Nucleophilicity and basicity of compounds with or without nitrogen inversion

Asked May 10 '19 at 12:56

Active May 19 '23 at 13:48

Viewed 360 times

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?

edited May 19 '23 at 13:48

Mithoron

asked May 10 '19 at 12:56

user226375

1

Related, maybe almost a duplicate, but not quite as it doesn't ask about nucleophilicity: Does nitrogen inversion affect the basicity of amines? – orthocresol May 10 '19 at 13:30
related to https://chemistry.stackexchange.com/questions/38749/does-amine-inversion-affect-basic-strength – Chakravarthy Kalyan May 10 '19 at 13:35
@orthocresol yes, I read that. Didn't find the answer too satisfying. It is too vague. – user226375 May 10 '19 at 14:16
@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? – ado sar Oct 13 '20 at 08:44
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. – Sage of Seven Paths May 18 '23 at 08:11

0 Answers0