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Topic: Acid-Base Strengths  (Read 6952 times)

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Offline Winga

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Acid-Base Strengths
« on: July 28, 2005, 05:19:08 PM »
Base:
Me3N, NH3, NF3

Which one is the most basic of the three?
Me3N or NH3?

Offline hmx9123

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Re:Acid-Base Strengths
« Reply #1 on: July 29, 2005, 02:21:51 AM »
Have you attempted this?  What were your findings or initial thoughts?

Offline Winga

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Re:Acid-Base Strengths
« Reply #2 on: July 29, 2005, 05:57:05 AM »
According to my lecture notes, by using inductive effect,

the basicity in descending order:
Me3N > NH3 > NF3

I wonder that H is less electronegative than C (from Me group), but why NH3 is less basic than Me3N.

I know that Me is an e- donating group, but the donation should be through hyperconjugation, right?
There is no empty p-orbital in N and it is sp3 hybridized.



Offline Mitch

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Re:Acid-Base Strengths
« Reply #3 on: July 29, 2005, 06:40:19 AM »
Its an inductive effect not a hyperconjugation effect.
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Offline Winga

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Re:Acid-Base Strengths
« Reply #4 on: July 29, 2005, 08:12:02 AM »
Without hyperconjugation, as C is more electronegative than H, the methyl groups should donate less e- density to N than that of H, so Me3N is less basic than NH3, am I right?

Offline maxyoung

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Re:Acid-Base Strengths
« Reply #5 on: October 05, 2005, 03:23:03 AM »
Although oxygen is more electronegative than nitrogen, nitro group is more electron withdrawing than hydroxyl group, right? Oxidation state also matters when considering inductive effect, since electronegativity changes with oxidation states for an element. It's the same thing that inductive effect follows  F > H > CH3.

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