New answers tagged amines
7
The product at the para-position is more stable as it allows the compound to exist in the quinoid form, rather than only in the benzoid form:
This is important as in your case, if the substituent $\ce{X}$ is $\ce{H}$, then depending on the solvent, as much as 89% of it may exist in the quinoid form ($\bf{2}$).
References:
Satoshi Kishimoto, Shinya Kitahara,...
1
When a 1° amine attacks to a carboxyl group, The structure below (left) is generated which lowers the energy level of the intermediate such that the second amine can easily react with the other carboxyl group.
It is clear that 2° amines (right) don't have such proton for hydrogen bonding with the oxygen. Why the second 2° amine doesn't attack to the other ...
5
The mixing of two compounds is a process which requires consideration of three types of interactions: solute-solvent, solvent-solvent and solute-solute. You make a good argument for the solute-solvent interaction being stronger in mixtures of butanamide and water, compared to butylamine and water. However, as you say, this argument alone would predict a ...
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