Figuerouhhh... finds a way

In this video, I discuss YET ANOTHER Figueroa paper. This time he manages to make really strained rings using ninhydrin, substituting TWO nitro groups.
/ thatchemist
Community Discord - / discord
----------------------------------------------------------------------------------------------------------------------------------
Links to articles discussed in this episode:
Sketchy Paper - www.doi.org/10...
Ninhydrin review - www.doi.org/10...
Selenium paper - www.doi.org/10...
----------------------------------------------------------------------------------------------------------------------------------

[@FishNChipsor]

The low boiling point of DMSO can be explained by the low atmospheric pressure at the altitudes where Figeroa operates.

[@oleksandrmykhalchenko1079]

Figueroa may be devil or god, so it explains it.

[@davideaezakmi9530]

Would that count as "special conditions" though?

[@That_Chemist]

True!!!!

[@FishNChipsor]

that would also explain why he found the mass spec at 679.25. Thats the lab number where the spectrometer is. 679th story, room 25.

[@TheBackyardChemist]

Clearly he is suffering from hypoxia. He must be.

[@the6p4c]

"The mass spectrum was found" - well it certainly wasn't actually measured

[@notthatcreativewithnames]

I feel a bit confused for someone from Mexico to publish an article in the Chemistry Journal of Moldova.

[@That_Chemist]

100%

[@grock9211]

It seems that there is some low quallity national journals that scientists use to boost their numbers

[@penteractgaming]

This is often done with papers that were rejected from journals that would make more sense or that they know would be rejected.

[@shinybreloom4027]

Moldova corruption index

[@jackhinkley6162]

Actually (Chem J) Mold says a lot about the quality of the reported chemistry and the paper. I have nothing against the journal or Moldova. Both are trying their best under difficult conditions.

[@Ater_Swe]

I have worked with DMSO that boiled at 120 C. That was during my stay as an exchange student at the base on the dark side of the moon from the documentary Iron Sky! We worked outside since they did not really have any fume hoods.

[@That_Chemist]

the atmosphere is nature's bin

[@Ater_Swe]

@@That_Chemist Yes and especially on the moon. What have the moon animals done for us? So I say F them moon bears.

[@Ater_Swe]

And if people don't get my reference. :) kzbin.info/www/bejne/gKXLZax3idOciZY

[@PlanckRelic]

I'm not sure if TC is casually quoting some E&F esoterica or if this is just something all chemists say🤔

[@NoShotTwoKill]

@@PlanckRelic It most definitely is a reference to E&F Only E&F would dare to use the athmosphere to dispose of carbon-tet

[@defenestrated23]

Figueroa is the chemistry equivalent of those ragebait Tiktoks which people "make" wireless headphones by cutting the cable of wired headphones and hotgluing aluminum foil to the ends.

[@ohdangitsroby]

Hi, I work in Figueroa's lab and have worked with dmso that boils at 120°C. You see we keep our entire lab under vacuum. It makes life hard but we manage. /s

[@That_Chemist]

the succ lab has many up and coming researchers

[@lysander3262]

@@That_Chemist bruuuuuuuh 😆

[@samblackstone3400]

@@That_Chemist I tried getting an internship there but during the interview process my eyes started to boil so they rejected me. Only the best of the best can cut it in a lab with such an intense culture.

[@FarragoTheFox]

Reading through these kind of papers must be simultaneously amusing, frustrating, and exhausting. Thanks for your work, this is great content

[@That_Chemist]

The mechanisms give me physical pain

[@FarragoTheFox]

@@That_Chemist I get it. The benzyne to cumulene shit at 10:21 had me in a mild coma

[@27.minhquangvo76]

I thought step 2 of the mechanism at 10:58 was a homolytic cleavage, which brings me closer to dying. 😂😂😂😂 However, in some textbooks, benzyne shows up as a diradical.

[@189643478]

The problem with you young guys is you have no patience. Figueroa rotavaps off his DMSO at room temp in about a week or so… In his next paper he’s going to teach you how to rotavap off an ionic liquid at room temp!

[@jackhinkley6162]

Well I am not immortal and I think that anyone under 20yrs of age trying this method would have retired long before the evaporation was done. Besides a rotovap operates best under a reduced pressure which cannot be provided by mouth suction.

[@mathiasdaniels651]

It is possible to remove DMSO with a rotavapor. You just need a rotavap with a dry ice condensor and a really good pump. I have done it a few times and I know several people who did it regularly (funny enough they work on ionic liquids, a lot of their reactions are just mix two compounds in DMSO, stir it for a week and then remove the solvent).

