Squaric acid is an unusually strong acid for an organic acid:
It's also unique because of its strained ring. In general, five- and six-membered rings dominate in chemistry - hence the endless parade of hexagons. Higher rings are tolerated but not-so-favored. Lower rings are possible, but, again, unfavored, because one tends to find atoms' electrons in clouds that don't overlap so well in this configuration. Along with some other moderately strong organic acids (such as the ubiquitous "alpha-hydroxy acids"), it's attracted some attention for (prescription) dermatological use.
- Log in to post comments
More like this
As we head into the Science Spring Showdown Sweet Sixteen, it seemed prudent to turn to some experts for their predictions on the two remaining games in the chemistry region, Acid vs. d-orbitals and Fossil fuels vs. Erlenmeyer flask. (Of course, we won't soon forget the exciting first and second…
"In three words I can sum up everything I've learned about life: it goes on." -Robert Frost
Well, here we are, at the end of the week, and you know what that means: another Ask Ethan column! This week, I've been asked about the same thing by many different people, so I'll credit it to Patrick E.…
Lots of us knew melamine as a heat resistant plastic polymer found in kitchen items, like plastic plates. Despite its reputation for heat resistance it would melt in an oven, although it doesn't catch fire. It is used in a lot of other places: floor tiles, white boards, fabrics, filters, even the…
Last week's post talked about the general idea of negative temperature, with reference to this much-talked-about Science paper (which also comes in a free arxiv version from which the figures used here are taken). I didn't go into the details of how they made a negative temperature gas, though, and…
Oh boy oh boy oh boy! Acetylene dicarboxylic acid diperoxyesters, -OO-t-Bu, -OO-CF3, -OO-SiMe3, your choice. Frozen matrix then photolyze to get .C#C. (acetylene diradical) insulated by a CO2 on either end. Wouldn't that be the Big O for spectroscopists and organic theory scum? (C2 Swan band emissions in comet tails, (0,1)/563.5 nm, (0,0)/516.5 nm, (1,0)/473.7 nm, (2,0)/438.2 nm.) It's got to rehybridize when cold, but to what? Degeneracy = publishable.
Warm the matrix to get radical recombination and RO-C#C-OR. Acetylene diethers are trippy. But wait! Iodine trap half, get a [(pi)2a+(pi)2a] for the unsaturated four-membered ring (we are sooo naughty!). Hydrolyze, get squaric acid.
If you hurry the RFP and PO you can bootleg it over X-mas to New Years. Admittedly that first step is potentially explosive and acetylenedicarboxylates require some art to be made. Nasty for skin contact, too. Could it be more fun?