Carbon Just Did WHAT? One Electron Carbon-Carbon Bond (Organic Chemistry)

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  • Опубліковано 25 лис 2024

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  • @totalsynthesis
    @totalsynthesis  Місяць тому +14

    Thank you for watching and thanks to my channel supporters! Some of the references in the slides are trippin' - the video description has the correct ones. www.patreon.com/totalsynthesis | instagram.com/totalsynthesis_official/

    • @Simon_de_Danser
      @Simon_de_Danser Місяць тому

      The compound in the video is not 9,10-dihydrophenanthrene as mentioned in the description/reference.

    • @totalsynthesis
      @totalsynthesis  Місяць тому

      @@Simon_de_Danser that reference is there as I pulled the figure of the paper for the through-bond interaction

  • @GoodBoyWonder
    @GoodBoyWonder Місяць тому +254

    The only appropriate use of "What the Sigma"

  • @afernandesrp
    @afernandesrp Місяць тому +414

    I propose we change the name of LUMO (Lowest Unoccupied Molecular Orbital) to NO-HOMO.

  • @heat_wave5774
    @heat_wave5774 Місяць тому +97

    Yet another property to add to the list of carbon! It pulls off a one electron bond with itself. Impressive!

    • @totalsynthesis
      @totalsynthesis  Місяць тому +17

      Just to be clear the sigma bond is not special, the two electron bond is literally that

    • @heat_wave5774
      @heat_wave5774 Місяць тому +5

      @@totalsynthesis My bad, one electron bond*

  • @assburgers3457
    @assburgers3457 Місяць тому +75

    “I’m happy with not being a physical chemist” made me giggle

  • @SixOhFive
    @SixOhFive Місяць тому +42

    Science is like feeling around in the dark like we are trying to understand and sense what we do not have senses for.

  • @LiborTinka
    @LiborTinka Місяць тому +43

    You can also make a video about magnesium(I) β-diketiminates, or Mg2(nacnac)2 for short. These compounds contain univalent magnesium dimer (!) with a bond dissociation energy of about 45-50 kcal/mol (depending on ligand) - this makes them exceptionally strong reducing agents able to reduce small and poorly polarizable molecules (e.g. CO2). The compounds are stable enough to be handled in powder form despite the presence of a fragile bond.

  • @SodiumInteresting
    @SodiumInteresting 15 днів тому +2

    This and the 6 bonded carbon. Both interesting videos. Keep up the great content!

  • @Sherrawtf
    @Sherrawtf Місяць тому +26

    nooooo i'm falling in another rabithole of science xwx

  • @nilnull5457
    @nilnull5457 Місяць тому +33

    7:57 Am I missing something or does the fluorenone turn into dibenzosuberene?

    • @totalsynthesis
      @totalsynthesis  Місяць тому +17

      Woops forgot two carbons there. You get the gist :)

    • @margodphd
      @margodphd Місяць тому +3

      ​@@totalsynthesis"Oops forgot two carbons" is something I definitely hope my body's biochemistry doesn't ever say😂

  • @driesvanheeswijk1633
    @driesvanheeswijk1633 Місяць тому +7

    Not even gonna watch the video, liked and subscribed for the thumbnail. Amazing

  • @michaelhicks8603
    @michaelhicks8603 Місяць тому +33

    What the actual F??? This is crazy

    • @menjolno
      @menjolno Місяць тому

      um they used iodine not fluorine. i know that calcologens are easy to confuse

    • @menjolno
      @menjolno Місяць тому

      @menjolno um, calcium is niether iodine nor fluorine

    • @Xnoob545
      @Xnoob545 Місяць тому +2

      What the actual C???

  • @user-yw9mw9hv8o
    @user-yw9mw9hv8o Місяць тому +1

    Using these auxilliary structures to map out the edges of electron-atomic behaviour is what i see more from inorganic chemists than physical chemists tbh. Super fascinating!

  • @herwew7476
    @herwew7476 Місяць тому +13

    There is a very small error in the synthesis, you show Flourenone but it should be dibenzosuberenon. But very interesting nevertheless, great video!

    • @totalsynthesis
      @totalsynthesis  Місяць тому +2

      Yeah my brain was somewhere else while drawing that haha

  • @htomerif
    @htomerif Місяць тому +2

    I really don't know enough about chemistry to make sense of this but I always wondered what kind of weird bonds you could make between the two rings of ferrocene. The distance between the rings seems to be 3 ish angstroms? Maybe the iron being there would prevent any interesting bonds between the rings nearby.

