strength of nucleophiles vs basicity

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Caitlin Dillon 3G
Posts: 26
Joined: Wed Sep 21, 2016 2:56 pm

strength of nucleophiles vs basicity

Postby Caitlin Dillon 3G » Sun Feb 26, 2017 11:38 pm

What is the difference between the trend in how basic something is and how nucleophilic it is?

haleh matinrad 1C
Posts: 17
Joined: Sat Jul 09, 2016 3:00 am

Re: strength of nucleophiles vs basicity

Postby haleh matinrad 1C » Sun Feb 26, 2017 11:58 pm

To my understanding there is no direct general trend for them. Its just the fact that negatively charged species tend to be basic. It's important to remember that the strength of a nucleophile is relative to the reaction it is taking place in.

Chem_Mod
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Re: strength of nucleophiles vs basicity

Postby Chem_Mod » Mon Feb 27, 2017 7:37 am

Typically something that is very basic, ie has concentrated, localized charge, such as a lone pair, will be nucleophilic as well. Something that is basic, but NOT nucleophilic will have a lone pair, but it will be inaccesible due to steric bulk. Imagine trying to deprotonate with hydroxide (OH-) vs. t-butoxide (CH3)3C-O-. They're both very basic, t-butoxide is very large and will have difficulties acting as a nucleophile.


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