[blueblueblue]

Hello!  I was hoping to get some of your input on the following question:

There are 2 nitrogens in Tamiflu.  Which is more basic and why?


I think the top nitrogen has an ether group attached to the adjacent carbon that delocalizes and induces electrons.  Since oxygen is very electronegative a lone pair of nitrogen has more positive charge.  On the other hand, primary nitrogen is one carbon away, farther than the ether group so it does not have as much of an effect as the first nitrogen.  The lone pair on that nitrogen can accept a proton better than the first nitrogen.

The definition of a Bronsted-lowry base is it accepts an H+ proton, so the second nitrogen can accept a proton better than the first.  So, it is the more basic one.

[Schrödinger]

You're right about the fact that the NH₂ Nitrogen is more basic than the one on top. And the reasoning is quite accurate too.

But the functional group that is adjacent to the nitrogen on top is a ketone, not an ether

[kingsfan]

one of nitrogen is primary amine, strong base
second -amide is very week base

[blueblueblue]

Thank you both for your help with this.

I also need to draw the conjugate acid of these two nitrogens.  Will the nitrogen with the ketone group, on the top, have proton H+ or will the oxygen have it? 

It seems that ketone is a strong negative oxygen and that stabilizes the conjugate acid (or this base is already stabilized with the double bond).