29 Replies
@Dexter
Note for OP
+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.I get the concept of partial positives and negatives forming because of resonance
But what does aromaticity have to do with anything
This has a huge dipole moment. Like 7.6 debye iirc
holy shit 💀
why on earth tho
Mb mb it's 4.6
Calicene
Calicene or triapentafulvalene is a hydrocarbon of the fulvalene class with chemical formula C8H6, composed of a cyclopentadiene ring and a cyclopropene ring linked by a double bond. Its name is derived from the Latin calix meaning "goblet", from its shape.
Charge separation makes it really damn stable.
And it's large enough to facilitate pretty large scale electron displacement.
I guess because more the charge difference, more would be the aromatic character?
Since it is already aromatic
Top 500 right?
there is increased delocalization of electrons
it technically not partial its complete -ve and +ve which is very stable cause of aromaticity
yeah true mb its not a partial charge in the traditional sense
now i don't know why antiaromatic compounds are less stable, but why does aromaticity imply more delocalisation
resonance doesnt care about whether the ring has (4n+2) or 4n pi electrons does it
ah what?
didnt get that
could the same thing not be said for (2) and (3)
Second one gets an anti-aromatic part so immediately discount it. Third one is in resonance on one side, but not aromatic. Two aromatic rings trumps everything.
but we aren't judging stability
we're judging dipole
The others are less likely to have charge separation because that reduces their stability.
so if a system is anti aromatic, charge distribution/resonance reduces their stability?
Yes. That's why they don't like existing.
got dark real fast
ok lemme think about this
1st option has no reso shenanigans its just kinda there
2nd option has 1 anti aromatic and 1 aromatic (if we count the middle pi bond as being part of one of the rings in resonance)
3rd option is non aromatic both sides since complete conjugation lacking at the tips
4th option is 1 aromatic and the 2nd also aromatic (counting the middle pi as being part of the right, like they've done in the solution)
verify?
also when one ring is anti and one ring is aromatic, what's the net nature
1st one does have reso shenanigans actually. Double bond is forcing two bonds to be in plane, but the third bond is actually partial out of plane.
oh huh
that causes resonance, how?
or did you just mean the double bond is causing weird things to happen
Remember dancing resonance?
ahhhhh
that explains it
Yeah, so actually I think that's the second highest dipole moment there
wow
ill have to look up why aromaticity conditions are a thing
4pi electrons, (4n+2)pi electrons
what it even means to be aromatic and why
regardless, this makes sense now thank u
It's a nice revision of electronic effects lol
+solved @Opt
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