In my final undergrad Ochem lab we synthesised 2,4,5-triphenylimidazole, and my interest in this particular lab this ended up making me pursue a PhD specialising in photoswitches, so it carries a special place in my heart.
Benzofurans in the tryptamine motif act as if the oxygen were nitrogen (as in indole). Even more interesting is that benzofuran tryptamine derivatives are more potent agonists on selective serotonin sites than their amine counterparts (which seems paradoxical). Following this trend, work with benzofuran derivatives of ibogaine (a tryptamine with a complex ring structure), showed replacement of the amine with oxygen decreased cardiotoxicity, yet remained therapeutically selective and efficacious. This is important as ibogaine is being studied for its potent ant-addictive properties, and that side effect is a severe concern. Not sure about the thio derivative, however.
@@That_Chemist additionally to tryptamines, benzofuran can be used as a backbone for MDMA derivatives that in clinical studies have shown a near-complete elimination in serotonergic neurotoxicity.
For your next tier list, you could rank chemical compounds with unusual or funny names like Moronic acid, Arsole, Fenestrane, Churchane, Cummingtonite, Sulflower or Penguinone. There is a wikipedia article listing many of them: en.wikipedia.org/wiki/List_of_chemical_compounds_with_unusual_names
I'd also add Bromo-DragonFLY to this list ( en.wikipedia.org/wiki/Bromo-DragonFLY ). It's a terrible drug that's more powerful than LSD but lasts for days. Strangely enough, it's not illegal, probably because no one would want to use it recreationally.
Benzofurans are used in a bunch of serotonergic drugs that are similiar to MDMA like 6-APB or 5-MAPB. Wikipedia has a list called "Substituted benzofurans" which lists all of them.
@@likemau5552 especially in combination with a clean stimulant, plus you do the famed supplement routine and you get no comedown or negative after-effects in general. Indeed the benzofurans are maybe the best entactogens out there.
16:50 As a porphyrin chemist, I can't agree that porphyrin is just a ligand for inorganic chemists, an endless amount of wonderful and complex derivatives of this macrocycle were synthesized to the moment :)
My Bachelor's thesis was on 9,10-diboraanthracenes (anthracene, but the carbons in the middle are boron). Now, these are readily reduced by alkali metals, making them aromatic. Turns out, the can reversibly(!) bind hydrogen gas, which is pretty cool.
I've contributed to "TCDD" and created the "2,4,5-Trichlorophenol" wiki page. 2,4,5-TCP self condenses very easily under runaway exothermic reaction directly to TCDD. Excellent inclusion of this class of unwanted ultra dangerous side products that all organic chemists should know about. This type of transparency is important. Cheers.
You should have included naphthyridines. In my opinion these are some of the most neglected heterocycles. I am working on a 2,7naphthyridine derivative currently. I have a love hate relationship, as I think they are super cool, but they are very polar and can be difficult to purify >:| So I'm conflicted if should be A tier for coolness or F tier for difficult purification.
I like how the reasoning covers a spectrum from "it has so many uses, and in fact you wouldn't live without them" to "it starts with a B so it's B tier"
One pretty interesting phenothiazine-containing molecule is clorpromazine, a typical antipsychotic drug, which was developed from promethazine and is considered the very first psychopharmaceutical
Imidazoles deserve s tier I agree, but you as a not-med-chem person ought to love bmim salts!! Butylmethylimidazolium salts are ionic liquids! Useful for processing furans like FDCA (useful as a PET replacement!)