[@189643478]

I’m not denying the feasibility of rotavapping off DMSO, just saying it will be painfully slow. I once left a beaker of DMSO in the fume hood and weeks/months later it had evaporated completely…

[@mathiasdaniels651]

@@189643478 No worries, I was just giving some extra information just in case people were interested. In theory you should be able to evaporate anything (that doesn't decompose), you just need the right equipment.

[@willemkauffeld7679]

The rotavaping DMSO isn't really that crazy. He is working (so he says) on only 5 mL so that wouldn't take that long. Except if you are in the lab where I'm now where no pump will go under 70 mbar.

[@BenMurphy-go2ks]

One thing I don’t think anyone said in the Discord was how the alkyne is drawn like a vinyl group. Figueroa is truly light years ahead.

[@That_Chemist]

Who says alkynes need to be linear

[@NoLongerBreathedIn]

@@That_Chemist No-one who's worked with cyclooctyne.

[@jogandsp]

@@That_Chemist the same idiots that thought allenes couldn't be part of a six member ring

[@jackhinkley6162]

Benzyne? Cyclohexyne is a stretch

[@jogandsp]

@@jackhinkley6162 but the whole thing about benzyne is that it has significant diradical character because of its constrained geometry.

[@changingyoutubeusernameisn7302]

I've seen bands in an NMR, although that was as an undergrad assaying some hydrophobic nightmare tar I'd made. Everybody had to have a spectra for their lab report, regardless of what horrible contaminated slurry we'd managed to produce up to that point and needless to say the poor machine emitted some of the weirdest noise I've ever seen.

[@samiraperi467]

You *saw* the noise? o.O

[@changingyoutubeusernameisn7302]

@@samiraperi467 In information theory, noise is just entropy in a readout, the information equivalent of waste heat. So there can be graphical as well as auditory noise.

[@mikko-pekkaleppanen3761]

Oh god, those bond angles. That "mechanism"... I have no idea what to say about it

[@That_Chemist]

Figueroas brain is like a vending machine that rips your dollar bill when you try to retrieve it from the machine

[@Vracaum]

Kinda disappointed you didn't showed us the Figueroa spontaneous chloride elimination mechanism

[@elnombre91]

During my PhD I used [Ru(dmso)4Cl2] as a Ru precursor for making complexes of my diphosphorus ligand. Removing the 4 equivalents of dmso from the crude product required heating the flask to 80C under high vacuum for ~2 days. Painful. 10:15 - that'd be a cyclic cumulene. So cursed.

[@jogandsp]

I think the only time I've seen a chemistry drawing that was worse than these was when a TA friend of mine showed me that a gen chem student drew chlorine with seven bonds and a lone pair lmao.

[@yuriikovalov84]

It was proposed in comments already, but I think those toxic series could be very useful to teach students how to write articles. When I began my first year in uni, our task was to write a small article about concentrations of NO2 in air in our city. Even though we were told how to do that, I felt we were taught by principle "throw him in water and he'll learn how to swim" I would be so happy if I saw your videos back then. By critisizing other people's paper I personally see what is better to do and what not to do in a research paper.

[@SMPKarma]

yeah, writing scientific papers is not at all intuitive for someone who hasn't done it before. My supervisor (and co-author) showed me how to write my first couple papers. I both saw how it's supposed to be done and didn't have to come up with my own ridiculous ways of doing it. That should be standard. Students shouldn't be tasked with writing papers they have no idea how to actually write.

[@ruairidhdavidson288]

At this point these folks must be trolling. Even shit like dodgy chemdraw structures, it's not hard to do them properly

[@davidreznick9902]

In our undergrad research safety video they had to remind us that if you spill an acid or base on yourself, you need to show and not neutralize it. Some girl got like 2nd or even 3rd degree thermal burns needing a skin graft from trying to instinctily neutralize a concentrated sulfuric acid spill on her legs with caustic.

[@That_Chemist]

:(

[@elvingearmasterirma7241]

Yeeesh I hope she is doing better now

[@silizimon1293]

It would be very interesting seeing you review a good paper / what makes a good paper in your opinion

[@lukusridley]

I appreciate that the final author has the surname Borges; he would have appreciated the idea of writing papers about fictional molecules

[@bushhawk5460]

This probably is to a chemist as showing an IPv4 number going over 255 is to an IT person.

[@defenestrated23]

I went from chemistry to programming. This is spot on. It breaks your brain and has you yelling "that's not how any of this works!" at the screen.

