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Jul 11, 2002
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  1. Attending Physician
could someone please tell me how to distinguish the better nucleophilicity of two molecules. These are the things I know so far but I feel like I'm missing something.

Greater Electronegativity=Lower Nucleophilicity


Anions are usually better nucleophiles

But what if we were given two molecules and asked to tell which one was more nucleophillic.

Any help would be appreciated. Thanks


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Jun 16, 2002
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From my Orgo book this is what I could gather:

Nucleophilicity increases:

1) w/ increasing negative charge: NH2(-1) > NH3
2) going from right to left across the periodic table NH2(-1) > OH(-1)
3) going from top to bottom across the period table I(-1) > Br(-1)
4) w/ increasing polarizability (explains 3)
5) when it is less sterically hindered (not as bulky)

Hope this helps. Good luck. :)
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