My favourite aromatic heterocycles, based purely on the "coolness" factor, are the metallocycles. Back in an undergrad inorganic course, the prof mentioned platinum's use in organic chemistry, replacing C atoms; Pt⁺⁴ is similar in electronegativity and size to C. That got me wondering if one could use Pt in aromatic structures as well. When my first Ph.D. project got chucked out (as I mentioned before), I suggested looking into that concept. My supervisor did a bit of doodling, then decided that Pt heterocycles wouldn't work out, but that it would be worth looking at the ferroles. (C₄H4₄)Fe₂(CO)₆ has a weird structure in which some of the the COs bridge between the Fe atoms. At any given moment, the (C₄H4₄) is σ-bonded to one of the Fe atoms, and that (C₄H4₄)Fe ring is η⁵ bonded to the other Fe atom; in solution, the (C₄H4₄) flip-flops between the two Fe atoms. In general, the metalloles are clearly not aromatic; among other indicators, the bond lengths in the (C₄H4₄) are clearly C=C-C=C rather than being approximately equal. I was trying to knock off the extra Fe, and find ligands so that the (C₄H4₄)FeRₙ was aromatic. After about 2 years of this, without much success, my supervisor suggested that I'd be better off doing a computational chem project he'd had his eyes on: he wanted me to enhance an existing modelling package to handle things like metallocenes. That project went considerably more smoothly. I found out later that a couple of other groups in other institutions had also been looking at aromatic metallocycles at around the same time, with some success. One was an osmium-based cyclooctatetraene analogue, IIRC. Another that I'm seeing now is "doubly aromatic": two separate delocalized bond rings, one with 6 electrons, the other with 10.
In the organic labs where the solvents lie One heterocycle to rule them all, one heterocycle dumped in the sink One heterocycle bottle left open and raise a nasty stink In the organic labs where the solvents lie
Phenothiazine was also the first anthelminthic (kills parasitic worms in humans and livestock), and is an anaerobic inhibitor of free-radical polymerization (sometimes used for stabilizing acrylic acid). Porphyrins (and the related corrins) are also the base structure of biomolecules besides heme, such as chlorophyll and vitamin B12. They are also found in dyes such as phthalo blue. I have used imidazoles as the core of non-coordinating anions, by adding two equivalents of either tris(pentafluorophenyl) borane or alane. Salts of these anions with alkylammonium cations gave ionic liquids which were miscible with aliphatic hydrocarbons.
I know the more methodology focused videos gain far less views and probably take a lot more research, but are there any plans to continue your (I)OC series with more advanced topics in the near future, besides the monthly recent publication series?
I love how you just come up with rules and explanations for your sometimes quite harsh treatment of motifs. But we all have our opinions. Great video btw! This topic was refreshing, somewhat basic-ish stuff. I enjoyed it. (:
5-(2-methylaminopropyl)benzofuran (abbreviated 5-MAPB) this substance is a violently euphoric stimulant. Other one i remember is bromo-DragonFly which is an extremly dangerous, potent as well as long acting hallucinogen. It works as an serotonin agonist and as an monoamineoxidase inhibitor.
Selenophene chemist here.. *HISS* (The smell isn't too bad actually, but some of its derivatives are horrific. 2-cyanoselenophene 2-iodoselenophene and 3-bromoselenophene are particularly unpleasant.)
Indole chemistry is interesting, as that 3 position is very friendly to substitution and addition; tryptamine, of course, is simply indole with an ethylamine group on the 3…throw a couple methyl groups on the N of the amine and you got N,N-dimethyltryptamine (DMT), or stick an ethyl group on the alpha position to get alpha-ethyltryptamine (AET) which was actually prescribed as an antidepressant called Monase in the 60’s.
Back in grad school, I came up with a way to draw the porphyrin structure by hand very quickly. I would draw the outer ring of the molecule first, then draw the four N's in a square, then add 8 lines to complete the pyrroles. When I'd draw it on the whiteboard, the other students and professors would be stunned. But hey it was part of my research at the time.
Yay!! I love to see two heterocycles I’m using in the undergrad research lab I’m in (benzoxazole and benzisoxszole). Sad to see them low 😢 but tbh I can’t complain about the other rankings!