[@Andy-wc5xw]

Somebody needs to give Figueroa a time machine, his spectra would fit in much nicer in the 1970s

[@8bits59]

legitimate language quirk here: when Figueroa refers to "bands" in an NMR he could be referring to groups of peaks (doublets, triplets, etc.) Since NMR is an RF spectrum, this is actually correct terminology for groups of those peaks or signals outside of the chemistry world. As a ham radio op the way I understand NMR to work is that you're viewing a spectrum of a sideband of a very tiny amplitude-modulated signal, where the amplitude modulation comes from the beat frequencies created by the proton spin alignment and relaxation in the compound under test relative to the RF carrier the "magnet" (which is really a supercooled radio transmitter with a mag loop, but I digress) blasts at it. It doesn't surprise me that someone who appears to be very not a chemist *and* potentially ESL that he would refer to these signals as bands, since outside the chemistry and analytical world that's what it would be called. Not that any of this justifies his absolutely terrible NMRs, though. :P

[@That_Chemist]

he is definitely very not a chemist

[@htomerif]

So I'm gonna go out on a limb here and disagree, though I could be wrong. In radio communications, usually a band refers to an alteration to the carrier frequency by the modulation. For example, with AM radio you might have a channel bandwidth of 10kHz (being, say, voice modulated). While the channel is in use (i.e. being modulated) and you look at it with a spectrum analyzer, it will show a "peak" that is a broad swath covering a 10kHz band. With NMR, there is no modulation. There's just resonance. You sweep the excitation coil (orthogonal to the primary magnetic field) through the expected range of possible chemical shifts and you listen for a resonant response with a sense coil. Its like an AM radio transmitting a carrier with no modulation. There are no bands, just a single frequency (per chemical shift). What you're really doing with NMR is slowly sweeping the carrier through the expected range of frequencies of chemical shifts for 1H or 13C and listening for resonance. Here's the thing. I'm gonna guess you have at least an SDR or something. and when you look at a software spectrum analyzer, you see a thick patch around the carrier. That's legitimately a band. With NMR, you *never ever* want a squishy, wide band of noise. You want peaks and only peaks. Its all carriers and no modulation. The chemical shift is also not dual sideband with respect to the reference, so for a 1H NMR of a substance, you won't see symmetrical peaks on the other side of the reference frequency. As for what you end up seeing, a practical example might be 1H NMR of benzene. On a 300MHz (for 1H) NMR machine and with the 1H benzene chemical shift of 7.3 ppm, you'd get an actual precessional shift of about 2.2kHz, so 300.0022MHz would be what you're looking for for 1H for benzene with a 300MHz magnet. So the whole reason I said all of this was to demonstrate that Figueroa is not (or definitely shouldn't be, if he is) talking about actual frequency bands in NMR. Clusters of peaks are just that: clusters of peaks. The only sane thing you could talk about as a "band" would be the entire space of chemical shifts for 1H or 13C or whatever, in which case that information would be assumed in the context of NMR and no one should actually say it, ever. I repeated some things a few times and tried to give examples. As you can probably guess, I come from a pretty extensive radio background. I'm guessing most of what I said you already know. If you already knew all of it then hopefully someone else finds it useful.

[@jackismname]

You lost me at sideband

[@Zappygunshot]

I think the 'special conditions' Figueroa mentioned must involve running it through a turbo encabulator. The use of modial interaction of magneto-reluctance and capacitive directance in its malleable logarithmic casing - which surmounts the base plate of prefamulated amulate in such a way that the two sperving bearings were in a direct line with the panametric pham - allows it to achieve extreme efficiency in the operation of novertruneons. As the reaction clearly requires a forescent score motion, Figueroa most likely would have paired it with a drawn reciprocation dinglearm, to reduce soinusoidal replanaration. I'll admit I'm not an expert on the specifics of inverse reactive current and its use in unilateral phase detractors, but even an amateur enthusiast like myself could tell you that the turbo encabulator's capability to automatically synchronise cardinal grameters would likely make it an excellent tool in producing the kinds of reactions Figueroa describes in his paper. It's going to be pretty pricey to peer review, as the turbo encabulator alone used to already cost a neat $750,000,000 before the presently turbulent econometroscopic climate wreaked havoc on the transverse polycentrophilic ground fungler market, so manufacturing costs of components like the panendermic semiboloid slots - for fitting the lotusoid-delta type main winding to the stator - will have skyrocketed by now. However, I'm sure you could find a generous enough sponsor willing to fund this kind of research, as it is clearly vital for the betterment of humankind.

[@That_Chemist]

S-Tier shitpost

[@jeroenpunt748]

Like the series! But wouldn't it be (more) interesting to point out the flaws in a paper that is less obviously trash? I am curious to the more subtle ways in which authors might cover up or overhype their results.

