Welcome back. I'm That Chemist.
And today we're going to be deciding which molecules are the most cursed.
So the rules for today
are that the molecules that go in this list must be somewhat organic.
If you guys are interested,
I can do a cursed inorganic molecule tier list in the future,
and we're going to be ranking molecules based on how cursed they look
and maybe how cursed they are, but probably for the most part just based on looks.
So without further ado, let's get started.
Let's pick a nice easy one like squaric acid.
So squaric acid is called an acid because, you know, despite how it looks lacking
any specific carboxylic acid groups, it's a relatively acidic acid
now it's a square and it's a square
with quite a lot of double bonds, which is kind of interesting.
I think square acid is pretty cool looking,
but it's not cursed when we start looking at some of the other ones in this list.
So Squaric Acid might have some applications,
especially as it has analogs such as squaramides.
But I think we're going to have to
put squaric acid in D-tier because it's relatively simple.
Now, if we look at some other
interesting ones like decaborane, you might be saying, hey, that's not cool.
Why are you putting decaborane in there?
That's not even organic.
And I want to include decaborane because it's a little bit easier to see
before we get to carboranes.
So decaborane,
you can see they have more bonds than boron compounds typically have.
We start getting to this crazy situation where we can have a boron
bound to five other borons or other substituents,
and this will trigger you if you're like most people.
So decaborane is a little bit controversial,
can be used as rocket fuel on its own.
It's not too interesting, but once we start
converting them to things like carboranes, they get a little bit more interesting.
But it is still relatively cursed because it's got just so many bonds
to each boron and it just kind of breaks your traditional chemistry knowledge.
So because there's a lot of boron and I'm going to put it in B-tier.
Now, since we're talking about boron, let's talk about carboranes.
So carborane is this interesting icosahedron.
You can see there's two little black dots shown on the left, one here.
All of the unlabeled
atoms are actually borons in this case where normally we don't label carbons,
but in this case we're not labeling the borons. Just for clarity.
You can see it's a little bit challenging to draw carboranes and this is what's known
as ortho carborane because these two carbons are side by side.
If we moved one of the carbons
to one of the lower positions, then we would have meta- or para- carborane.
So these have some interest as analogs that could be used in drug design.
So it's possible
to install some new units at either some of the borons or some of the carbons.
And it's been recently a hot area for method development.
Although while this looks like something super unpredictable
and unstable, this is actually still a relatively greasy molecule.
So this could be useful for some chemical applications.
Additionally, you can see where the borons are cursed
because they're connected to so many different
other borons and carbons, the carbons are actually the same.
So you can see these are pentavalent carbons
and once you start adding substituents, it gets even worse.
So car brains are a little bit more cursed than decaborane in my opinion,
because they also start violating
carbon to an extent.
So I think we're going to have to put carboranes in S-tier.
Now another really cursed molecule is bullvalene.
So if you've never seen bullvalene before,
it's actually a fluxional molecule, which means that in an NMR timescale
this is actually rearranging back and forth all the time
and the cyclopropane can reform on the opposite side of the molecule
and the double bonds will migrate so bullvalene relatively
cursed molecule I'd like to see what would happen if one of you proposed
that as a possible scaffold for drug design and just see what
see what your superiors have to say.
Definitely one of the most cursed molecules
because it's fluxional and it's breaking carbon carbon single bonds all the time.
Now, one that's kind of close to home for me is dithietes.
So dithietes
are this interesting four membered ring where we still have a double bond as well.
And sometimes if you have a 1,2- di thiocarbonyl compound,
you'll actually form dithietes.
And so I've inadvertently at one point in time made a dithiete
derived from an alpha keto amide which then ended up forming this dithiete.
They're relatively few and far between, but they're a very interesting molecule.
However, they're still relatively boring.
So I think we're going to have to put them in E-tier.
Now, one that is extremely cursed is Dewar benzene,
and this is one possible structure that Dewar originally proposed
as the possible structure for benzene, although this has actually been made
subsequently. So this can be synthesized.
I don't think it has any real utility,
but it definitely is a very cursed looking molecule because not only does it
have two cyclobutane rings, but there's also a double bond
making them cyclobutenes.
So this is definitely pretty cursed
I think Dewar
benzene is going to have to go in a tier now in a similar vein is ladderanes
and it turns out that you can make polymers of cis- or trans- ladderanes.
And so you can see here, this is one where we have we have a trans orientation,
although you could imagine a cis one would kind of start
wrapping around like a series of squares, just wrapping together.
So polymers of these have been made and they have some interesting properties
that you don't get from your typical molecules.
