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MurphysLab OP t1_jbifznn wrote

/u/BiochemistChef's response is great, so I'll try not to repeat.

Instead, I'll highlight another aspect: A ring containing 6 nitrogen atoms and 6 electrons in pi-orbitals is something which theory has predicted could exist for a long time and which we might make. But while theory is good, reality is always more interesting. Reality often functions as the measuring stick by which we can see if our theories are correct or not. That's the fundamental nature of science.

Consider those physicists who keep on proving Einstein right again and again: They're checking to see if reality looks the same as our theoretical understanding.

Another aspect of why this was published in a prominent chemistry journal (and why I'm rather enthused about the result) is that benzene has very interesting chemistry which is the result of the special arrangement of electrons which it possesses. It's the foundation of huge swaths of chemistry. And so chemists have seen how we might modify it so it's not just 6 carbon atoms in a ring.

Chemists wonder "What happens if we start swapping out some of the 6 carbon atoms in a benzene ring for different atoms?" Those molecules are termed heterocyclic compounds.

https://i0.wp.com/www.compoundchem.com/wp-content/uploads/2014/07/Heterocycles-graphic.png?ssl=1

What happens if you swap 1 carbon atom with a nitrogen atom? Pyridine is just that and it's a motif which appears frequently. The nitrogen allows chemists to use it as a ligand for metal atoms.

What if we replace 2 carbon atoms with nitrogen atoms? We've done that. It give you pyrimidine, pyrazine, and pyridazine, each with different chemical properties.

You'll note that the series doesn't stop with just 1 or 2 nitrogen atoms substituted. We can imagine a complete series:

  • 6-membered rings with zero nitrogen atoms: benzine
  • 6-membered rings with one nitrogen atom: pyridine
  • 6-membered rings with two nitrogen atoms: diazines
  • 6-membered rings with three nitrogen atoms: triazines
  • 6-membered rings with four nitrogen atoms: tetrazines
  • 6-membered rings with five nitrogen atoms: pentazine (still only hypothetical)
  • 6-membered rings with six nitrogen atoms: hexazine

Using series of molecules like that, we can better understand why they have the properties that we observe and how we might plan to change the properties of other similar heterocyclic molecules.

I'd add that many of those N-heterocycle motifs turn up in really useful molecules. For a munch of my PhD, I worked with plastics containing polyvinylpyridine to make cool nano patterns.

Those nitrogen containing aromatic molecules also turn up in pharmaceuticals:

Many of those need the nitrogen(s) in the ring for efficacy, so it's also worth exploring new synthetic methods for making nitrogen heterocycles. They aren't typically using lasers and diamond anvil cells, but the future might hold some surprises.

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sojayn t1_jblqn40 wrote

Thank you so very much for this. Beyond the pure beauty of it, the “what happens?”, I had no idea about the medical application and now can reverse engineer my knowledge of that field a little.

Fascinating to see the intersection, and I am grateful for you all for taking the time to show me.

Stay safe all of you, just watched the fairly inaccurate Radioactive movie about M Curie and don’t want any of you sleeping with glowing heterocyclic vials on your pillows!

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