  • @jayglenn837
    @jayglenn837 Місяць тому

    I got super excited because I thought this was diatomic carbon at first, but this is just as interesting!

  • @Jacobk-g7r
    @Jacobk-g7r Місяць тому

    Differences sharing through relativity and as we look deeper between differences dimensions, we see the relatives that allow for such bonds.

  • @titan1070
    @titan1070 Місяць тому +2

    I love the thumbnail

  • @ChemicaLove
    @ChemicaLove Місяць тому +1

    I've seen some one e- C-Al bonds "Hypercoordinate Carbon Chemistry"

  • @markedis5902
    @markedis5902 Місяць тому +8

    4:23 1b & 1c look like some satanic skeletal Mickey Mouse

  • @Nah_Bohdi
    @Nah_Bohdi 19 днів тому +1

    Fascinating.

  • @fauxpassant
    @fauxpassant Місяць тому +3

    8:43 ...and struck gold. Or carbon.

  • @shuanlive
    @shuanlive 27 днів тому

    Thanks for the interesting video. The reference at the end of the video (9:58) looks like a typo.

  • @bengoodwin2141
    @bengoodwin2141 Місяць тому +1

    I would have thought a single bond would always be unstable, and only happen if a molecule didn't have enough electrons due to an atom being ionized. I guess reality is more complicated than that

    • @totalsynthesis
      @totalsynthesis  Місяць тому

      Why so? Single bonds are rather stable generally

    • @bengoodwin2141
      @bengoodwin2141 Місяць тому

      @@totalsynthesis I think I used the wrong word. My understanding of chemistry is only from high school several years ago, but I thought that, for example, if you had an H+ ion, it would bond to a loose hydrogen atom, but the pair of atoms would have 1 fewer electron than it should, so it would suck up the next stray electron nearby and become normal H2. I assumed any one electron bond (what I meant by single bond, if that's the confusion) would work that way.

  • @1.4142
    @1.4142 Місяць тому +1

    I am finally understanding the videos

  • @mansamishra9323
    @mansamishra9323 Місяць тому

    This is crazy work bro 😢

  • @grgvv
    @grgvv Місяць тому +2

    TBF there are doubts about the computational chemistry calculations behind the paper, as it appears that the computations could be incorrect...

    • @ricardosefa4186
      @ricardosefa4186 Місяць тому

      At 7:43 how did the second reaction happen and is there a general name for that step with the weird ketone

    • @totalsynthesis
      @totalsynthesis  Місяць тому +1

      Thanks for raising! Hopefully time will tell if this is just cherry picking or worse. I would assume if it's in Nature and practitioners (like Guy Bertrand) comment positively, it shouldn't be made up

    • @totalsynthesis
      @totalsynthesis  Місяць тому +1

      It's just a nucleophilic addition to the ketone - though the ketone ring structure is missing two carbons at the bottom (woopsies)

  • @strade601
    @strade601 Місяць тому +13

    What the sigma

    • @bitonic589
      @bitonic589 Місяць тому

      Why.. just why???

    • @AnKangaru6005
      @AnKangaru6005 Місяць тому

      ​@@bitonic589erm

    • @50Steaks68
      @50Steaks68 Місяць тому

      @@bitonic589to appeal to the youngins. This video probably has horrible retention because the target audience doesn’t match the thumbnail.

    • @SentientNebula
      @SentientNebula Місяць тому

      Olddd

  • @ruperterskin2117
    @ruperterskin2117 Місяць тому

    Cool. Thanks for sharing.

  • @ciclohexeno2617
    @ciclohexeno2617 Місяць тому

    I remember that the octafluorocubane with an electron in it paper plucked an e- from the bond in the middle of 2,2,3,3 tetramethyl butane with gamma radiation. What about that bond between the 2 t-butyl groups?

  • @황지호-f6i
    @황지호-f6i Місяць тому +1

    06:28 Where did you got this diagram from? I've tried to find it, but it's also not in the video's right corner reference.

    • @totalsynthesis
      @totalsynthesis  Місяць тому

      The right ref is in the description, sorry! 9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior | Molecules 2017, 22(11), 1900

  • @a_8764
    @a_8764 Місяць тому

    Carbon Situation Is Crazy

  • @williamine
    @williamine Місяць тому +4

    man i really wish i could understand most of this. it seems very interesting but the majority of it goes straight over my head

  • @vegbetle
    @vegbetle Місяць тому +2

    ketone at 8:00 seems wrong.

