strength of nucleophiles vs basicity
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strength of nucleophiles vs basicity
What is the difference between the trend in how basic something is and how nucleophilic it is?
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Re: strength of nucleophiles vs basicity
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.
Re: strength of nucleophiles vs basicity
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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