[@That_Chemist]

if you have some papers with good examples, please send them my way :)

[@matiastripaldi406]

@@That_Chemist I don't have the reference handy, but I remember in a uni course they showed us a fluorescence (intensity vs wavelength) spectra that had been actually published in a paper, and you could see that they hadn't calibrated the device so the signal between like 270-300 nm (the important part, it was a protein spectra) was completely saturated, a flat line, and all the author's analysis were based on that spectra. And yet it got published, makes you wonder how many wrong papers get printed in general

[@jeroenpunt748]

​@@That_Chemist I mainly know examples from chemical biology papers such as playing around with the intensity/contrast of pictures, cropping of gels or using outrageous concentrations that make the experiments irrelevant. There are no real chemistry examples that I know of, but I could imagine that authors fail to explain impurities in their final compounds that will compromise their subsequent biological tests with that substance. Now that I think about it, such a commentary would be interesting for people of that particular field but not neccesarily entertaining for a broad youtube series 😅

[@chevalierangela]

@@That_Chemist Here is one in Org Lett. Not such a great mechanism?! 😬 Org. Lett. 2022, 23, 18, 7028-7032

[@bradfjord]

I am learning a lot about chemistry through your channel eg. This video taught me exactly how to crucify a First Author Of 157 Papers

[@That_Chemist]

Just you wait - I’m nowhere close to done with him

[@That_Chemist]

I have big things planned

[@bradfjord]

@@That_Chemist can't wait for the Moldovan Cold Fusion episode!!

[@davidtetard5781]

To be fair, a catalyst does not have to be less than 1 equ. For example if it's easily poisoned. The catalyst increases the rate of reaction, that's it. The fact that the Se reagent is consumed (incorporated in the product) shows it's not a catalyst.

[@Sinnistering]

Your toxic series has made me wonder if this is a brilliant way to show people how to read and digest research papers in a pedogogical context. Start with an amusing lecture that shows a terrible paper (with contrast from a good one to demonstrate good vs bad), and then assign an intentionally fun homework or project where the students tear apart another terrible paper. While it wouldn't directly teach students how to gather info (which parts to read closely, which to skim, etc.), it would help indirectly as they go through bad papers and contrast it with what's being done in good papers. It could even be done for high school students, and it could be followed by actual assignments where they need to read scientific papers to help reinforce the concepts.

[@ethang1848]

As a soon to be PhD student myself, a video analyzing the structures of papers and breaking down the critical information and take aways would be lovely!

[@bonbonpony]

It surely is a great series, and I'm definitely archiving in for the future in which I'm able to understand all the stuff being said, because as of right now, I'm not at that level yet. So I'm not sure about the educative aspect of it, unless one explains each piece in simpler words and provide more background details. (Dr. Campbell is good at explaining scientific papers to ordinary people, and translating all the medical jargon to plain English, so maybe some inspiration could be taken from there?)

[@Scrizati]

We had pretty much this exact class in our PhD skills and researcher development program

[@SMPKarma]

@@bonbonpony maybe I'm misunderstanding what you guys are saying, but in order to read organic chemistry papers you need to understand organic chemistry. You need at least a few years of actual synthesis experience to be able to spot bullshit in the procedures. A lot of it isn't in textbooks, so it really does require actual experience. so with that said, that type of a series would only be applicable to chemists. Or is that what you meant? (because to me it seemed like OP meant for the series to be used by the general population, which won't work for reasons stated above)

[@Sinnistering]

@@SMPKarma I don't necessarily think you can do this for a purely general population thing, but I do think making critical reading a more important part of the educational process would be better. For example, here's a thing you can notice in this paper, but it applies to ALL papers: What the hell does he mean when he says "special conditions"? It is a nonspecific statement that doesn't actually give any information. But also you can give examples of more specific details, and even if the example isn't useful generally, the technique can be applied. Like how chemical properties aren't well listed and the authors make mistakes with them. It's specialized chemistry knowledge to spot those mistakes, but it shows how you should be reading to make sure the authors aren't making any stupid mistakes with very basic information. But more importantly, this is enjoyable. It's not just the boring but important work of reading papers, it gives an accessible way of teaching these techniques to a wider and, most notably, younger audience. If you can engage 11 and 12 year olds even just for a bit to get them introduced to this topic, it would be super helpful to getting them used to doing research in undergrad or even in high school.

[@kingnotail3838]

I have taken DMSO off on a rotavap before - I had a decent vac pump and turned the water bath up to boiling!

[@justanotherdude2165]

One can also simply use a lyophilizer. at 0.03 mbar DMSO disappears quite nicely. It does take quite a while though.

[@gmcenroe]

We had a chemist in our lab who used to turn her rotovap batch up to 100C . One day I asked her if she was cooking rice. She was not very happy with me,

[@luca-jminecraftxx9960]

Using Antoine equation I determined that the vapor pressure of DMSO at room temp is about 0.0437865 bar so Figueroa needs a pupm capable of reducing the atmospheric pressure by at least 23 times to be able to remove it without heating

[@jackhinkley6162]

Figueroa's lab is located at the summit of Mt Everest.