When I worked in just methods/medchem I also didn't know about indolizine, but now I work in SWIR fluorescent dye synthesis for biological imaging and we use indolizines as electron donors. They are setting records in our field and they're very fluorescent by themselves which is cute :)
Benzofurans are common in pharm, actually they're a substitute for indoles lol (dimemebfe is my favorite name for a drug but it's a benzofuran analog of a tryptamine) or methylenedioxybenzene (5 or 6 MABP come to mind but I'm sure theres plenty)
I work with indazoles, they‘re a pain in the arsole to substitute at the 1H position because the 2H will react as well and it’s not that easy to separate one from the other. I haven’t found a reliable way to get the desired product, for me the base didn’t make a significant difference that I would call it steering the reaction in one way or another. Still for me they deserve S tier because they‘re going to get me my masters degree
Arsole is rather weak in aromaticity, and has arsenic, but it's named arsole, so it's S+. Tetrathiafulvalene, technically an ethenedione tetrathiodiacetal, is important as it helped for the development of molecular electronics, so it's S+ as well. (1,2,4,5-)Tetrazine is explosive and is the main heterocycle of some developed explosives, so it's S+. Tetrazole is similar to tetrazine in that it's explosive and is the main heterocycle of explosives like silver 5-nitrotetrazol-1-ide and sodium 5-azidotetrazol-1-ide, so it's S+ as well. Imidazoles make up the core of imidazolium ionic liquids, so they're S+ as well. Porphyrin is the heterocycle in the ligand of heme, so it's also S+. Purine is the heterocycle of DNA bases, so it's S+ as well. On the contrary, selenophene is F, as it has selenium in it. Dioxins, when fused with two benzene rings, are F- as they're the component of several potent pollutants. Phosphinine is a stable heterobenzene where the heteroatom is on the 3rd period, so it's an A+. Thiophene apparently smells like benzene, so a A+ for not containing a sulfurous smell. Thiophenes as a group are B from me. Furan is a simple aromatic heterocycle, but is carcinogenic and toxic, so D+. In the meanwhile, furans are seen in many parts of chemistry, so they're B+.
My favorite chemistry. Aromatics and Heterocycles. List is obviously almost endless. Arsole - hahaha 😆 2-(benzofuranyl) N,N-Dimethylethanamine. The Oxo analog of DMT active or no? I'd wager it is being the aromatic lipophilic core is retained.
Do n-heterocyclic carbenes count for this list? If so: fantastic properties as ligands, air sensitive as fuck- requires a glovebox or schlenk line, which definitely prevents them from being s tier. Probably A or B tier, depending on your proclivities towards gloveboxes
@@That_Chemist I don’t have a link all I have is an old presentation from Ciba from 1992 , I believe that ICI developed this chemistry for red disperse dyes during the late 1980’s
Indole has to be the best because its stinky cousin can be so informative. Example: years ago I am riding on my bicycle by a Barber shop that advertised 7 dollar haircuts. While in the chair I smell skatole from his fingers. Some of my cut hair falls in my ear cancel and the barber proceeds to clean it out with his little finger. When I get home I rinse that canel with 2% acetic acid to preemptive strike the skatole associated microflora.
No Diazepine ring?? That would've been one for S tier for its commonality in pharmaceuticals. No, I am not asking for it to be added because of Xanax. But diazepine It's a ring and very common in chemistry.
Note on the "pyridine-like" smells: For anyone wondering how Pyridine smells, it smells like trying to dissolve a rotten fish in a mixture of ether and gasoline.
Where are the big long organic semiconductor fluorescent ones? (4+benzine rings, lots of resonant double bonds) Can you do a whole video on molecular electronics?
@@That_Chemistcool, hadn't heard of that one before... Fluorine, figures... Good one .. to go in a funny named compound tier list. If you make a video regarding molecular electronics, besides that, thiophene and tetrathiafulvalene , you don't have to limit yourself to heterocycles and can include anthocene,pentacene etc., Also don't have to be limited to aromatics and can include long chains of conjugated linear resenent pi bonds .. rhodopsin derivatives... I'm sure there's a lot I don't know about that I would like to!
It always bothered me that tetrahydrofuran's name is derived from how it's synthesized from furan, even though it's way more common than furan. It feels like furan should be the one with a name derived from THF.
Its 2-substituted derivatives are quite easy to make in fact, just a simple condensation, reflux in alcohol or acetone (depending on the substrates) overnight. The same is with its cousin imidazopyrimidines. Look it up!
@@chrisboyall8602 yes it's gonna be substituted with more aromatic cycles. I'm making something fluorescent. I don't know the methods name, but there will be 3 steps after I add some Nh3 and NO2 groups to shift the fluorescence colour
Porphyrin syntheses are absolutely cursed. As said in the video, pyrrole (usually necessary for synthesis of porphyrines) is a challenging compound :-) Porphyrins glow nicely under UV-light though.
