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Topic: Hello everyone, why is n3- a weak base?  (Read 2710 times)

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Offline Frijolebunny

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Hello everyone, why is n3- a weak base?
« on: October 03, 2020, 12:27:00 PM »
Hello, I am having some trouble understanding why some compounds are weak acids or strong bases/nucleophiles. I was wondering why n3- is a weak base? Its conjugate acid seems stable to me, it has a formal charge of 0. Wouldn't this make n3- a strong base? Or is my logic wrong somewhere? I would appreciate any clarity, thank you!

Offline rolnor

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Re: Hello everyone, why is n3- a weak base?
« Reply #1 on: October 03, 2020, 02:03:48 PM »
I guess you mean azide?
It has several resonance structures so the charge is on all three nitrogens making this a weak base.
https://en.wikipedia.org/wiki/Azide

Offline chenbeier

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Re: Hello everyone, why is n3- a weak base?
« Reply #2 on: October 03, 2020, 03:25:49 PM »
The Problem here is the writing. Correct N3- that is Azid. But if meant N3- is Nitrid.

That is different.

Offline rolnor

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Re: Hello everyone, why is n3- a weak base?
« Reply #3 on: October 03, 2020, 04:09:05 PM »
True, but nitrid would be very strong base?

Offline chenbeier

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Re: Hello everyone, why is n3- a weak base?
« Reply #4 on: October 03, 2020, 04:39:17 PM »
Not Sure, But if I compare Na3N with Na2O what is stronger.
Or NaNH2 and NaOH.
For Nitrid I couldnt find a pKb value

Offline rolnor

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Re: Hello everyone, why is n3- a weak base?
« Reply #5 on: October 03, 2020, 05:41:20 PM »
NaNH2 is one if the strongest  bases, imagine if you take 2 more protons away from it. I have a feeling that nitrides are more covalent compounds, not ionic.

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