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Nu: strength and resonance

Discussion in 'DAT Discussions' started by IdahoDoc, Jan 5, 2009.

  1. IdahoDoc

    7+ Year Member

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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?
     
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  2. Shjfr

    5+ Year Member

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    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...
     
  3. 199868

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    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.
     
  4. joonkimdds

    joonkimdds Senior Member
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    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.
     
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