Indole is weird because at low concentration, it smells good for the odors of some flowers but at high concentration, it smells like shit or bad breath. Personnaly, I was born insensitive to this compounds and can breath high concentration without being disgusted like there is nothing. :)
I may have misheard you but it sounded like you said tetra-azido-tetrazole. Bro regular azotetrozole is a touch explosive that energetics labs won't even handle. That made my ass pucker just hearing it 😬
firstly: this title is amazing. secondly, and i’m saying it again, “arsole” is the best compound name ive ever seen.
thanks!
In my final undergrad Ochem lab we synthesised 2,4,5-triphenylimidazole, and my interest in this particular lab this ended up making me pursue a PhD specialising in photoswitches, so it carries a special place in my heart.
Awesome!
what the hell kinda undergrad lab were you in haha we just synthesized benzocaine and dimedome 😭😭
@@NathanPrice6 It was a 3rd year UG synthetic lab, and at my uni a chem degree only required 2nd year organic chem to graduate.
Benzofurans in the tryptamine motif act as if the oxygen were nitrogen (as in indole). Even more interesting is that benzofuran tryptamine derivatives are more potent agonists on selective serotonin sites than their amine counterparts (which seems paradoxical). Following this trend, work with benzofuran derivatives of ibogaine (a tryptamine with a complex ring structure), showed replacement of the amine with oxygen decreased cardiotoxicity, yet remained therapeutically selective and efficacious. This is important as ibogaine is being studied for its potent ant-addictive properties, and that side effect is a severe concern. Not sure about the thio derivative, however.
Very interesting!
@@That_Chemist additionally to tryptamines, benzofuran can be used as a backbone for MDMA derivatives that in clinical studies have shown a near-complete elimination in serotonergic neurotoxicity.
For your next tier list, you could rank chemical compounds with unusual or funny names like Moronic acid, Arsole, Fenestrane, Churchane, Cummingtonite, Sulflower or Penguinone. There is a wikipedia article listing many of them: en.wikipedia.org/wiki/List_of_chemical_compounds_with_unusual_names
I'd also add Bromo-DragonFLY to this list ( en.wikipedia.org/wiki/Bromo-DragonFLY ). It's a terrible drug that's more powerful than LSD but lasts for days. Strangely enough, it's not illegal, probably because no one would want to use it recreationally.
Urazole thats a nice idea
@@squareacid Hmm. A five-membered ring of which one atom is nitrogen and another is uranium = uranazole?
Uranyl is funny, Skatole is another one as well
@@jpolowin0 5 membered
is right but is a 1,3,4-triazol with 2 carbonylgroups
Benzofurans are used in a bunch of serotonergic drugs that are similiar to MDMA like 6-APB or 5-MAPB.
Wikipedia has a list called "Substituted benzofurans" which lists all of them.
they are also putatively less neurotoxic than their methylenedioxy counterparts
They are also a lot more fun to party on than MDxx's :D
@@likemau5552 especially in combination with a clean stimulant, plus you do the famed supplement routine and you get no comedown or negative after-effects in general. Indeed the benzofurans are maybe the best entactogens out there.
16:50
As a porphyrin chemist, I can't agree that porphyrin is just a ligand for inorganic chemists, an endless amount of wonderful and complex derivatives of this macrocycle were synthesized to the moment :)
My Bachelor's thesis was on 9,10-diboraanthracenes (anthracene, but the carbons in the middle are boron). Now, these are readily reduced by alkali metals, making them aromatic. Turns out, the can reversibly(!) bind hydrogen gas, which is pretty cool.
cool!
Can you show how to synthesize those?
I've contributed to "TCDD" and created the "2,4,5-Trichlorophenol" wiki page. 2,4,5-TCP self condenses very easily under runaway exothermic reaction directly to TCDD. Excellent inclusion of this class of unwanted ultra dangerous side products that all organic chemists should know about. This type of transparency is important. Cheers.
Thank you for your service to mankind
You should have included naphthyridines. In my opinion these are some of the most neglected heterocycles. I am working on a 2,7naphthyridine derivative currently. I have a love hate relationship, as I think they are super cool, but they are very polar and can be difficult to purify >:|
So I'm conflicted if should be A tier for coolness or F tier for difficult purification.
I like how the reasoning covers a spectrum from "it has so many uses, and in fact you wouldn't live without them" to "it starts with a B so it's B tier"
the benzofuran placement got me
flabbergasted fr
Just to put tetrazoles in perspective, "Azidoazide azide" is a tetrazole, at least under standard conditions.