Now I personally think bladder aids are also quite cursed,
so I think they belong in a tier. Now,
A really cool one that I really like is cyclophanes.
And so among the cyclophanes, I've included this one called Super
Superphane, which has an ethylene group connecting every single substituent
of the benzene ring.
And I think this is just one of the coolest looking molecules ever.
This is like a hamburger of a molecule, superphane, definitely S-tier.
It's maybe not as cursed as some of the other ones,
but it is one of the coolest looking molecules here.
It's just like that.
All that electron density between the two benzene rings is just set up.
So it's exactly like a burger.
Great, great, great molecule.
Okay, metformin.
Metformin has this interesting motif where we can see there's a lot of nitrogen
in a row.
To me, as a synthetic chemist, this is reminiscent of Boc anydride,
although we've just replaced all of the oxygens with nitrogens.
This is used as a diabetes medication, which is quite interesting.
And after we're done with metformin, we're also going to talk about
chlorhexidine, which you might be more familiar with.
So compared to some of the other ones here,
I think it's a little bit less cursed, but it is still pretty cursed.
So I think we can put it in D-tier.
Now, chlorhexidine is a common antiseptic that's used in,
you know, a lot of applications where you need to like sanitize the skin.
So for instance, if you're going to donate blood
or if you're going to get a shot, usually they sanitize your skin
with chlorhexidine.
And while I heard it being used several times and I've personally had
it used on my skin when donating blood or getting vaccines,
I was surprised to find out that this is the actual structure
because I had never seen anything like this in my time in organic chemistry.
So definitely a cursed molecule because it has two of them.
I think we could probably put it in, C-tier,
plus there's chlorine in there. So that makes sense.
Now azetes, azetes are a particularly unstable class of molecules.
If you've never seen an azete before, you might be interested
in checking out the video that I did on Figueroa.
Figueroa is a fan of azetes.
It's doing his cycle additions between alkynes and acetonitrile,
which are a little bit outlandish,
if you ask me now, azetes start with an A and they're extremely unstable.
So I think they definitely belong in A-tier.
Now, one that might look a little bit boring
or a little bit cursed to you is methyl cyclo propene.
So methyl cyclo propene, you're probably thinking this isn't a molecule
anyone really works with.
This has no application, but it's actually used as an antagonist
for the receptor that binds for ethylene in plant ripening.
And so this just goes in and it prevents molecules or prevents
ethylene molecules from getting in and signaling the plant to start ripening.
And so for the transportation of fruit and other vegetables,
this gas is actually often used to keep stuff from ripening.
And if you're interested, I can make a video on this in the future.
Definitely a really interesting molecule and I think it's underappreciated
in the organic chemistry community.
Super cool, relatively simple though.
I think this probably also belongs in D-tier because it isn't that cursed.
Now, one that is definitely curious is dodeca hydroxy cyclohexane.
So if you were to just take cyclohexane and put a ketone on every single position,
it will just totally hydrate to this gem-diol on every single ketone.
So this is definitely a relatively cursed molecule.
I immediately would wonder what this tastes like because it
looks like it would be pretty sweet as well as like pretty unstable.
So I'm going to put this in B-tier.
Now another analog of benzene is prismane so prismane is also C6H6
although it can be explosive at room temperature.
This was one of the initial structures
proposed for benzene, although it was found out
to be much less stable than benzene, as you might expect.
And seeing this type of structure where we have three cyclobutanes
fused together, forming cyclopropane is extremely cursed.
And I think this definitely belongs in S-tier. Now enediynes
enediynes are present
in some natural products, it can be used as like a warhead because this could do
a cycle of addition to generate new ring as well as a di-radical species.
Definitely quite an interesting class of molecules,
although their synthesis
is relatively straightforward through a cross coupling reaction.
So not too too cursed.
Definitely interesting,
but because it starts with an E,
I think we're going to have to put it in E tier
Bodipys; Bodipy based fluorescent dyes have seen a lot of
presence in literature over the past decade or so,
and it seems like every week you're seeing another paper in JACS
where people have made some new analogs
and they looked at what happened when they added substituents at various
positions to the fluorescence
based on the absorption of these molecules.
So definitely really cool; worth looking at if you've never come across them before,
although they aren't that cursed They look slightly.
cursed but I'd say they could probably go in D-tier. Carbon suboxide.
You'll look at carbon suboxide and go, what the heck, that can't be real,
but it is real.
And apparently
it's actually used as an intermediate for the synthesis of malonate derivatives.
So you can imagine adding in like ethanol or water to this and this is like a ketene
and so a nucleophile will add at the carbonyl
and then the proton can go to the middle one and you could actually get diethyl
malonate from this.
