In nitrogen inversion, the lone pair changes its direction continuously.

Does this in any way delocalize the charge density on the nitrogen making it less nucleophilic and less basic than, say, a bridgehead nitrogen?

Consider the specific case of quinuclidine and triethylamine. Which will be more nucleophilic among them and why?

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    $\begingroup$ Related, maybe almost a duplicate, but not quite as it doesn't ask about nucleophilicity: Does nitrogen inversion affect the basicity of amines? $\endgroup$ May 10, 2019 at 13:30
  • $\begingroup$ related to chemistry.stackexchange.com/questions/38749/… $\endgroup$ May 10, 2019 at 13:35
  • $\begingroup$ @orthocresol yes, I read that. Didn't find the answer too satisfying. It is too vague. $\endgroup$
    – user226375
    May 10, 2019 at 14:16
  • $\begingroup$ @user226375 I have the same question too. Even in electrostatic maps the negative charges looks like its located above the nitrogen but no density below. Have you find an answer? $\endgroup$
    – ado sar
    Oct 13, 2020 at 8:44
  • $\begingroup$ Idk why this was overlooked, but please note that quinuclidine does NOT have a bridge head carbon. The bridge head atom is a nitrogen atom. $\endgroup$ May 18, 2023 at 8:11


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