[@BlurbFish]

Your calculations lead you to the conclusion that DMSO would *boil* at room temperature if subjected to a reduced pressure of 43 mbar. Time for a sanity check: What pressures can a rotovap be expected to reach? What pressures can a hard vacuum line be expected to reach? Have you ever seen DMSO *boil* in either setup?

[@Glass-vf8il]

I have zero Chem background and 80% of this goes over my head, but I sounds like you’re having a great time. so that’s nice.

[@tyr9514]

I have no idea how you find these terrible papers but it makes me nervous that one day I will do a quick glance through a paper for the numbers/processes I need only to be bamboozled by bad chemistry

[@christiannorf1680]

That's why the first thing to check is where the paper was published

[@eggplantlover6662]

Technically you can draw multiple resonance structures for the benzyne, assuming it stays aromatic. So while it looks cursed, his cyclic cumulene structure is not really wrong IMO. I might start drawing my benzynes this way to mess with ppl.

[@lindseydejesus1877]

obsessed with this series btw. sharing this with my lab

[@That_Chemist]

Thanks for sharing!!

[@Pepecigar]

To think i make nightmare for labeling a NMR peak wrong in 1 spectrum and this guy is just 4 parallel universe above

[@That_Chemist]

Oh absolutely

[@mattescooper5958]

5:00 regarding boiling point -->yeah thats easy: a) take 10 year old DMSO bottle that was open for the same time or b) just add like 80 vol% water. Come on @ That Chemist, you could have figured that out on your own ;) holy mother.... I just watched the entire video. Now lets just leave the fact aside, that any Bachelorstudent would fail any exam drawing (really any) of those mechanism for any professor (except the author). BUT: what are those spectra in the end??? this looks either like a molecule prediction on MestreNova (well ok, not quite because of those multiplets from 1-2ppm not being completely symmetrical) or using the forbidden feature of deleting any noise. Never saw such smooth baseline. How on earth did this pass the "experts" review and got submission?

[@uiucchemistry2664]

These papers I swear make my head mega hurtz lol. Also, looking at Figueroa’s mechanisms, structures, reactions/schemes & NMR spectra is like looking at abstract/interpretive “art” in a museum and trying to guess WTF you’re looking at and why anyone would ever display/pay for such things or in this analogy “publish” such things. What I really want to know is does anyone actually cite his papers? If the “Cited By” section shows legit papers from legit journals citing his work, I’d be severely disappointed in the chemistry community for allowing such bs lmao.

[@DatsuJSB]

Imagine there is a parallel world, where Figueroa's chemistry is well-appreciated, and Ochem that we know well is considered as toxic. That's my hypothesis of these publications.

[@yuriikovalov84]

Yea, actually we are just pathetic humans. Figueroa travelled across universes already, studying their laws. Now he provides us with his wisdom. However, we are not mature enough to appreciate it. Instead, we are rejecting it. The only issue is shitty spectra he records. Literally in every universe.

[@DatsuJSB]

@@yuriikovalov84 maybe he sees peaks that we don't see. Those peaks are in form of waves beyond electromagnetic, traveling through aether actually.

[@colombanoalessandro]

Yeah, that’s the universe where carrots reductions give you the other enantioner

[@californium-2526]

@@colombanoalessandro And it's the universe where unripe banana water gives 100% yield.

[@gustavojordao4400]

I really like this series lol, it makes me laugh a lot. Figueroa, a man ahead of his time

[@B_u_L_i]

Thank you for the efforts! Your toxic series is actually helping me write my thesis by showing me how to not do science and scientific writing while also being very entertaining :D.

[@maxmuenchow]

That guy must have a special supplier for his K2CO3 and MeCN for it to do those bonkers reactions

[@oskr105]

I'm really dispointed that some of the other authors are listed as faculty in otherwise reputable universities in Mexico (as "Francisco Diaz" from the Instituto Politécnico Nacional).

[@mikko-pekkaleppanen3761]

I am starting to think that these are actually written by AI predictive text generator after feeding it several low quality papers from low impact journals

[@petevenuti7355]

that's what I said about the banana paper... makes me wonder which is worse the training data or the predictive text model.

[@Kualinar]

As I said before, Figueroa is doing the paper equivalent of a Gish gallop. Pretty much all of his arrows should show «magic happens» as a process or «magic» as a catalyst.

[@That_Chemist]

the secret ingredient is lying

[@benruniko]

Figueroa is such an idea guy. So many ideas. No reality, but lots of ideas.

[@Zenzicubic]

The secret to boiling DMSO at 120C and below is that Figueroa has his undergrads try to outcompete vacuum pumps, and because of Figueroa's infinite power they are able to do this without their lungs collapsing.

