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The pKa of the compound on the left is 4.27, would the pka of the compound on the right be larger due to the ketone groups?
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chemistryisnt sciense
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>>8207777
Considering the carbons that would normally stabilize the charge are more electron deficient I would say the pKa would go down

Also we are talking about the pKa of the conjugate base here........right
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>>8207811
conjugate acid, with the nitrogen's protanted
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>>8207827
oh gee yes thats what I meant

anyway so what I said, I think it goes down. The compound becomes a weaker base. The conjugate acid is less stabilized.
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Isn't the fact that the ketone is basically in the meta position, actually has the opposite effect and does not increase the stability, even if it's an EWG?
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>>8207794
get off this board faggot
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>>8207777
i'm with >>8207836 the basicity of those N's would decrease so the pKa will go down
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>>8207836
>>8209368
this. oxygen is more electron withdrawing and will polarize the compound as well. this will make the conjugate acid more acidic which means lower pKa
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>>8209368
>>8207836
I'm inclined to agree with you guys because the resonant structures are all sorts of fun for the left compound, but the ketones kind of limit the number of potential resonant compounds available. Not to mention the most delocalized scenario resonant structure for the right compound involves having a negatively and positively charged nitrogen and a negatively charged oxygen.
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>>8210653
>Not to mention the most delocalized scenario resonant structure for the right compound involves having a negatively and positively charged nitrogen
Can you give us a pic?
Thread replies: 11
Thread images: 1

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