    • @maximus_stp
      @maximus_stp Місяць тому +2

      Nice catch, I was just about to comment the this as well. Should be 7 membered ring instead of 5

    • @totalsynthesis
      @totalsynthesis  Місяць тому +1

      Yea I just typoed that

  • @NikitkaDreamer
    @NikitkaDreamer Місяць тому +4

    hooray for more cursed chemistry!

  • @giovannimerlo1227
    @giovannimerlo1227 23 дні тому +1

    Where's my crown? (Crown ether)

  • @Stinky_Fist_The_Black_Dragon
    @Stinky_Fist_The_Black_Dragon Місяць тому

    W Head-Gordon reference

  • @FoxDog1080
    @FoxDog1080 Місяць тому

    Did you find one in Silicon already

  • @Anik_Sine
    @Anik_Sine Місяць тому

    So is it like a dative bond, but the donor shares 1 electron instead of 2?

  • @vdate
    @vdate Місяць тому +7

    What?
    No. NO. No!
    That's illegal. Knock that shit off, carbon.

  • @magnesiumswift
    @magnesiumswift 27 днів тому +1

    Carbon is gonna do anything at this point 😭😭😭

  • @thiagofeliciano6090
    @thiagofeliciano6090 Місяць тому +7

    Yet no one is talking about ligma😭

  • @KwK-c7t
    @KwK-c7t Місяць тому +1

    You slapped me the nice way 😅 what a chemical punch 👊
    Thanks 👍

  • @hazelmam_
    @hazelmam_ Місяць тому

    the video could end at the first sentence "forget everything you know" and then suddenly 14k viewers are dissociating

  • @jasongarcia2140
    @jasongarcia2140 Місяць тому

    Highest occupied molecular orbital

  • @Kishblockpro
    @Kishblockpro Місяць тому

    isnt this just the same thing as a coordinate covalent bond?

  • @UK1987.
    @UK1987. 8 днів тому

    (The paper was published in Nature)

  • @mutated__donkey5840
    @mutated__donkey5840 Місяць тому +1

    Yeah it’s cool but with this extremely specific scenario which it happens is there any real use?

    • @totalsynthesis
      @totalsynthesis  Місяць тому +1

      No but it might help us understand chemistry and physics a bit better - and then that compounding knowledge turns into something useful at some point

  • @ThePleasantDevourer
    @ThePleasantDevourer Місяць тому

    …were these observations used to elucidate on the equations of entropy or naw?

  • @gruntonium1669
    @gruntonium1669 Місяць тому +2

    Recently started learning about the sigma bond stuff in chem class, and i must ask: what the sigma?

  • @atulshukla9776
    @atulshukla9776 Місяць тому

    Le MOT

  • @razi_man
    @razi_man Місяць тому

    The sigma bond.

  • @Animal-yb1rr
    @Animal-yb1rr Місяць тому +2

    it looks like an animal head shape

    • @SixOhFive
      @SixOhFive Місяць тому +3

      Like a goat or ram or deer with antlers.

    • @zsewqthewolf1194
      @zsewqthewolf1194 Місяць тому

      @@SixOhFivedid….. did we found santin????

  • @LunamLegionam
    @LunamLegionam 20 днів тому +1

    what the sigma

  • @Redstoner34526
    @Redstoner34526 Місяць тому

    Where the sigma?

  • @Speed001
    @Speed001 Місяць тому

    Erm, what the sigma?

  • @mihaleben6051
    @mihaleben6051 Місяць тому

    Wha-what.

  • @septemberhakurei
    @septemberhakurei Місяць тому

    Erm, what the Σ? 😂😂

  • @bobbyshen7826
    @bobbyshen7826 Місяць тому

    Damn, why is it asymmetric, around 9:30?

  • @goiterlanternbase
    @goiterlanternbase Місяць тому +1

    Could you please not monetize your video? You won't make any money here anyway, but the second ad break in 8 minutes is annoying the heck out of me.

    • @abnormality00
      @abnormality00 Місяць тому

      what the fuck?

    • @ts-wo6pp
      @ts-wo6pp Місяць тому

      This is the most German thing I've ever read. Knew you were German when I only saw your channel tag. Germanness exuding out of ever word.

    • @totalsynthesis
      @totalsynthesis  Місяць тому +2

      UA-cam puts these in anyways mate, I dont make the rules

    • @goiterlanternbase
      @goiterlanternbase Місяць тому +1

      @@totalsynthesis Just say a few curse words or something about Po the bear, in the first seconds. Bam. Demonetized😉

    • @abnormality00
      @abnormality00 Місяць тому +2

      @@goiterlanternbase even if they got demonetized, you will still get ads.