[@That_Chemist]

Haha

[@That_Chemist]

The winner gets the title *The Iron Lung*

[@TheMrFrukt]

My favourite series! Nice. Been waiting all week

[@That_Chemist]

Glad you enjoyed it :)

[@NikitkaDreamer]

cpd. 6 is even more cursed than if the benzene it has had just the boat conformation

[@FueledByKass]

Pulling up an all-nighter to finish TA duties while listening to these videos. Mamma mia, chef's kiss.

[@SuperMuddyPuddle]

Figueroa papers read like an undergraduate lab report

[@Nate580]

As an Undergraduate in chemistry I'm offended by this.

[@SMPKarma]

I think I lost half my IQ looking at those reaction mechanisms. Just... wow. On the upside, maybe now I'm (un)qualified enough to join Figeroa's team!

[@That_Chemist]

Same tbh

[@danielaustin7643]

have you considered that his DMSO might boil at 120 C because he is at a very high altitude, probably with his head in the clouds or even on a different planet?

[@yuriikovalov84]

In previous video I assumed that temperature in their lab is close to 0 K. Therefore pressure there is really small (or absent) because all atmospheric gases is solidified on the floor

[@johnmcclane4430]

It's concerning that he and his colleagues are publishing in medical and medchem journals as well.

[@That_Chemist]

Yeah

[@HuyDucPhan]

I think we also should not waste our time considering these predatory journal 😂

[@blackheadization]

We have a rotavapor connected to a very strong pump to evaporate DMSO in our lab. But it is still a pain in the ass to remove it completely and generally takes a lot of time even for small volumes.

[@jgottula]

Whoa whoa whoa, hold up! In the past (using the passive voice and being as vague as possible about who I was, or what I was actually doing, or whether it even happened), some “2+2” math was done-and this next part may surprise you- *not even requiring special conditions!* I have elementary school teachers that can absolutely corroborate this, and I could cite to them. But, because I am a lazy academic fraud, I will instead simply continue using the passive voice and just say vague junk such as “studies were performed”, “math homework papers were written”, “tests were graded”, “some report cards have shown”, etc.

[@jgottula]

“Additionally, for several years, some calculators were used to show that some arithmetic was correct”

[@jgottula]

Ah crap, I should have said “some integers” shouldn’t I? 🙁

[@californium-2526]

The DMSO flask is at a reduced pressure. Or perhaps it's just that Figueroa-Valverde is at a very high altitude. Nitro leaving group, ninhydrin -OH nucleophilicity, the strained resorcinol derivative. What's the ring strain on that derivative? At least 25 kcal/mol. The cyclohexa-1,3,4,5-tetraene intermediate, the vague "special" conditions, the impossible side product of 4,6-bis(3-ethynylphenyl)amino-1,3-dinitrobenzene. This "research" paper is a literal curse upon chemistry.

[@1temppart201]

I have about zero chem knowledge to like tear apart things any further but I feel like Cl- leaving behind a carboanion isn't really like logically sound

[@hydrogenbond7303]

From now on, I'm using Figeroa instead of fake or bs "His research is such a Figeroa." "This guy is so Figeroa"

[@TheBackyardChemist]

Chem. J. *Mold* he should have used ergosterol

[@That_Chemist]

Lmao

[@alex15295]

The alkyne bond angle 🥴

[@jackhinkley6162]

Another magical treatise describing use of reagents and reactions in magical ways The Sorcerer's Apprentice has a name and may have been promoted to Sorcerer. . His thesis defense, if he did one, was probably quite interesting. Do not fault this journal it very likely operates under difficult conditions with limited funds and cannot do peer reviews.

[@colombanoalessandro]

First!! Im in quarantine with covid and was really looking forward to this :D :D

[@FarragoTheFox]

Hope you get well soon

[@That_Chemist]

Make sure you drink lots of unripe banana water

[@pmathewizard]

Get well soon,

[@theunknown4834]

@@That_Chemist The carrot was a nice surprise though :>

[@colombanoalessandro]

@@pmathewizard cheers

[@mathiasdaniels651]

There are some examples of vicarious nucleophilic substitution reactions where a hydrogen on a nitrobenzene gets substituted, but I'm not sure if it would be possible to do this kind of reaction on dinitrobenzenes. You can have a look at the work from Mieczysław Mąkosza if you want to know more.

[@Zappygunshot]

Before watching this, I had heard of the name Figueroa somewhere before so I clicked. Turns out, I know of him because his malpractice is so hilarious it was considered worth talking about by some internet people. Nice. P.S. don't ask me to find where I got it from, I couldn't remember for the life of me.

[@armanjumakov8918]

Just the fact that he drew fish hook arrows for ionic reactions drives me insane 😂. I guess he’s unaware of radical chemistry 🤷‍♂️

[@hernangabrielastudillocamp6615]

Me siento agradecido de no apedillarme Figueroa. Jajaja. Wild commentary in spanish, just here. Don't try to be Figueroa's, please 🙏🏽 porfi.

