Tris(2 aminoethyl)amine Puns

We report a facile and efficient two‐step synthetic route for p‐substituted tris(2‐pyridylmethyl)amine (TPMA) ligands to form Cu complexes with the highest activity in Atom Transfer Radical Polymerization (ATRP) to‐date. The synthetic procedure followed a divergent approach, where the p‐Cl substituents in tris(4‐chloro‐2‐pyridylmethyl)amine (TPMA3Cl) were replaced in one‐step and high yield by electron‐donating cyclic amines (pyrrolidine (TPMAPYR), piperidine (TPMAPIP), and morpholine (TPMAMOR)) via nucleophilic aromatic substitution. The [CuII(TPMANR2)Br]+ complexes exhibited larger energy gaps between frontier molecular orbitals and >0.2 V more negative reduction potentials than [CuII(TPMA)Br]+, indicating >3 orders of magnitude higher ATRP activity. [CuI(TPMAPYR)]+ exhibited the highest reported activity for Br‐capped acrylate chain ends in DMF, and moderate activity toward C‐F bonds at room temperature. [CuI(TPMANR2)]+ could react with acrylate radicals forming organometallic species. However, this side reaction is suppressed in polymerization, because of the low equilibrium concentration of [CuI(TPMANR2)]+. Indeed, ATRP of n‐butyl acrylate using only 10‐25 part per million loadings of [CuII(TPMANR2)Br]+ exhibited excellent control.

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If you're like me, then whenever you watch a movie or video that has chess in it, you wonder if they're actually playing. In the case of Amine's latest video for "Charmander", there's a quick clip of a game. Since I've been listening to Amine some while enjoying the world chess championship this month, I have had both chess and music on my mind. Are they actually playing chess? Let's find out.

https://preview.redd.it/bos5jyep06481.jpg?width=1482&format=pjpg&auto=webp&s=e40210a9f890182abfbfc160912351202ef39aab

This is the opening position, which makes some sense. Most of the minor pieces have been developed, and the evaluation bar on the left loves white's (Amine's) position. The biggest problem with the game is that the board appears to have been set up wrong, with the black king and queen on the opposite squares they should be.

https://preview.redd.it/gb166or616481.jpg?width=1513&format=pjpg&auto=webp&s=bd3b7d2d2f0ea5b163587d9a1c03cdd85a98d6be

After black pushes the h pawn, Amine ventures out boldly with Qa4. This offers a trade of queens, and also threatens the capture of black's bishop on c4. Let's jump forward a couple of moves.

https://preview.redd.it/myk06hry16481.jpg?width=1026&format=pjpg&auto=webp&s=bd51475385e509af3a4323755a69a52456068f2d

Here, Amine moves the queen to b6 to put black's king in check. This is actually a very interesting move because if the queen is taken by the a7 pawn (which is the only legal move), black with lose both the rook and queen. Here there is a moment of realism in the video, where the girl tries to make a couple moves and Amine explains that those moves are not legal because she's in check. This leads me to believe that Amine has at least a basic grasp of the rules of chess.

https://preview.redd.it/rc4j8suf26481.jpg?width=1519&format=pjpg&auto=webp&s=cecc7634f6012fb1e5d61d4a755abbaddbf6db25

A few moves later and the game got sloppy. After RxRa8+, the black king steps forward on to the d7 square. This is an illegal move since white's bishop on f5 controls that square. Any faith that I had in Amine's chess prowess has been eliminated.

https://preview.redd.it/xr890tzv26481.jpg?width=1518&format=pjpg&auto=webp&s=c8f7605748c674f31eee51cb4fff9928cda54e0a

A few moves later, Amine triumphantly puts his rook down on d7, implying that it is checkmate. As you can tell, the black king actually has two

I've already watched the anime and read the manga of attack on titan, this was my first anime and I was really interested on it. Is there any other anime like Attack on Titan that have a great back story which makes sense, is fun to watch through and grab your attention?

Edit: Thanks guys, saved everyone's suggestions at my list :) https://imgur.com/a/F5xrasJ

So I’m a graduate medicinal chemistry student and working on anti-inflammatories. There was a purchasing error for my startin material

I got 3,4,5-trimethoxyamine instead of 3,4,5-trimethoxyaniline. So I’m stuck with trying to figure a way to convert this to this. Does anyone have a thought about how to help me? Thank you.

I have lost all the shows I have watched from this glitch basically all these random animes have went into my continue watching and I cant scroll to the bottom becuase there’s so many

Edit: thank for all the advice It still haven’t gone away but I’ll probably reinstall the app and re log into my account and see if that helps. My phone haven’t been affected so it’s probably a big and not being hacked.

Before I try Mosher's acid to derivatize it further, hopefully someone had this experience before... Please don't suggest other coupling reagents as I know they COULD work too :) It's just that I can't seem to find many reports on this.

The acyl chloride is made from phenylacetic acid and SOCl2 with one benzylic proton substituted by an alkyl group. Thanks!

Edit: This prompted me to do a SciFinder search and it seems that most phenyl alkyl ketenes can be formed using acid chloride w/ TEA or Hunig's base from 0C to RT in a few hours with fairly good yield... now it really becomes a kinetic question I guess.

I've read that via reductive amination and eschweiler-clark you can alkylate an amine OR ammonia directly by reacting it with with an aldehyde or a ketone to produce an imine that can be reduced to an amine, and this will result in a primary amine, and not a mixture of primary/secondary/tertiary amines. For example here and here both claim you can do this to ammonia directly.