One pretty interesting phenothiazine-containing molecule is clorpromazine, a typical antipsychotic drug, which was developed from promethazine and is considered the very first psychopharmaceutical
very cool
Imidazoles deserve s tier I agree, but you as a not-med-chem person ought to love bmim salts!! Butylmethylimidazolium salts are ionic liquids! Useful for processing furans like FDCA (useful as a PET replacement!)
They’re ok, but they still require some water to be a liquid
@@That_Chemist Depends on the anion. BMIM acetate and bis-triflamide are both anhydrous ionic liquids.
My favourite aromatic heterocycles, based purely on the "coolness" factor, are the metallocycles. Back in an undergrad inorganic course, the prof mentioned platinum's use in organic chemistry, replacing C atoms; Pt⁺⁴ is similar in electronegativity and size to C. That got me wondering if one could use Pt in aromatic structures as well. When my first Ph.D. project got chucked out (as I mentioned before), I suggested looking into that concept. My supervisor did a bit of doodling, then decided that Pt heterocycles wouldn't work out, but that it would be worth looking at the ferroles. (C₄H4₄)Fe₂(CO)₆ has a weird structure in which some of the the COs bridge between the Fe atoms. At any given moment, the (C₄H4₄) is σ-bonded to one of the Fe atoms, and that (C₄H4₄)Fe ring is η⁵ bonded to the other Fe atom; in solution, the (C₄H4₄) flip-flops between the two Fe atoms. In general, the metalloles are clearly not aromatic; among other indicators, the bond lengths in the (C₄H4₄) are clearly C=C-C=C rather than being approximately equal. I was trying to knock off the extra Fe, and find ligands so that the (C₄H4₄)FeRₙ was aromatic.
After about 2 years of this, without much success, my supervisor suggested that I'd be better off doing a computational chem project he'd had his eyes on: he wanted me to enhance an existing modelling package to handle things like metallocenes. That project went considerably more smoothly. I found out later that a couple of other groups in other institutions had also been looking at aromatic metallocycles at around the same time, with some success. One was an osmium-based cyclooctatetraene analogue, IIRC. Another that I'm seeing now is "doubly aromatic": two separate delocalized bond rings, one with 6 electrons, the other with 10.
Ah yes, my favorite chemical - indole, in S tier. Thank you kind sir. Request: An entire video about its derivatives and reactions.
I never yet experienced working with heterocycles. I will be so excited next school year just to beat up my cyclical depression.
Tier list idea: Top chemicals you don't want to work with.
Definitely not inspired by a certain chem blog. Maybe get him as a guest.
bacon Bacon BacoN BaCon BACON Is there somewhere I can order pyrazine by fractions of kilos?
Probably - I would be surprised if Aldrich doesn’t sell it
In the organic labs where the solvents lie
One heterocycle to rule them all, one heterocycle dumped in the sink
One heterocycle bottle left open and raise a nasty stink
In the organic labs where the solvents lie
I think Flubendazole (benzimidazole containing) adequately summarises the last few years
its a pretty molecule - I haven't seen a benzophenone with a benzimidazole before :)
Phenothiazine was also the first anthelminthic (kills parasitic worms in humans and livestock), and is an anaerobic inhibitor of free-radical polymerization (sometimes used for stabilizing acrylic acid). Porphyrins (and the related corrins) are also the base structure of biomolecules besides heme, such as chlorophyll and vitamin B12. They are also found in dyes such as phthalo blue. I have used imidazoles as the core of non-coordinating anions, by adding two equivalents of either tris(pentafluorophenyl) borane or alane. Salts of these anions with alkylammonium cations gave ionic liquids which were miscible with aliphatic hydrocarbons.
Cool!
I know the more methodology focused videos gain far less views and probably take a lot more research, but are there any plans to continue your (I)OC series with more advanced topics in the near future, besides the monthly recent publication series?
I might try and make them patreon goals at some point - I just need to figure out how to structure it
I do TTF research chemistry and I was very delighted to see your rating!
I think the methods chemists will revolutionize the field with TTFs
I love how you just come up with rules and explanations for your sometimes quite harsh treatment of motifs. But we all have our opinions.
