The Tale of Jamesonia

Hello from Jamesonia! If you haven’t heard of this kingdom before, no worries! (Though actually, I have to say you could do a little with some geography). Anyway, I’ll give you some insights about Jamesonia- our geography, weather and climate, culture, major professions, everything. Just stay with me.

First things first, Jamesonia is located on the north side of the third floor of Science Center. It is a small kingdom with an approximate area of 800 sq. feet. There are two current citizens of Jamesonia- Professor Donald Jameson, and me. Oh, by the way, I am the chief assistant to the professor and the only employee of the Department of Everything in Jamesonia. Did I forget to say my name? I am Meem. I am a rising senior majoring in Chemistry and minoring in Writing.

Back to Jamesonia. In terms of weather, we are a kingdom of forever winter. In the middle of hot summer, you’ll probably still see me shivering in my pink sweater if you pass by our kingdom. Our winter is not very different from the rest of the kingdoms in the continent of Science Center. (If anyone says our kingdoms are labs and Science Center is a building, not a continent, just ignore them).

So, let me tell you a little bit more about life in Jamesonia. Who knows, maybe you’d love our culture and want to visit! (We love tourists!)

See, I told you we love North Carolina!

In terms of laws, our first and foremost law is to never speak ill of North Carolina. We love North Carolina here. If you look at a pretty happy clear sky in the summer and a citizen of Jamesonia asks you what color the sky is, the ONLY correct answer is CAROLINA BLUE. So, when we finally have our own Jamesonia flag, it is definitely going to be Carolina blue.

Secondly, all citizens of Jamesonia go on a weekly coffee chat where they bond over agreements and disagreements, and endless debates and discussions on very important things in life, such as, if having a goat is more efficient than having a lawn mower.

Now, let’s talk work. We basically make new molecules here and determine their structures and see how they behave. So, we make cobaloxime complexes of camphorquinone dioxime and study their properties. Wooh! That was a mouthful! No worries, you don’t need to remember all that. That was just the official terms I have to write in documents (and theses!!). But since this is not an official document (royal document of the Kingdom of Jamesonia), I can break those terms down into simple words for you.

Cobaloximes are cobalt coordination complexes modeled after vitamin B12.This means these are molecules with a Cobalt in the center, and a bunch of other stuff that the Cobalt has made friends with and is holding onto. Together, they are mimicking the structure (and many of the properties) of vitamin B12. (Think about when you tried to mimic that favorite actor of yours, except, these molecules are a little bit more skilled at mimicking). We hope these complexes have potential uses in catalyzing the conversion of solar energy to hydrogen gas, and new photochemical reactions.

Here’s a picture to help you understand how camphorquinone dioximes are prepared. As you can see, it has four different isomers!

In Jamesonia, we make cobaloxime complexes using camphorquinone dioximes. Now, what are they? They are a derivative of camphor. Well, I wish we had developed the technology to upload smell with photos (Jamesonia might consider trying that, in some future). If I could send you the smell of camphor, you’d instantly recognize it. Yes, camphor is a compound you probably know. It is used in medicines such as antiseptic, anti-inflammatory, and nasal decongestants. You take two nitrogens, each having an oxygen friend and a hydrogen tagging along, and you stick them to a camphor. Boom! You have camphorquinone dioxime!

We are very good peace ambassadors and communication officers here. We help camphorquinone dioximes become friends with a Cobalt. The goal is for them to stay together, forever. Since our Cobalt has six hands that it wants to hold friends with, and it only needs four hands to hold two camphorquinone dioximes, we give the molecule two other friends to hold onto, as well.

This summer, I have successfully added two 4-picoline molecules in the friend group to make a novel cobaloxime complex of camphorquinone dioxime. Due to the nature of camphorquinone dioximes, we ended up having two different isomers of the molecule I prepared, but I was able to separate the two isomers. When I say isomers, think twin siblings, with all same physical traits but slight differences. But see, I understand they are twins and everything, but they are grown up now and need to go in their own ways. (No! I’m not a villain! I’m only saying they are grown up now and need to go in their own paths to fulfill their own dreams. One of them wants to be an astronaut and the other one wants to be a painter). But oh boy, they were really not willing to part ways. So we had to kinda trick them by putting them in a race, and then capturing them separately at the end of the race.

This is the reaction I did to add the two 4-picoline (a pyridine derivative) friends to cobalt’s friend group. You can see the two isomer siblings here.

Oh, yes, speaking of that- by this time, some of you might have started wondering about how it is like to be a citizen of Jamesonia or maybe even considering applying to be a citizen. I’ll give you a little warning. In Jamesonia, we run a lot of column chromatography. In fact, that’s how I separated the two isomer siblings. In column chromatography, we take a long glass tube stuffed with some cotton and a lot of silica gel or alumina and pour a solution of the compound we want to separate, along with a mixture of solvents. The solution goes down through the silica gel (or alumina) and the isomers get separated in the process. The less polar isomer is generally better at racing, and so it comes down first. We collect it and separate it, and then the slow racer (more polar isomer) comes down and we collect it separately.

Here’s a column I am running

Now, I know you are wondering what any of these have anything to do with your citizenship. Well, if you are not a very tall person, you might be at a disadvantage. See, I am not super tall, and my legs have been tired of tiptoeing to help my hands in pouring solvents on long columns. (Or you can be smarter than me and just use a stool!)