For example, say I would like to make n-methylisopropylamine. First I could react acetone with ammonia and reduce the imine to pure isopropylamine, not a mixture. Then I can react this primary amine with formaldehyde and reduce the imine to pure n-methylisopropylamine, not a mixture.

However, if you google "react ammonia and acetone" some people say that this will give some complicated pyrimidine compound. Other people say it will give hexamine. Others say it results in the expected imine.

I ran into some interesting threads on sciencemadness about this. However 90% of the threads are people just making personal attacks on each other, screaming that it will result in hexamine, or that it will result in the pyrimidine, or that it will result in the imine, or that it will result in a mixture of primary/secondary/tertiary you cannot control easily. I did see one or two people who said that the result depends on ph, temperature, time, and molar excess but didn't elaborate too much.

I have a few questions. The first is, why is there any debate over this? Ammonia and acetone are very common chemcials. Has no one really reacted them together in different conditions and published the results? I would assume that of course this has already been done. But if it has, why doesn't any website I go to bother to include all the various factors and possible results?

The second question, does anyone here have experience with or know how to produce an amine from ammonia and a ketone/aldehyde? What specific factors like ph, temp, time, and molar excess are needed to result in the imine? What factors will instead result in hexamine? What factors will instead result in the pyrimidine?

The third question, the sources that claim you can make the imine from ammonia say that it will always result in the primary amine and that there will be no weird secondary reactions where the imine starts reacting with the aldehyde/ketone to result in a mixtu

Here are my top Amine songs in no particular order

• Woodlawn
• Reel It In
• Colors
• My Reality
• Caroline
• Dakota
• Burden
• Can't Decide
• Dididumduhduh
• Van Gogh
• Sh!t2Luz

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I would like to try and synthesis DMT from tryptamine using a methyl halide via the SN2 reaction and am worried about forming the quaternary ammonium salt. I'm looking for a good way to stop the reaction at the tertiary amine. I have a few ways I've theorised this could be done.

Theory 1, it does just works:

      I've heard that the tertiary amine is less reactive in SN2 than the secondary amine so maybe the reaction will naturally stop at the tertiary amine if stoichiometric quantities of the reagents are used. 

Theory 2, pH manipulation:

        The SN2 reaction makes acid as the byproduct and it needs the loan pair on the nitrogen to occur. In acidic environment the loan pair on the nitrogen will be used to bond to hydrogen so maybe with careful pH manipulation I could get the reaction to turn acidic as the tertiary amine is produced protonating the nitrogen and stopping the reaction from going further. 

Theory 3, it doesn't work and the product has to be purified later:

        I could use a slight excess of the methyl halide to ensure that all the tryptamine goes to either DMT or trimethyltryptamminium halide (the quaternary ammonium salt) and use acid base extraction to purify the DMT. This would be taking advantage of how the freebase is soluble in non polar solvents and how trimethyltryptamminium halide can't form a freebase easily. 

Let me know if any of these could work, all feedback is appreciated. And thanks for reading all this:)

What was the first Amine song you ever heard?

Located in Virginia, prices include shipping!

Amine - Limbo [Green webstore exclusive] (VG+/VG+, played once) ~ $45

Guns N' Roses - Appetite for Destruction (VG+/VG+) ~ $20

Pearl Jam - Unplugged (VG+/VG+, played once) ~SOLD

Pearl Jam - Vs. (VG+/VG+, played twice) ~ SOLD

Poncier [Green version] (M/M, still sealed) ~ SOLD

Soundgarden - Telephantasm [No Black Rain 7"] (VG/VG) ~ $65

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Thought y'all would be interested in checking it out. Decent little album overall it's only like 28 min

Got an unknown molecule mass spectra and I'm not sure where a theoretical acyl group is located. Is it more likely that it got added to the Ph-OH, or to the C-NH-C?

Evolution of activity : A facile and high‐yield synthesis of para ‐substituted tris(2‐pyridylmethyl)amine‐based ligands is presented. Copper complexes with these ligands exhibit very high activity in atom transfer radical polymerization.

Abstract

A facile and efficient two‐step synthesis of p ‐substituted tris(2‐pyridylmethyl)amine (TPMA) ligands to form Cu complexes with the highest activity to date in atom transfer radical polymerization (ATRP) is presented. In the divergent synthesis, p ‐Cl substituents in tris(4‐chloro‐2‐pyridylmethyl)amine (TPMA3Cl) were replaced in one step and high yield by electron‐donating cyclic amines (pyrrolidine (TPMAPYR), piperidine (TPMAPIP), and morpholine (TPMAMOR)) by nucleophilic aromatic substitution. The [CuII(TPMANR2)Br]+ complexes exhibited larger energy gaps between frontier molecular orbitals and >0.2 V more negative reduction potentials than [CuII(TPMA)Br]+, indicating >3 orders of magnitude higher ATRP activity. [CuI(TPMAPYR)]+ exhibited the highest reported activity for Br‐capped acrylate chain ends in DMF, and moderate activity toward C−F bonds at room temperature. ATRP of n ‐butyl acrylate using only 10–25 part per million loadings of [CuII(TPMANR2)Br]+ exhibited excellent control.

https://ift.tt/2X7StCM