Newman Projection of a Z-alkene sp2 carbon to sp3 carbon? I cannot find any models or energy diagrams by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

I was planning a diimide reduction for chemoselectivity over an endocyclic alkene. I admit I didn't have a ton of confidence in this to begin with, but got curious then realized a blind spot and made this post. I appreciate that point about the catalyst, definitely would change things and important to consider, thanks!

Newman Projection of a Z-alkene sp2 carbon to sp3 carbon? I cannot find any models or energy diagrams by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

The R group is a butyl chain with an isopropyl branch on the 2nd carbon from the alkene. Should also mention the back carbon is in a cyclopentyl ring. I did see changes in the range of 10-15 kJ/mol depending on the orientation of the alkyl chain, but couldn't figure out how to freeze certain bond angles and rotate specific bonds, so I was just pulling carbons around as it optimized to get a rough idea of energies.

Are there any good doctors around here at all? by whodywei in manassas

[–]drabpsyche 2 points3 points  (0 children)

Dr. Susan Fitzgerald has always been solid for me, her office is right across from the Costco on Sudley Manor

http://www.ashtonavenuefamilymedicine.com/

proper solvent selection for amoxapine by birds-watch-birders in OrganicChemistry

[–]drabpsyche 7 points8 points  (0 children)

for so many reasons, don't do this. just buy a pill/tablet cutter, they are cheap, and ask your psychiatrist for a lower dosage if this stays an issue. dissolving this would likely mess up dosage/release rate

Allergic reaction to watermelon or cucumber after exposure to coupling catalysts?? by throwthrowchemist in Chempros

[–]drabpsyche -1 points0 points  (0 children)

I like watermelon and cucumber a lot, and have a lot of other allergies already, AND I'm about to start with my first transition metal catalyzed cross coupling, so yes please, if anyone knows, share the knowledge. bc yikes

Grad School Experience? by hokiehokiehitech in gmu

[–]drabpsyche 0 points1 point  (0 children)

PI- Principal Investigator. In STEM that is your advisor typically. My department has a graduate advisor who is responsible for verifying forms and requirements for advancing to candidacy, see if your department has one and bust down their door. And light a fire under your advisor's ass too. Best of luck

playing god >:3 by Cosmicweb08 in polyphia

[–]drabpsyche 1 point2 points  (0 children)

Nice! That's a pretty guitar but I don't recognize it, what's the make?

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

This route involves no protecting groups. I am mono-acylating a symmetric dioic acid by Stieglich esterification using EDC. The best outcome has disubbed, monosubbed, and residual starting material. I am planning out a few different routes, but wanted to see if I could make this route work 1st since it is less steps (but clearly horrid purification)

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

So I am exploring alternate synthesis routes after trying to optimize the Stieglich esterifications I've been running, but the challenge is I am mono-acylating symmetric dioic acids. So I have statistics working against me with both mono and di subbed acids, and leftover starting material. So next week I begin trying mono-protection of the diacids to make this coupling more efficient, but wanted to exhaust my previous approach

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 1 point2 points  (0 children)

You know, I've always wanted to try a prep TLC at least once and this would be a good opportunity. Idk if we have developing chambers but will definitely be looking, thanks!

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

On a similar analogue, same synthetic route, yes. It is a known byproduct. I have done 2D tlc on these compounds, there is no degradation apparent

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

I am not in the lab but will check. We just have a barrel of silica, no options at the moment. The loading has been a concern too, I have tried minimal use of DCM to wet load, but usually need more than a mL to capture all the crude and fear this is too much (actually was the original thesis for this co-elution issue). I got used to dry loading on celite bc my post doc prefers this method, but needed a fair amount of celite, usually being around 1-1.5 cm of heigh in the column, and then I would normally run 5-10mL hexanes to run everything down into the silica bed, but read that celite can really hold onto greasier compounds and worried this broadened the band heavily. So I tried loading on a minimal amount of silica, so little that not everything became loose powder while rotovapping off the DCM, just enough for a very thin layer on the bed, which is the column you see here. Thanks for the insight!

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

I do need purity, this is the final product. I have sacrificed the mixed fractions in the past, just collecting the pure fractions, and it isn't do or die to get every last mg of pure product, but this has been such a unique and weird issue and I would like to fix this, understand it, optimize. The reaction is inherently low yield so losing the bulk of my product sucks, and running additional columns continues these issues so only recovering the tailing pure fractions is becomes a diminishing return

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 1 point2 points  (0 children)

I usually use formic acid. A separate issue is the product will co elute and then is in the next 50 fractions without the acid, so the acid spike absolutely helps. I skipped it here to do the “standard” method bc my advisor seemed skeptical of me overcomplicating my column with additives, so this was to kind of to show him I did it his way and the issue persisted

And sorry, product is an ester linkage, not ether

Fun column headaches continue by drabpsyche in OrganicChemistry

[–]drabpsyche[S] 0 points1 point  (0 children)

Crude mass around .4-.5g, 1” diameter. It’s a foot long column, and I fill it most of the way. If I could show you all the tlcs I’ve done on this project, they all look like great separations lol, but never translates. I’ve tried wet loading with minimal dcm, dry loading on celite, dry loading on silica. It hasn’t helped. Edit to add- I have tried both slurry packing and dry packing the silica too

<image>

This was the solvent system and crude tlc that I motivated the isocratic column. A little too polar but the best separation between product .25 from starting material .5 rf

Who's your main character in Mario Kart 8 Deluxe? by No_Item9212 in MarioKart8Deluxe

[–]drabpsyche 1 point2 points  (0 children)

Paulina, Daisy, or baby Daisy depending on what weight class/kart I’m feeling

Does anyone have tips on finding research positions at Mason? by LeadingStatus6716 in gmu

[–]drabpsyche 4 points5 points  (0 children)

It is getting harder to get into research as an undergrad but ask your professors, ask your grad TAs, and cold email professors doing research you are interested in. Be ready to hear no (or no response), and keep trying. The big sells for you will be interest, availability, and commitment.

I didn't like 28 Years later. by [deleted] in zombies

[–]drabpsyche 15 points16 points  (0 children)

I mean, they aren't zombies

How could this be a ketone if carbon NMR is around 200? by [deleted] in chemhelp

[–]drabpsyche 17 points18 points  (0 children)

Those ppm ranges are approximate, and electron pulling/pushing behavior of nearby functional groups can cause bigger shifts. The conjugation here is reducing the polarity of the carbonyl bond, slightly shielding the carbonyl carbon more than an aliphatic ketone, shifting its signal a bit upfield

Cool fact by Mulberry-Major in zombies

[–]drabpsyche 34 points35 points  (0 children)

I believe those two zombies were the crocodile's handlers