Is III a weak base because adding an H to destroys aromaticity as well? Odyssey q

[510586]

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should these only be thought in terms of conjugate base, or I'd the reasoning that gaining an H destroys aromaticity correct as well?

 

[DAT Destroyer]

View attachment 193990 should these only be thought in terms of conjugate base, or I'd the reasoning that gaining an H destroys aromaticity correct as well?

Compound 3 is aromatic.....this will not be a base......Forget about IT !!!!!

NEVER DESTROY AROMATICITY !!!!!!!

Compound 1 and 2 can both be bases......however base 1 is better because the electrons residing on the Nitrogen atom are in an sp3 orbital, and can share the electron pair more readily. #2 is not too shabby, but the electrons are in an sp2 orbital and are held a bit tighter.

Consequently,it reflects in its ability as a base......not as good as compound 1.

Hope this helps.

Dr. Romano

 

[510586]

Compound 3 is aromatic.....this will not be a base......Forget about IT !!!!!

NEVER DESTROY AROMATICITY !!!!!!!

Compound 1 and 2 can both be bases......however base 1 is better because the electrons residing on the Nitrogen atom are in an sp3 orbital, and can share the electron pair more readily. #2 is not too shabby, but the electrons are in an sp2 orbital and are held a bit tighter.

Consequently,it reflects in its ability as a base......not as good as compound 1.

Hope this helps.

Dr. Romano

Oh sorry I think the explanation in the back of the text said that its conjugate base was aromatic so it was weak that'd why I asked. I get it now

 

[Ahmadtoo]

Compound 3 is aromatic.....this will not be a base......Forget about IT !!!!!

NEVER DESTROY AROMATICITY !!!!!!!

The passion in your responses is so intense lol