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the claim
The conjugate base of pyrrole is resonance stabilized
the verdict
REFUTED
the evidence says no
refutedsupported
the weight of evidence
0 sources for · 1 against
AS REPORTEDno primary record reached; this is what the reporting says

Chemical discussion indicates that the conjugate base of pyrrole lacks a reasonable amount of resonance stabilization due to the orientation of its lone pair orbital.

Evidence against · 1
Is the conjugate base of pyrrole resonance stabilised?
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# Is the conjugate base of pyrrole resonance stabilised? - Tags: organic-chemistry, acid-base, aromatic-compounds, heterocyclic-compounds - Score: 7 - Views: 1,987 - Answers: 2 - Asked by: gamma1 (1,130 rep) - Asked on: Jun 5, 2017 - Last active: Jul 12, 2017 - License: CC BY-SA 3.0 --- ## Question This is something I am conceptually struggling with, if I deprotonate pyrrole on the nitrogen in the ring, is it true that the conjugate base is not resonance stabilised, because the orbital is orthogonal to the ring? However, with a p_K_a of 23, I feel like it must have some resonance stabilisation. [![enter image description here](https://i.sstatic.net/yF6Fg.png)](https://i.sstatic.net/yF6Fg.png) [![enter image description here](https://i.sstatic.net/BWZNC.png)](https://i.sstatic.net/BWZNC.png) --- ## Answer 1 — Score: 3 - By: Martin - マーチン (45,215 rep) - Answered on: Jun 12, 2017 There is like you assumed no reasonable amount of resonance stabilisation. However, the aromatic π-system contributes to the stability of σ-skeleton. Below you can find the MO of pyrrole and its N-deprotonated anion (click it to enlarge). You can see that in MO 17 the electron density is shifted fu
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rails:sufficiency:refuted:single_source:for=0+0p:against=1+0p | v55:sufficiency

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