So this is actually really cursed in my opinion.
I think that's way too many double bonds in a row.
And I think carbon suboxide
is definitely S-tier, which is appropriate as it's a SUB-oxide.
Now similar to carbon suboxide are the cumulenes.
And so cumulenes are when you just have like a poly allene.
So here's an allene, here's a ketene and here's a cumulene
before we go to the cumulenes, maybe let's
actually just talk about ketenes so ketenes can be formed.
If we have something like an acyl halide with an alpha proton,
that could be protonated, although you can synthesize these through other means.
The parent compound
ketene is an extremely toxic gas, but it's really useful industrially
as you can add nucleophiles to that like
super super easily. Now really toxic although they are synthetically useful.
And you can also do cycloaddition chemistry to these
such as dichloroketene.
So useful but a little bit cursed.
I think we're going to have to rank them lower than carbon suboxide.
So I think we can put ketenes in maybe C tier.
Now allenes in my opinion are even more cursed. Now,
I've seen reports in papers
where people have even been able to make cyclic allenes and column them (a common purification technique; flash column chromotography).
Now if you've worked with allenes and they're relatively stable,
I want you to comment down below because I am skeptical about allenes,
although I've seen people work with even cumulenes
and they've said that they could column those and I'm just skeptical.
So I think allenes are a little bit cursed.
I'm, going to put them in B-tier and cumulenes are going to have to go right to S-tier.
It's also worth noting that there's some groups that have made cyclic allenes
and they've checked
how big the ring size can be before the allene
or before the cumulenes are no longer stable.
So they'll have just a lot of double bonds in a row like this, like a cumulene
rather than a poly-ene.
And then they just cyclize it back around to see how stable they are.
So definitely an interesting molecule.
Now ethylene tetracarboxylic dianhydride.
I don't personally think this molecule has too many synthetic applications
other than someone wanted to see if they could make it and they did.
I bet this would be really good for Diels
Alder reactions, as this is super electron deficient alkene,
definitely somewhat cursed-looking, although it does have five
membered rings going for it, which stabilizes it a little bit.
It also starts with an E, so I think we can put it in E-tier. Now,
Pentacyanocyclopentadiene is definitely a cursed molecule, if not for the fact
that it's a cyclopentadiene that's penta substituted.
You'll be interested to know that the pKa of that C-H,
which is protonated in this case is actually -11.
So it's a super acid.
And when it's formed,
when you form this compound, it's actually synthesized as the sodium salt.
So not a very happy molecule, definitely wants to have that negative
charged, fully de-localized into all of those nitriles.
So I think this is pretty cool looking
and since it's a super acid, it gets a little bit more street cred.
So I think we're going to have to put it in A-tier.
Now there's benzynes.
Benzynes are really useful intermediates, especially if you want to do
cycloaddition chemistry.
I personally have made several different benzynes in my time in the lab
and you can do a lot of interesting chemistry with them.
Now the issue is sometimes to generate these, you're using anthranilic acids
through the diazonium, intermediate - diazonium carboxylates.
These can often be explosive as well as the benzynes being relatively unstable.
You can't isolate them in most cases.
Usually they're just prepared in situ, but you can do some cool chemistry.
So benzyne.
Benzynes are pretty curse
because you're forcing the geometry of that triple bond to be no longer linear.
I think benzynes belong in A-tier
now. catenanes.
catenanes are among the more cursed structures that chemists have made.
And so essentially
you can see here they have a long chain and two molecules are just interlocked.
So this is kind of like two links on a chain.
Now, how you selectively form links on a chain is beyond me,
although I believe materials scientists have found ways to do this
definitely interesting molecules and it would be cool
to see what properties you can get once you start covalently
closing rings in the presence of other rings.
Super cool and I'm interested about these just as a topic.
So let's change gears a little bit and let's look at moniliformin.
This looks a little bit like square acid, although this is actually
a fungal toxin that is produced by certain fungi.
And this is an interesting toxin that we're going to be covering
in an upcoming video.
And it's a little bit more cursed than squaric acid, in my opinion, because you've
somehow got rid of one of the oxygens, but you still have all these carbons
there. Definitely interesting overall though, and I think it belongs in C tier.
Now Helicenes - we have one member in the Discord
whose dissertation focused on the synthesis of Helicene analogs.
You can see they're kind of cool.
They're like spiral cut, like curly fries kind of cool.
They could have some interesting
physical properties and optical properties that people want to study.
Now I look at these and I wonder, can you selectively synthesize one curve?
Or when you make these, do you get mixtures?
It's not clear to me
if you know, you can comment down below and I'd be interested to know about that.
