backside attack

the touch, the feel of carbon the atom of our lives aka carbon bonded to things* *not necessarily due to attack of its backside, in case you are a mechanistic purist

[compoundchem]

Love coffee? Here are the chemical compounds that make that morning coffee smell so good. Larger image: http://wp.me/p4aPLT-YM

[labphoto]

My new favorite, the Eschweiler–Clarke reaction!

The Eschweiler–Clarke reaction (also called the Eschweiler–Clarke methylation) is a chemical reaction whereby a primary (or secondary) amine is methylated using excess formic acid and formaldehyde. Reductive amination reactions such as this one will not produce quaternary ammonium salts, but instead will stop at the tertiary amine stage. It is named for the German chemist Wilhelm Eschweiler (1860–1936) and the British chemist Hans Thacher Clarke (1887-1972).

The mechanism of the reaction is really simple, first methylation of the amine begins with imine formation with formaldehyde. The formic acid acts as a source of hydride and reduces the imine to a secondary amine. The driving force is the formation of the gas carbon dioxide. Formation of the tertiary amine is similar, but slower due to the difficulties in iminium ion formation.

The only problem was, that the yields were at a maximum 60%, but for the first run it’s not that bad.

[columbiascience]

Columbia researchers recently published work using quantum mechanics and a supercomputer to reveal how the world’s strongest, thinnest materials break. The study was inspired by previous work on graphene and found that several other monolayer materials have a very similar failure mechanism despite having extremely different electronic properties.

Their results contradict previous explanations of why graphene breaks based on a well-known concept in physics called a “Peierls instability”.

Image: Top and side orthographic projections of the distorted structures for (a) graphene, (b) BN, (c) graphane, and (d) MoS2 at equibiaxial strains of 0.212, 0.240, 0.328, and 0.270, respectively. The C, B, N, H, Mo, and S atoms are represented as brown, green, silver, white, purple, and yellow spheres, respectively. Dashed lines indicate the undistorted strained lattice.

[sigmaaldrichofficial-deactivate]

Let’s talk about one of my favorite reactions: the benzoin condensation! This reaction is formally a disproportionation reaction: the carbonyl carbon goes from a +1 state in the starting material to 0 and +2 in the hydroxyl and new carbonyl carbon, respectively.

At first glance, this reaction appears to happen by simple nucleophilic addition to one of the carbonyls. However, this is not the case at all; benzaldehyde is not readily deprotonated, with a pKa close to 15. In fact, because of the carbon-oxygen double bond, that carbon is highly electrophilic! How does this reaction proceed? The answer lies in the cyanide catalyst. Let’s examine the mechanism more closely to figure out what exactly goes on…

Read More

[organicchemistrylab]

Everyone knows oil doesn’t mix with water. In chemistry we also use this to purify our compounds! The top layer is oily/non-polar (ethyl acetate) while the bottom is water/DMSO. My product should be oily so it should go in the top layer!

[ilgeffo]

Ever been in that position where you can’t decide between a flask and a beaker?  Worry no more; Fleaker is here!

[labphoto]

The brominated Wilkinson catalyst: RhBr(PPh3)3.

It has a beautiful color(:

[ap0stasis]

The glass caffeine molecule came today! It’s really pretty, intended as a gift to my great chemistry treacher.

[postcard-from1952-deactivated20]

literally the only reason i can memorize the TCA cycle

woo, biochemistry!

[backsideattack]

carbonic anhydrase

[labphoto]

This pretty yellowish stuff is some highly toxic and hazardous organomercuric reagent what was made in situ from some mercury(II)-acetate and an alkene.

Real, sweet organometallic chemistry(:

[wetwareontologies]

[molecularlifesciences]

DNA codons to Amino Acids!

Really cool visual, but may be a little to busy for learners.

[backsideattack]

via Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

[libertasacademica-deactivated20]

Figure 4 from ‘Drug Target Exploitable Structural Features of Adenylyl Cyclase Activity in Schistosoma mansoni’ Published in Drug Target Insights

[labphoto]

Left side: my starting material, a highly substitued pyrrole (also prepared by me), right side: the compound what I have made from it. They look awesome under UV(:

[labphoto]

Some crystals formed at the bottom of the breaker. They could be potassium bromide… Or maybe some benzyl-amine-hydrobromide… Who knows?

[backsideattack]

Structure of the Adenosine A2AReceptor in Complex with ZM241385 and the Xanthines XAC and Caffeine

in honor of all the upcoming caffeine binges/orgo cramming the new semester will bring. good luck, everyone!