[@simedinson984]

i have had nmr samples that i needed to reclaim from dmso it usualy requires alot of will and heat gun use while on the rotavap also a splash guard can be very handy

[@DerWahreTee]

I don't know if you have noticed but I looked into other papers of him and the purification after their synthesis is almost always done with "crystallization using the methanol:water:hexane (3:1:1) system" which is a bit weird considering the wide variety in polarity of all the compounds he allgedly produced. Also does this even result in an homogeneous solution as far as I know MeOH and H2O should both form a biphasic mixture with hexanes. And recrystallizing from a biphasic mixture would certainly be interesting.

[@jeremymcadams7743]

So...what does DMSO do at high temps with NaOH?

[@adrianhenle]

Decomposes, potentially violently.

[@Peaserist]

the reply wont load I am curious enough to try it I have a camping stove, about 50mL of dmso, a lot of KOH, and a decent amount of reckless curiosity

[@pk_xiv2856]

@@Peaserist as 'not remotely a chemist', I'd like to know as well! Be careful tho

[@brandonwatson883]

DMSO, DMF, dmac are terrible to use with bases at high T. A lot of gas evolution from decomp. CO, CO2, ch4, etc. It has ruptured bomb flasks.

[@jeremymcadams7743]

@@brandonwatson883 so it's all strong bases not just NaH?

[@gabotron94]

First was nopal-based everything. Then I discovered our national Polytechnic has a homeopathy school. Then Figueroa strikes. I can see why our (real) science is hard to get out.

[@Jimbreh]

Story time: i had in fact removed DMF(153℃) under 75℃ and reduced pressure. Used a whole lot of toluene to form an azeotrope(not too well). It was all because my TBS-4-hydroxy-l-proline was not soluble in organic layer and I was stupid enough to not just collect aqueous layer and do a recrystallization. Got a lot of shyt from my prof for that. Had a tunnel vision of removing DMF under reduced pressure. Edit: there were still DMF peaks on my NMR spectrA

[@That_Chemist]

Yeah :(

[@1temppart201]

also may I ask why refluxing DMSO for long is a bad idea again? I asked a couple of my chemist friends about it and they agree it's not really recommended but some reactions do use it

[@That_Chemist]

It degrades/decomposes, especially under basic or acidic conditions. In general, we avoid high temperatures like 190 in organic chemistry because lots of molecules start decomposing

[@1temppart201]

@@That_Chemist aww thank you ^^

[@1temppart201]

@@That_Chemist what would be the decomp product? I'd almost guess the sulfone? also what's the mechanism behind its decomp and its acceleration by acid/base I do see that sulfur being kinda nucleophilic but that's where my chem knowledge ends tbh

[@afernandesrp]

Silly question from someone who never published in Organic Chemistry. Do most journals publish possible mechanisms without any actual data on the intermediates being formed? His articles always pull mechanism out of his 🍑.

[@Seorful]

It's not unusual to have no real data for the intermediates since sometimes they simply can not be isolated. But it is very unusual to propose a mechanism without having done at least some mechanistic studies to check for the obvious ways the mechanism could be disproven. The funny thing about mechanism is that they can never be proven to be true just disproven.

[@aldenconsolver3428]

water-methanol-hexane yep, thats one you give a mean drunk when you're the bartender. Mixed with a cheap bottom-shelf whiskey to kill the taste.

[@NormReitzel]

Have you never been familiarized with "candle Chemistry" ? Yoy stasrt by putting 5 black candles (ninhydrin) in a pentagram, then you draw a transmutation circle around them. Then the reactants go in the middle, without special conditions and you speak the transmutation invocation above them. you then remove the dmso at 175°C and 10^-15 bar for 2^10 hours and presto, you can find the 300Hz 13CNMR taped to the wall. Obviously.

[@makylemur7019]

What about publishing in Transnistria?

[@mevnesldau8408]

or donetsk people repiblic

[@midi5581]

This must be some AI engine training in writing papers :D

[@kalamatej]

you can remove readily dmso by freeze-drying at room temperature. although I have used it only on a mL scale

[@kalamatej]

...actually it is not a proper freeze-drying. I have just used the machine for that purpose. 😊

[@alastairdurie7323]

Compound 5 could possibly form from 4, via an ONSH (oxidation nucleophilic substitution of hydrogen) reaction with oxygen as the oxidant. 1,3-Dintrobenzene are susceptible to these reactions, but usually are not the easily reactions to optimise. See the work of Mieczysław Mąkosza.

[@alastairdurie7323]

10 to 12 could be better explained by a related reaction called a VNS (vicarious nucleophilic substitution), would also necessitate the use of base, but again a tricky reaction to control and that aromatic ring is nowhere near electrophilic enough for that reaction to occur.

