at least I think that's a reasonable way to think about it??? And yeah, the naming conventions just kinda break down when you come to hypervalent compounds so go wild.
@@samheasmanwhite I had to use the organometallic nomenclature for the benzene dications.
There's decamethylsilicocene, so, when's the carbocene analogue (with two η⁵-Cp-derived ligands) gonna come out?
@@californium-2526 Hmm, as far as I am aware; Cp*1+ can't contribute less than four electrons so for actual pyramidal bonding that would have to be bonding with a 4+ carbon atom and the bonding orbitals would be really mashed into each other since carbon is so small, so if it was stable it would have to be a coordination complex rather than actual bonding. I found a paper (doi:10.1021/om980737l) that does a computational study and they think the carbon will end up just bonding to one carbon in each ring to make a carbene, or if using Cp instead of Cp* it would form phenylcyclopentadiene, but who knows, maybe it could work :)
What's the lambda notation? I don't know much about this and couldn't find out what it is.
@@samheasmanwhite Lambda notation, used in hypervalent compounds, e.g. organo-hypervalent-halogen compounds, e.g. iodoxybenzoic acid, IBX, phenyl(bis(trifluoroacetoxy)-λ³-iodane; cyclic organophosphorus(V) and organosulfur(IV) or (VI) compounds. IUPAC assumes that elements in these groups will normally have this much bonding available: 4 for group 4a, 3 for groups 3a and 5a, 2 for group 6a, 1 for group 7a and 0 for group 8a. You don't use the lambda notation for that. You go higher or lower than that, and you use the lambda notation (generally, the exceptions involve onium and ate ions that arise from species which had a "normal amount of" bonding, e.g. ammonium, phosphonium, oxonium, sulfonium species; and organoxenon compounds - nobody seems to use "xenane" for such compounds. However, if it arised from a species where the lambda notation was used, you use the lambda notation, e.g. sulfoxonium from a sulfoxide).
Me who never had a business with chem since high school: Hmmm... Interesting.