Nu: strength and resonance

[IdahoDoc]

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So I always get these mixed up... if a Nu: has more resonance does that better/stronger Nu: then one with out any resonance?

 

[Shjfr]

I'm pretty sure that if the Nu: is resonant then it is less nucleophilic.

Reasoning: nucleophiles donate electrons to make a bond. Resonance is the delocalization of a charge across a molecule. I believe a nucleophile with a more localized charge would be better at donating that charge (electrons) to another molecule because it is concentrated in one area.

I think this is right...

 

[199868]

Usually nucleophilicity goes hand in hand with bascity.

Resonance strucutre will stabilize base, which makes them weaker.

So.... resonance structure -> stable base -> weaker base -> weak nucleophile.

Hope that helps.

 

[joonkimdds]

I think all we have to know for Nu strength is it inc to left of periodic table and either up or down depending on protic or aprotic solutions.