Great video btw! This topic was refreshing, somewhat basic-ish stuff. I enjoyed it. (:
Also bacon sucks. It's just nauseatingly greasy and salty. You know while eating it that it really isn't good for your health. 😅
salt and oil is actually good for you - now I'm not as sure about the preservatives tho
but don't be mean to bacon >:(
5-(2-methylaminopropyl)benzofuran (abbreviated 5-MAPB) this substance is a violently euphoric stimulant.
Other one i remember is bromo-DragonFly which is an extremly dangerous, potent as well as long acting hallucinogen. It works as an serotonin agonist and as an monoamineoxidase inhibitor.
Selenophene chemist here.. *HISS*
(The smell isn't too bad actually, but some of its derivatives are horrific. 2-cyanoselenophene 2-iodoselenophene and 3-bromoselenophene are particularly unpleasant.)
Indole chemistry is interesting, as that 3 position is very friendly to substitution and addition; tryptamine, of course, is simply indole with an ethylamine group on the 3…throw a couple methyl groups on the N of the amine and you got N,N-dimethyltryptamine (DMT), or stick an ethyl group on the alpha position to get alpha-ethyltryptamine (AET) which was actually prescribed as an antidepressant called Monase in the 60’s.
Back in grad school, I came up with a way to draw the porphyrin structure by hand very quickly. I would draw the outer ring of the molecule first, then draw the four N's in a square, then add 8 lines to complete the pyrroles. When I'd draw it on the whiteboard, the other students and professors would be stunned. But hey it was part of my research at the time.
Yay!! I love to see two heterocycles I’m using in the undergrad research lab I’m in (benzoxazole and benzisoxszole). Sad to see them low 😢 but tbh I can’t complain about the other rankings!
:)
When I worked in just methods/medchem I also didn't know about indolizine, but now I work in SWIR fluorescent dye synthesis for biological imaging and we use indolizines as electron donors. They are setting records in our field and they're very fluorescent by themselves which is cute :)
Awesome!
Benzofurans are common in pharm, actually they're a substitute for indoles lol (dimemebfe is my favorite name for a drug but it's a benzofuran analog of a tryptamine) or methylenedioxybenzene (5 or 6 MABP come to mind but I'm sure theres plenty)
I've heard 5 MAPB is quite the research chemical
@@kashjpm2272 5mapb is pretty fun yes
@@caphunterx2322 never tried it did try some nice stim rcs tho
I work with indazoles, they‘re a pain in the arsole to substitute at the 1H position because the 2H will react as well and it’s not that easy to separate one from the other. I haven’t found a reliable way to get the desired product, for me the base didn’t make a significant difference that I would call it steering the reaction in one way or another. Still for me they deserve S tier because they‘re going to get me my masters degree
DM me on Discord - I can give you advice (if you don't want to, just use K2CO3 like I was saying)
Definitely rate indazoles. I've made some 3-aminoindazoles from 2-fluorobenzonitriles, really nice chemistry aside from the need for hydrazine.
Hydrazine is too damn useful to be so toxic.
Arsole is rather weak in aromaticity, and has arsenic, but it's named arsole, so it's S+.
Tetrathiafulvalene, technically an ethenedione tetrathiodiacetal, is important as it helped for the development of molecular electronics, so it's S+ as well.
(1,2,4,5-)Tetrazine is explosive and is the main heterocycle of some developed explosives, so it's S+.
Tetrazole is similar to tetrazine in that it's explosive and is the main heterocycle of explosives like silver 5-nitrotetrazol-1-ide and sodium 5-azidotetrazol-1-ide, so it's S+ as well.
Imidazoles make up the core of imidazolium ionic liquids, so they're S+ as well.
Porphyrin is the heterocycle in the ligand of heme, so it's also S+.
Purine is the heterocycle of DNA bases, so it's S+ as well.
On the contrary, selenophene is F, as it has selenium in it.
Dioxins, when fused with two benzene rings, are F- as they're the component of several potent pollutants.
Phosphinine is a stable heterobenzene where the heteroatom is on the 3rd period, so it's an A+.
Thiophene apparently smells like benzene, so a A+ for not containing a sulfurous smell. Thiophenes as a group are B from me.
Furan is a simple aromatic heterocycle, but is carcinogenic and toxic, so D+. In the meanwhile, furans are seen in many parts of chemistry, so they're B+.
