Organic Chemistry

[“it’s unheard of!” –Milton Estelle, biology teacher]

the plants in this room
at this moment are dazzling- sparking
up the staged magnesium so
the act commences, Kafka’s high-
wire sorrow, but it doesn’t matter,
doesn’t matter, there’s a secret-

it’s the organic sugar miracle-

outside of man’s domain, this is
-six ©ohtwo plus twelve(h)two(oh) arrow-

all the chemical pathways-
the dropped electrons swinging
over lakes over blue houseplants
that are the cats of the universe, still
and silent and all unknown-

this is what man cannot do-

except at the game before the lights turn on
the inorganic air sparkling-
the unheard of speculation-
then there is this

cellular sugar
while high-
fly backfield, coach in his orange shirt
loud, houseplant cats perched over the
announcer box and transfiguring the amplified
VOICES something-

outside of understanding, this is
-c(six)h(twelve)oh(six) plus (SIX)oh(TWO) plus


no magic-
just light, and water

—  L. Maruska

Nickel(II)-sulfate hepta/hexahydrate crystals what were grown in the lab during the winter break. They are not perfect, but they look pretty.

It’s interesting that while anhydrous nickel(II)-sulfate is a yellow solid, the hexahydrate (6 molecules of H2O for each NiSO4) is blue and the heptahydrate (7 molecules of H2O for each NiSO4) is greenish-blue. As seen on the picture these are probably heptahydrates, but they will dehydrate by standing on air to give the hexahydrate.

Nickel sulfate occurs as the rare mineral retgersite, which is a hexahydrate.


Cool Chemistry: How Many Nitrogens Are There?!

Explosives chemistry (often referred to as the more innocuous-sounding “energetic materials”) is a highly active area of research. One of the leaders in the field of energetic materials is Dr. Thomas M. Klapötke (Ludwig Maximilian University of Munich, LMU). Klapötke’s specialty is synthesizing molecules containing large numbers of nitrogens: one of of his most notorious synthetic targets is shown above, with no hydrogens, only 2 carbons, and a jaw-dropping 14 nitrogens! This molecule was, somehow miraculously, characterized by X-ray crystallography, IR and Raman spectroscopy, and 13C and 14N NMR spectroscopy (not shown); detonation sensitivity tests were also performed, as well as a computational study to calculate the charge distribution in the molecule.

So what gives high-nitrogen compounds their explosive habits? The fundamental reason is that formation of nitrogen gas, N2, is highly favorable. The N-N triple bond of dinitrogen is one of the strongest bonds known in chemistry with a bond dissociation energy of 226 kcal/mol, making N2 an extremely stable molecule. (As a comparison, the dissociation energy of a typical C-C single bond is roughly 85 kcal/mol.) Any nitrogen that is produced also readily escapes from the system since it is a gas, increasing the entropy of the overall system.

The higher the mass fraction of nitrogen in a molecule, the more unstable it tends to be, especially when those nitrogens are bonded together. In the case of C2N14, the molecule is on the brink of not existing at all–the bulk compound will detonate at impacts less than 0.25 J or friction forces smaller than 1 N, which both deliver miniscule amounts of energy. In fact, detonation even occurred while taking an IR spectrum! (How they were able to get a crystal structure without destroying their X-ray diffractometer is beyond me.)

Although C2N14 is far too explosive to have any practical use in everyday life, further energetic materials research could potentially use the knowledge gained from these highly unstable compounds to create explosives more powerful than the current ones available that can be easily handled and controlled.

Reference: Klapötke, T. M.; Martin, F. A.; Stierstorfer, J. Angew. Chem. Int. Ed. 2011, 50, 4227-4229.
Lecture List for University Chemistry Courses

Chemistry Courses Included:

  • General Chemistry
  • Organic Chemistry
  • Biochemistry
  • Analytical Chemistry
  • Physical Chemistry
  • Quantum Chemistry
  • Inorganic Chemistry
  • Computational Chemistry
  • Medicinal/Pharmaceutical Chemistry
  • Polymer Chemistry
  • Chemistry Lab Technique
  • Chemical Engineering
  • Biotechnology
  • Metallurgy

This is an amazing resource for anyone currently studying these courses, studying these courses in the future, or anyone interested in the subject. Enjoy and please reblog so more people are aware!

A large crystal of potassium ferrocyanide. 

Potassium ferrocyanide is the inorganic compound with formula K4[Fe(CN)6] * 3H2O. At us it is called yellow blood salt, what comes from it’s historical production. Long ago it was manufactured from organically derived nitrogenous carbon sources, iron filings, and potassium carbonate. Common nitrogen and carbon sources were torrified horn, leather scrap, offal, or dried blood.

A famous reaction with this compound involves treatment with ferric salts to give Prussian blue [Fe4[Fe(CN)6]3].


Years ago, a large amount of H(CuBr2) was made by adding copper(I)-bromide to a concentrated hydrobromic acid solution in acetic acid. This reagent is used in Sandmeyer reaction, for replacing a diazo group to bromine on an aromatic ring.

The interesting thing in these crystals, that they are highly hygroscopic, deliquescent, so I had to photograph them in a closed glass tank. And the crystals are like a rubber, they could be easily squeezed, they wont break, just bend. 


you’re so radical

frémy’s salt is also formally known as potassium nitrosodisulfonate. in the salt’s crystal lattice, the radical potassium nitrosodisulfonate exists in dimeric form. depending on the bonds between the oxygen atoms (covalent or non-covalent), the crystals either appear bright orange to yellow and exhibit diamagnetism or are dark orange to brown and paramagnetic.
This specimen of frémy’s salt was produced by dissolving sodium nitrite and potassium metabisulfite in ice water and adding glacial acetic acid and ammonia. potassium permanganate was added as an oxidising agent to produce nitrosodifulfonate ions and manganese(iv) oxide, which was removed through filtration. the purple filtrate was kept in ice water to accelerate precipitation of the salt, which was then dried over potassium hydroxide.

potassium nitrosodifultonate is, due to its radical character, prone to spontaneous decomposition if exposed to air. so be extra-careful or watch out for small explosions!