[@sootikins]

Figueroa's Uni is easily found on Google Maps and is viewable on street view. Looks like a top ranked institution of higher learning (snark! snark!).

[@LCST3002]

La universidad tiene sus carencias como en todas las universidades de mexico, pero digamos que todos tienen una opinión sobre figue, pero por cuestiones legales no debería decir más

[@illiago135]

It's kinda possible to remove DMSO under vacuum, but it's not an activity that I'd like to participate in. Once I had to remove pyridine from a product, and it took an entire day even at the temp of about 100C and 0.01mm Hg. But if you have a particularly useless undergrad student to control the process for a week or so (though it seems more like a month with no heating)... Yeah, why not?

[@OpenChem1]

You just don't understand. These authors are trolling the modern science.

[@dalethomasdewitt]

The world's library was trolled into a commercial wasteland. Publishing stuck in a Gutenberg model of IP remains adamant money is this way. Meanwhile people still die and learn in heaven instead. Regardless it's great to be systematically nervous.

[@ministryoftruth557]

Figueroa for Nobel Prize of Chemistry 2022!

[@bonbonpony]

01:08 Yeah, reading this paper Hertz my brain ;J 09:32 Well, he Figuerouh'd out a way :J 10:16 Hahah I can really hear the pain in your voice :) 12:58 At this point, I'm surprised he didn't produce gold :q 17:32 Let me guess: it xplodes? 18:36 Maybe that's the problem? We were all using brand new reagents instead of used ones? :J 18:40 Yeah, like… m3ntal conditions perhaps?

[@urimiles4371]

I actually have removed DMSO under reduced pressure (high vac, overnight)

[@NuclearFalcon146]

This was somehow funny to watch even though my understanding is limited as a physics major who got a D in high-school chemistry.

[@dreamtheateriano95]

Keywords: Some, Several, Special, Conditions...

[@jofatzxxr4182]

That such a thing can make it into a journal ... You should fire him and all of the reviewers instantly ... And then 150 of those publications. that's just stunning -.- But it is very funny content!

[@raaamonguerra]

It’s funny how he reports the NMR spectra. No integrals? No expansions? 🤦🏻‍♂️

[@avaviel]

Do they get money for these? What's the incentive to make them?

[@That_Chemist]

Research grant money

[@tylerswanson6358]

Hey at least, for the mechanism, he didn’t have the arrow coming from the proton…

[@pmathewizard]

Remember kids quantum mechanics is not magic, oops wrong channel

[@levtrot3041]

Will the IOC series continue ?I realize that topics from now on will have to get more and more esoteric but there's still a lot to cover, like you definitely have topics to make vids about

[@That_Chemist]

Yes, but as long as I do daily uploads, it’s almost impossible to manage making them

[@leo.simensen]

1:58 I heard "...so Figueroa was a mistake in here" rather than "mistaken here", and honestly that's not inaccurate, all things considered.

[@acetophenone820]

Bro that thumbnail gave me anxiety from how disgusting that mechanism is. I feel like I've been GOATSE'd for the first time again

[@nybotheveg]

I've removed DMSO on rotovap. It sucked, but I did it.

[@That_Chemist]

🙃

[@한수씨]

You're being way to harsh! At least in scheme 8 the negative charge attacked the positive and not the other way around this time.

[@JustinKoenigSilica]

lemme just uhhhh introduce two random chemicals by numbers and not names in the ABSTRACT

[@Destroyer249]

Bro im not even a Bachelor of Chemical Engineering i had Basic Organic Chemistry I lectures and i see this clusterfuck at 17:33 from a mile away... How do you break a Carbon Doublebond and have the Hydrogen appear there... Is this some type of Science shitpost? are his papers a benchmark test they give to the new Editors to check that they find any and all mistakes? like some exam? "Ok this is another one from the Figueroa guy. We know it has tons of mistakes, but you only get full points on the test if you can find all of them. you have 120 minutes, go"

[@That_Chemist]

It’s definitely a combination of predatory journals and lack of due diligence on their part

[@justsayin...1158]

Figueroa's works feel less like those of a chemist and more like those of a detective. The way he "finds" spectra, like clues to solve his case, the way he isn't afraid to propose nigh impsossible mechanisms, is reminiscent of the quote from Sherlock Holmes "Once you eliminate the impossible, whatever remains, no matter how improbable, must be the truth." He deduces, what others are too afraid to deduce. And most importantly since all of his cases are unique, all of them have special conditions, which to him makes them non-special conditions. This definitely isn't science, this is art.

[@That_Chemist]

He’s real too - I have video of him

[@That_Chemist]

Coming soon - stay tuned ;)