6-APB was a very neat benzofuran in my experience ;^)
A-tier for Ambien. Can’t remember why, but it feels right.
“Pyridine-like” is my new favorite euphemism.
Bacon, also at 17:15 true, wise words are spoken
Tier list on the strongest carcinogens when.
Alt Title: Which Aromatic Heterocycle is the One Ring who rule them all
My favorite chemistry. Aromatics and Heterocycles. List is obviously almost endless. Arsole - hahaha 😆
2-(benzofuranyl) N,N-Dimethylethanamine. The Oxo analog of DMT active or no? I'd wager it is being the aromatic lipophilic core is retained.
Substituted benzofurans are fascinating too; especially in the world of investigating non-neurotoxic alternatives to MDMA. 6-APB is an incredible drug
I’m curious to see which drugs will see FDA approval
You should do a tier list on the worst chemicals to work with
Do n-heterocyclic carbenes count for this list? If so: fantastic properties as ligands, air sensitive as fuck- requires a glovebox or schlenk line, which definitely prevents them from being s tier. Probably A or B tier, depending on your proclivities towards gloveboxes
Pyridine is highly used to understand the nature of zeolite catalysts, namely their bronsted to Lewis acid ratio
Not just maple syrup, but evil maple syrup! The kind Satan has on his waffles.
I would never ever eat benzisoxazole
Our aromatic heterocycles will make your Harley Davidson smell great, brother!
o-phenanthroline makes a nice fluorescent compound with ruthenium chloride.
yes it does - I made it once
Arsole will forever live rent free in my mind.
I love how half of these rankings were made by fun anecdotes rather than logic like you did for the other half lol
that's the best part of this channel
remarkable means that you can remark on it
the whole family of heterocycles after pyrrole are all hilarious: phosphole arsole stibole bismole moscole???
9:45 I'm studying caffeine right now 👀
You forgot pyrrolo[2,3-d]pyrimidine and pyrrolo[3,2-d]pyrimidine ( 7 and 9 deazapurines).
You missed the Arsole fused to a benzene ring, Benzarsole!
Make a tier list of how easely molecules are to dissolve!
Yeah that’s hard to think of as a tier list video - I could definitely do “least soluble molecules tierlist though”
@@That_Chemist yeah, that makes more sense
Benzofuranans are used in the dyestuff industry particualrly in Disperse dyes used to dye Polyester fibres
If you wanna share a link to a paper ill check it out in the replies
@@That_Chemist I don’t have a link all I have is an old presentation from Ciba from 1992 , I believe that ICI developed this chemistry for red disperse dyes during the late 1980’s
Ferrocene grups are used in organometallic chem as phenyl phosphine analogss. NOT equivalent to Cyclopentadiene.
Iron is a "hetero" atom. Very stable metallorganics undergo standard aromatic reactions.
Guaiazulene (aromatic 10e-; 5 ring fused to 7 ring) is aromatic yet chemistry is hetero to Naphthalene.
yeah I had azulenes on here but someone in the discord was critical of all carbon heterocycles
Indole has to be the best because its stinky cousin can be so informative. Example: years ago I am riding on my bicycle by a Barber shop that advertised 7 dollar haircuts. While in the chair I smell skatole from his fingers. Some of my cut hair falls in my ear cancel and the barber proceeds to clean it out with his little finger. When I get home I rinse that canel with 2% acetic acid to preemptive strike the skatole associated microflora.
Indole is my favourite, the backbone of serotonin, melatonin and a whole load of psychedelic drugs
Do you know if "The Portable Chemist's Consultant" available in pdf format or print? Sadly do not have an ipad :
I don't know of anyone who was able to find it as a PDF, but it would be really nice if they made one...
When I think of benzofurans I think of the entire class of stimulants/entactogens/psychodelics that's sold in the grey market. Have fun!
No Diazepine ring?? That would've been one for S tier for its commonality in pharmaceuticals. No, I am not asking for it to be added because of Xanax. But diazepine It's a ring and very common in chemistry.