Anyways, let’s get back to the story of cobalt and its friends. I have been able to help cobalt make some new friends. After making the friend group of cobalt with camphorquinone dioxime and 4-picoline (a pyridine with a methyl friend), I proceeded to help cobalt make some other friend groups. This time, I had to be a little bit of a villain I guess. Emma Armstrong, a former citizen of Jamesonia (Class of ’22), made a complex where cobalt had two camphorquinone dioxime and two bromine friends. However, the bromine was tired of being just with one friend group for so long and wanted to go exploring for more friends. So we had to free the bromine, for which, we had to give cobalt two new friends to replace the bromines. Now, you can’t be cruel to someone and take two of their friends away at once! So first, we only replaced one bromine with a triphenylphosphine group. Cobalt was a little upset, but we ran the new friend group through column chromatography, and at the end, they became good friends, and cobalt was okay with a bromine leaving. Once cobalt got used to not having a bromine, it was time for us to help the other bromine be on its way. This time, we were going to replace the bromine with a methyl group. This time, cobalt was really upset. We tried running the friend group through a column, but even that didn’t work. Cobalt was so upset that it refused to even race. The compound stayed on top of the silica gel, and wouldn’t race, no matter how much we tried to lure the friend group with a solution of dichloromethane and methyl-tert-butyl-ether (MTBE), two solvents who work as staff in the race. So, we were unable to make that friend group. In official words, our reaction didn’t work.  

Given that our cobalt is a very sociable element who wants to have friends around all the time, and that cobalt and camphorquinone dioxime have been friends in our kingdom for a long time, we decided to give cobalt a new friend group, this time letting camphorquinone dioxime explore some other possibilities in life. So we decided to give cobalt a friend group that is close enough in appearance to camphorquinone dioxime, but it’s not the same molecule. We used another derivative of camphor, with an oxygen friend holding two hands, and a carbonyl group friend holding one hand. We made a ligand (bigger friend group with more hands to hold onto cobalt) by introducing this molecule to a new friend- ethylenediamine. They became friends very happily and formed the ligand. It was a white powder. However, this new friend group did something interesting. They formed isomer siblings, except, this time, one isomer did not want to be here. It was trying to go in its own way, probably tired of its sibling (as most people are). When we filtered the final solution with methanol after our reaction, we got just one isomer. The other isomer dissolved in methanol and stayed in the filtrate. But, there was an eensy teensy issue. Just because one isomer was tired of its sibling, doesn’t mean the other one was too! In fact, it wanted to be with its sibling to have the chance to annoy the sibling even more. So in the filtrate where there was only supposed to be one isomer, we kept finding some of this “right” isomer there every time we filtered the filtrate. We lovingly call this compound (fcamph)2en.

The top reaction is how we made the (fcamph)2en compound. The bottom reaction shows what we tried to make cobalt become friends with the new ligand.

How was that happening? We came to the conclusion that while the “wrong” isomer sibling decided to slip away by dissolving in methanol, it didn’t know that its sibling, the “right” isomer partially had the ability to slip away in methanol. So some of the right isomer kept following the wrong isomer into methanol, and we had to filter many times to get, in official language, a good yield. When we reached a yield of 40%, which means, 40% of our old friend groups had converted to this new friend group, we called it good enough.

The isolated right isomer

(Hey, listen. I’ll tell you a secret. But, shhh… Don’t tell the right isomer, we are trying to develop a more efficient method to synthesize just the right isomer. In simple words, we are trying to come up with a way to trap all the right isomer in the filter to get a better yield.)

Next, we introduced this friend group to cobalt to see if cobalt would accept a new friend group. Unfortunately, cobalt tricked us in a very smart way this time. We use a technique called NMR (Nuclear Magnetic Resonance) that allows us to see how many hydrogens and carbons are in a friend group, and where they are in the friend group. In our NMR spectroscopy, we kept seeing two extra doublet peaks (meaning, there are more hydrogen friends than there should be, imposter alert!) no matter what we did. So far, we have tried several methods of purification to find and separate the imposter, but the imposter is apparently very good at hiding. Oh well, we will get it very soon. We are on it.

Here are some cobalt friend group complexes we made this summer

Now, if you think we only make friends in Jamesonia, while I’d like for that to be true, we actually do more than that. We do a lot of adventure here. For one, Professor Jameson and I are currently in an adventure of doing cyclic voltammetry (CV), something neither of us have done before! This is a technique that should be able to give us an idea about some aspects of our cobalt complexes’ (the cobalt friend groups) personality., namely- electrochemical properties. CV should tell us about the friend groups’ willingness and ability to adopt an electron or put up an electron for adoption.

If you want to know more about that, you are always welcome to visit Jamesonia to see our work in person!

Oh, did I tell you, the best part about Jamesonia is that here we believe the world is home to all of us, and so our doors are open to tourists, without any restrictions. You don’t even need a passport to visit Jamesonia, let alone a visa!

However, if you do want a citizenship of Jamesonia, we have some dress code restrictions. While in Jamesonia, you must always wear closed-toe shoes, and while working, you must always wear safety glasses or goggles. Please protect your eyes, because here, we learn to admire the beauty of the small things in this immense universe, and your eyes might help you spot and appreciate very unexpected pleasant surprises around you.

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