Identify the most basic site on this molecule

[Sagan42]

http://imgur.com/EaBMr

I've highlighted what I think is the most basic site. I didn't choose anywhere on the three rings because 1) deprotonation would allow resonance or 2) the Oxygen/ether and the Flourine would cause inductive effects. I also didn't chose the Carbon on the nitrile because I felt it would cause induction - same reasoning for the amine attached carbons. The highlighted area is farthest from EN atoms.

I don't have the answer, but I was hoping someone could give feedback on my reasoning.

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[solitarius]

It's where the Nitrogen is located (the one not in a triple bond).

 

[Sagan42]

It's where the Nitrogen is located (the one not in a triple bond).

I think you might be right. Should I even be looking at the rings or the alkane parts of the structure?

 

[StIGMA]

You seem to be confusing hydrophobic and basic. An alkane chain doesn't have much basic character at all.

Look up 'lewis base' if you still don't get it.

 

[solitarius]

Reasoning is as follows: a lone pair is better than a shared pair. That rules out all the pi bond electrons. This narrows it down to the 2 N's, O, and F. The most basic site will be on the least electronegative atom, ruling out O and F.

Now you're down to the 2 nitrogens. The lone pair on the sp3 nitrogen is further away from the nucleus, making it more shareable.

 

[Sagan42]

http://i.imgur.com/F1mRD.png

I'm also looking at this question, which asks which molecule is most basic. The one in the middle has a lot of inductive effects, and the one on the right has resonance and induction, but apparently the one on the right is most basic. I would have thought the one on the left is most basic.

 

[Winged Scapula]

Since this is not specifically an MCAT question and SDN has a policy of not helping with "homework questions" this thread will be closed in accordance with the TOS.