How Chemists Make Carbon 2+ (Octet Rule: Violated) | Organic Chemistry & Synthesis
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- Опубліковано 1 чер 2024
- Yep, you're looking at a carbon with four valence electrons. How can such an unfavorable species be synthesized, how is it stabilized, and how does it behave? Watch this video to learn exotic chemical reactions and unique properties and geometries - which you likely have never seen before!
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00:00 Carbon 2+, your teacher doesn't know about it
00:32 Octet rule basics
01:03 Synthesis of the carbene precursor
03:10 Synthesis of carbon 2+ (doubly oxidized carbene)
04:45 Electronic and steric stabilization
05:41 Geometry of carbon 2+ and cumulenic orbitals
06:51 Reactivity of the doubly oxidized carbene
08:15 Conclusion
Key references:
- An Air-Stable “Masked” Bis(imino)carbene: A Carbon-Based Dual Ambiphile | JACS 2023, 145, 2064
- A crystalline doubly oxidized carbene | Nature 2023, 623, 66 (Chemrxiv: doi.org/10.26434/chemrxiv-202...)
- Controlling Möbius-Type Helicity and the Excited-State Properties of Cumulenes with Carbenes | J. Phys. Chem. A 2020, 124, 10100
Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures) - Наука та технологія
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Attended Prof. Bertrand's seminar a few days ago. The motivation was simple - you have stable carbenes and why not oxidizing them. His discoveries were crystal clear, only to recognize how challenging and tedious to materialize them. :)
Aah, the shiny orbitals fron IboView @ 6:41.
*Chef's kiss
very illegal
Amazing video! Would love to see more on inorganic/organometallic stuff, as well as molecular orbitals. Thanks :)
Unreal 😮
Your content is just 🔥
🙏
Excelletn explanation of this complex paper
Thanks!
This topic is cool
Pretty fire compound
I'm enjoying this ty
Great to hear!
Well many compounds violate the octet rule - periodic acid is one such example commonly presented. Wasn't the existence of such compunds the initial motivation for building molecular orbital theory? It's like the theories of acids: Arrhenius -> Brondsted-Lowry -> Lewis (sorry for ommiting diacritics - lazy)... Each theory is useful to a point. In the end it's all quantum physics and that is difficult if not impossible to compress into few rules of thumb - this is why there are always exceptions in chemistry.
This reminds me of an old paper I've read where researches calculated Gibbs free energies for several possible ligand exchanges on a single octahedral complex of magnesium only to find out which one is more likely. The computation was done on a CRAY-Y supercomputer ... and that's just a single complex of a single element in a single oxidation state... This made me understand why quantum computers are such a hot topic in certain areas.
Yes, obviously many compounds and I agree with your perspective. But I think it's pretty crazy that we can create a carbon with 4 valence electrons nevertheless!
@@totalsynthesis Indeed. Unfortunately, it will take me many dozens of hours of study until I will be able to appreciate this :( Bookmarking your video for this possible future...
I don't agree with that perspective at all. It's all nonsense in my view. All molecules comprise nuclei that behave on the scale of molecules as electrostatic point charges, and electrically charged electrons exist as charge and current densities that obey Maxwell’s equations, and the binding is determined by electrical and electrodynamics forces. Nothing in chemistry is indeterminate. Nothing in chemistry requires quantum computers. I am trying to understand what is going on here so I may be able to explain things in a better way. Unfortunately, the chemistry is beyond my working knowledge. But the physics is exactly what I am interested in. I don't understand how scientific minds can look at the mess called modern quantum physics and see anything scientific about it. It's a complete disaster in a scientific view.
I wish Mr TS would try to avoid giant complex molecules if possible and put forth the most simple example possible to demonstrate his point, and then stop. Then we can break down the physics. Unfortunately, these comments do not allow more than basic math. I don't like the term steric effects either. It's so vague.
Very nice,
I wonder how much of the + charge really rests on that central carbon, as calculated.
Isn't another resonance form just a carbodiimide, attached to two iminiums? What's so special about this? I'm wondering.
This is the epitome of a cursed molecule.😮
And I thought regular carbenes were weird