[kbomar]

Hello,

I am working on a personal project. I am trying to examine the effect of an electric field on Diels Alder Reactions. I am utilizing a molecular dynamics software to do this initially but hope to move to the lab if the simulation output looks promising.

I am looking for a diels alder reaction that is fast and reversible at room temperature. Does anyone know of any? I know these are not typically qualities possessed by this mechanism, but I have found a couple examples that get close.

If you are not sure any that have been study, could you postulate what types of R groups, or other molecular properties of the diene and dienophile pair might facilitate these qualities?

Thanks for any and all help, it is much appreciated. Cheers!

[AWK]

Search literature.
Even Dr. Google has a lot of suggestions for you. Hint: Diels Alder reaction at room temperature.

[kbomar]

Hi AWK, thanks for the reply. Dr. Google and I are acquainted and I am certainly searching the literature. My searches were a little too specific, perhaps. To clarify though, when I said room temperature reversible I meant that I am look for a set of reactants that not only undergo a diels alder reaction at RT but that their product also undergoes a retro diels alder reaction at RT. Essentially I am looking for a diels alder equilibrium with a reaction constant in the range of 1000 to 0.001 at RT and I need it to be relatively fast.

Through my search I have yet to find one discussing a room temperature reversible reaction that is also fast as I have stipulated. I pose this question not as my only method of information generation, but as an augmentation. I am asking on the off chance anyone here has had experience with a reaction like this directly. I don't want to offend anyone by coming off as not having done some background search myself.

[wildfyr]

Furan and maleimide go at RT and reverse diels alder at a reasonable higher temp like 100C.

[kbomar]

Wildfyr, thank you for the information! I am looking further into that reaction now. Maybe there is a slightly substituted version of this pair that would hit the sweet spot, this pair is certainly close.

[wildfyr]

I'm proud enough of this one to accept a paper acknowledgement or something

[kbomar]

Would you like the nobel prize sent to your home or office?   

[wildfyr]

Office, my coworkers should see it

[Corribus]

Plus that way he can put it next to the others.

[phth]

I would read into activation volumes etc. Interesting stuff in regards to transition state theory. See high pressure DA reactions...

https://pubs.rsc.org/en/content/articlehtml/1970/tf/tf9706602579?casa_token=W6DWTKiyxB8AAAAA:uJEZas_f7L1VAOEm8PHFiG80lTrKUyFNtCMgNISLrjYldSEuK3Id8NynqVXa5H6ZwnNMUlBpug_uIa0[/url]

Hello,

I am working on a personal project. I am trying to examine the effect of an electric field on Diels Alder Reactions. I am utilizing a molecular dynamics software to do this initially but hope to move to the lab if the simulation output looks promising.

I am looking for a diels alder reaction that is fast and reversible at room temperature. Does anyone know of any? I know these are not typically qualities possessed by this mechanism, but I have found a couple examples that get close.

If you are not sure any that have been study, could you postulate what types of R groups, or other molecular properties of the diene and dienophile pair might facilitate these qualities?

Thanks for any and all help, it is much appreciated. Cheers!

[Enthalpy]

Cyclopentadiene. Direct at RT, reverse needs heat.