[Messi]

What would you say is more nucleophilic... benzylamine or dibenzylamine? I am just curious I tried googling but didn't find a response

[sjb]

What would you say is more nucleophilic... benzylamine or dibenzylamine? I am just curious I tried googling but didn't find a response

What measures of nucleophilicity do you know?

[Messi]

What would you say is more nucleophilic... benzylamine or dibenzylamine? I am just curious I tried googling but didn't find a response

What measures of nucleophilicity do you know?

Well I know that alkyl groups are electron donating so I would expect the dibenzylamine to be more nucleophilic than benzylamine, no?

[Babcock_Hall]

Messi, How does one measure nucleophilicity experimentally?

[Messi]

Messi, How does one measure nucleophilicity experimentally?

By measuring the rate of reaction by different nucleophilic based on a set standard. The thing is would benzylamine be more nucleophilic due to less bulk or would dibenzylamine be more nucleophilic due to the electron donating nature of alkyl groups and dibenzylamine has more alkyl groups attached to itself.

[Babcock_Hall]

Unfortunately, the closest comparison I could find was diethylamine versus triethylamine, and the former is slightly more nucleophilic.

[Messi]

Unfortunately, the closest comparison I could find was diethylamine versus triethylamine, and the former is slightly more nucleophilic.

Why though? Because of sterics?

[Babcock_Hall]

That would be my best guess.  You might look around for a good physical organic textbook for further information.

[orgopete]

I find this difficult to predict a priori. I think of an aryl group as electron withdrawing as in aniline, but that isn't the question. However, it is a substituent on a methyl group.

Although not necessarily an indication of nucleophilicity, I would compare the pKa values. If dibenzyl is more basic, then I would expect more nucleophilic.