Note on the "pyridine-like" smells: For anyone wondering how Pyridine smells, it smells like trying to dissolve a rotten fish in a mixture of ether and gasoline.
actually yeah that is true
Cmon man if you put purine in S tier pyrimidine gotta be there as well
Where are the big long organic semiconductor fluorescent ones? (4+benzine rings, lots of resonant double bonds)
Can you do a whole video on molecular electronics?
srry BODIPYs
@@That_Chemistcool, hadn't heard of that one before... Fluorine, figures... Good one .. to go in a funny named compound tier list.
If you make a video regarding molecular electronics, besides that, thiophene and tetrathiafulvalene , you don't have to limit yourself to heterocycles and can include anthocene,pentacene etc., Also don't have to be limited to aromatics and can include long chains of conjugated linear resenent pi bonds .. rhodopsin derivatives...
I'm sure there's a lot I don't know about that I would like to!
you forgot pthalazine and quinoxaline
It always bothered me that tetrahydrofuran's name is derived from how it's synthesized from furan, even though it's way more common than furan. It feels like furan should be the one with a name derived from THF.
Don't tease me with that benzthiazole, it's the foundation of my research! S-tier all the way smh
Imidzolopyridine looks hard to make.
Its 2-substituted derivatives are quite easy to make in fact, just a simple condensation, reflux in alcohol or acetone (depending on the substrates) overnight. The same is with its cousin imidazopyrimidines. Look it up!
Important to say- Furan doesnt undergo a DA rxn due to its aromaticity. The energy in breaking aromaticity is too high and the product isn’t favored.
yes it does - look up its reactions with maleic anhydride
rt, and the product ppts from the reaction
Arsole is aromatic and a ring. This is all.
Oooh, porphyrin, I am gonna be making that
Meso-substituted by any chance? And if so, Lindsey synthesis Or Adler-Longo? Very interesting molecules!
@@chrisboyall8602 yes it's gonna be substituted with more aromatic cycles. I'm making something fluorescent. I don't know the methods name, but there will be 3 steps after I add some Nh3 and NO2 groups to shift the fluorescence colour
Porphyrin syntheses are absolutely cursed. As said in the video, pyrrole (usually necessary for synthesis of porphyrines) is a challenging compound :-) Porphyrins glow nicely under UV-light though.
@@skuul666 and they're giving it to a poor master student and telling him to find papers on the synthesis pathway himself ;.;
Is there any way to isolate indole, specifically 2-oxindole? I have had it as an impurity for months and cannot get it out!
sublimation?
Furan = Cupcake molecule
And Guiazulene is a pretty blue color. Found in Germanium oil so "G" tier?
Er, geranium the flower.
haha
Where is heptazine?
Indole is the best because its the base of my favorite substances 😇
Indole is weird because at low concentration, it smells good for the odors of some flowers but at high concentration, it smells like shit or bad breath. Personnaly, I was born insensitive to this compounds and can breath high concentration without being disgusted like there is nothing. :)
its also weird because sometimes it hits more like naphthalene
Borazine? I would find it kewl to include a carbon-free compound.
No triazine?
Cool looking compound🤣
I must have accidentally deleted it :(
this blew my mind
no mans sky much
Not the tier list we asked for, but the tier list we needed
I may have misheard you but it sounded like you said tetra-azido-tetrazole. Bro regular azotetrozole is a touch explosive that energetics labs won't even handle. That made my ass pucker just hearing it 😬
I would say indol
Lord of the Rings time ! Isn’t there any toilet break?
fun fact - you can watch this whole video from the toilet if you choose to do so
What about coumarins? :(
fml
Personally suggest furazans.
Ooh, why do you say so? I'm always looking for new chemistry!
As a highschool student I'm just happy to be included (´ . .̫ . `)
:)
6:51
Things will never be the same. D:
F
Arsole is A because Arsenic. That one is so obvious.
If I'm being pedantic, dioxins shouldn't be in this video as they aren't aromatic ... 8 pi electrons so anti-aromatic!
its actually non-aromatic
Greetings from Germany!
Guten Tag
How is porphyrin inorganic
It’s used in inorganic complexes
Thiophene based nucleosides!!!!!
BACON!
Literally just took a Phenothiazine containing drug, it was delicious. With that I can say goodnight yall!
i have to disagree on bacon, salmon is the best meat, bacon's pretty close tho
smoked salmon is ok, but salmon still doesn't come close to bacon
Bacon!
pyrroles gave me depression. F tier.