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Topic: What's NH3 as a leaving group?  (Read 3503 times)

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Offline trainee

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What's NH3 as a leaving group?
« on: October 16, 2017, 08:17:11 PM »
I thought NH3 would be a terrible leaving group because it's so basic but apparently it's a better leaving group than water. Can someone clear this up? I was holding the pka values as guidelines with lower pka = better LG
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Offline Babcock_Hall

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Re: What's NH3 as a leaving group?
« Reply #1 on: October 16, 2017, 09:14:10 PM »
Both species are polyprotic, and one should specify which protonation state (and which pKa) one means IMO.
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Offline Enthalpy

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Re: What's NH3 as a leaving group?
« Reply #2 on: October 17, 2017, 09:32:42 AM »
Could his relate with the C-N bond being weaker than C-O?

kJ/mol
391   HO-C2H5
352   H2N-C2H5
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