Anyone have a favorite coupling reagent for selectively reacting with an amine vs. an alcohol? The amine is primary so it should be favored over the secondary alcohol, but unpublished results from the original synthetic work by someone else looks like you get a mixture of amide and amide/ester (not sure if no ester alone is formed or if they removed it upon purification, I don't have all of the details).

I don't particularly want to swamp the reaction with a large excess of the amino-alcohol because I will probably have to recover it, however the acid is precious enough (many more steps to make) I'll do that if necessary.

#Chemistry #ChemiVerse

Run two reactions on related substrates in parallel. Ran the column for the first on Friday, everything looked good, so set-up step 2 over the weekend.

Ran the column on the second reaction this morning. No peaks. The TLC had spots! The reactions were the same scale! tears hair out

(at least it looked like step 2 on the first reaction worked, but that wasn't really in doubt since I've done it before, step 1 was a different protocol)

#LabLife #Chemistry #ChemiVerse

Published today!

Lee, Grace Juwon, and Rebecca M. Jones. 2026. “Shielding through Time: Bridging the History and Teaching of Slater’s Rules.” Journal of Chemical Education

https://doi.org/10.1021/acs.jchemed.5c01117

#ProfLife #Chemistry #Chemiverse

Very nice collection of (organic) chemistry links and resources from @acsorganic

Pretty amazed that they have an advisory board for this resource, and it seems (at first glance) to be pretty up-to-date.

Kudos!

https://www.organicchemistrydata.org

#Chemistry #Chemiverse

Me: "For its age this pump looks remarkably clean"

Drains oil, puts in a small amount of fresh oil, runs for 30-45 min, drains again and there is a lot of particulate.

Me: "Hmm"

Opens pump to find out the reason it was clean on the outside was probably because people weren't changing the oil frequently enough.

#LabLife #LabNightmares #Chemistry #ChemiVerse

"How Bell Labs Won Its First Nobel Prize” by Brian Potter.

A great read about the 1925 Davisson and Germer experiment (the canonical “electrons have wave properties” xpt that our chemistry undergrads learn about in physical chemistry class).

Such a long and winding road from inception to realization of what they had discovered. I was unaware of all the details, and found this very enlightening!

#Chemiverse #Chemistry #HistoryOfChemistry

https://www.construction-physics.com/p/how-bell-labs-won-its-first-nobel