Nucleophilicity

[SunChip]

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It's been awhile since I took organic. Can anyone explain to me why electronegativity reduces nucleophilicity? I understand a less bulky base is a stronger nucleophile than a weak bulky bake. Thanks in advance!

 

[loveoforganic]

Could you give two examples? Like, are you thinking of comparing say, the conjugate bases of ethanol and ethanethiol?

 

[SunChip]

"When comparing two elements in the same period, the element further to the right is more electronegative and holds its electrons closer to its nucleus. The less electronegative element is more "willing" to give up its electrons to form a bond, with either hydrogen or carbon."

Is this saying that the farther away the electrons are from the nucleus, the more likely the element will bond with another element, right?

 

[loveoforganic]

Essentially yeah. Less protons in the nucleus of an atom with an electron cloud of the same energy level means those electrons are going to be held less tightly. So something like ammonia is going to be more electron donating than water.

 

[SunChip]

Thanks, Loveoforganic!