I think these are really cursed,
especially based on how awful their NMR spectra look
based on what I've seen in the discord.
So I think they belong at least in A-tier. Now fusafungine
fusafungine is actually an antibiotic which is used
in some applications such as like in nose sprays and whatnot.
But this also looks a little bit like
the siderophores, although the the nitrogens have been methylated.
So this could still be a good ligand, but it looks like kind of a cursed version
of a siderophore I think this probably belongs in B-tier.
Now Calixarenes are these interesting systems
where it might not be clear by looking at this,
but all of these hydroxy groups are pointing right up
and these can be used in a host guest interactions
so they can study the properties of these when they're interacting with some
sort of guest, which could be a metal, something that interacts with the oxygens.
These are definitely cursed-looking,
especially if you look up the structure of these in 3D online.
Very challenging to synthesize in my opinion, just based on
the geometry of this molecule.
Definitely pretty cursed, but because it starts with the C, we'll put it in C tier.
Now, mellitic anhydride is a derivative
of this interesting mineral where instead of having this anhydride, you just have
benzene with six carboxylic acid groups.
And so all that was done here is they've just dehydrated this to this
tris-anhydride, which I think is really interesting and really beautiful.
And it looks kind of like the an-
hydrides are just like jumping for joy, sticking their arms out.
Now, this is just five and six membered ring, so it's still relatively stable,
but it is definitely a cool looking molecule in my estimation.
Now, Cubanes.
Cubanes are an interesting class of molecules, although other members
of the chemistry community have struggled to synthesize them in a timely matter.
But maybe there's good reasons for that.
It's interesting to note that these are promising as scaffolds
for medicinal chemistry.
So you can imagine this is pretty greasy.
This is a little bit bulky.
You could use this as an analog for benzene potentially.
I also didn't mention this about the cyclophanes earlier with the superphane,
but cyclophanes also have promise to maybe make analogs in drug design
so you could have substituents off of two different parts of the cyclophane
and that might mimic a benzene. That's kind of cool.
It'll be interesting to see what drugs get developed with that in the future.
But Cubanes are similar now.
Cubanes have been around for a while. They're starting to be
commercially available, so maybe they're not that cursed.
But I think Cubane still has a place in all of our hearts.
I think Cubane probably belongs in C-tier.
This interesting molecule here is used as a seed germination inducer,
and this is found in smoky water, smoke water.
So interesting plant hormone.
You can see this has
got a six membered ring, which is... it's not quite benzene.
We've got an oxygen there.
So it's kind of like a pyranone
almost; definitely an interesting looking molecule.
I would be concerned about doing chemistry on this as it looks fairly sensitive.
So I think I'm going to put this in D-tier.
But when we compare it to many of the other ones
we're talking about, there's definitely more cursed molecules.
Now, this interesting carboxylic acid, if you haven't seen this before,
is what I coined Tinky Winkenic acid or triangulenic acid.
Although somebody brought to my attention
that triangulene is actually the name for another molecule.
So I think we're going to have to default to the Teletubby nomenclature
as is more appropriate.
If you haven't seen the the Mushroom mycotoxin video
featuring this carboxylic acid, I'll include a link to that here.
Now, this has a three membered ring with a double bond.
That's pretty cursed,
but I don't think it's any morecursed than methyl cyclopropane.
So I think we could put this in D-tier,
although it starts with a C, so we'll put it in C tier.
Now, similar to cubane and cyclophanes, we have BCPs - bicyclopentanes
and analogs of this are frequently made using [1.1.1]propellane
and this has been an especially hot area of chemistry recently
as people have figured out various different ways to functionalize
[1.1.1]propellane into pharmaceutically useful building blocks.
So [1.1.1]propellane, in my opinion, is super duper cursed.
Look at that strain, right?
Three cyclopropanes, all fused together, one
carbon carbon, single bond and it's so cursed that it opens to BCP.
So BCP once opened seems relatively stable.
There's some other reasons you might want this instead of a cubane
for drug design, definitely a cool looking molecule overall.
So this last one here is this dialkyl substituted pyrene.
And so the interesting thing about these
is these could be used as molecular switches
because when these are oxidized or reduced, they're able to pop open
that single single bond, carbon, carbon,
single bond right in the middle there into an open form and a closed form.
And so this could be useful for the design of molecular machines,
although you look at this system and it is no longer planar
and it is not happy that you took all of its planarity away from it.
So this probably belongs in A-tier.
So hopefully this has been an
entertaining video about cursed chemistry because we haven't put anything in F-tier.
I think we're going to move Bodipy down to F-tier because it has fluorine in it.
And with that, I hope you have a great day.