Short background
As it is known there are interactions between:
- Charges
- Charge and dipole
- Hydrogen bonding
- van der Waals (VDW) forces
From stronger (1) to weaker (4).
VDW forces are divided into dipole-dipole, dipole-induced dipole, induced-induced dipole; also from stronger to weaker.
The problem
Reading about solutions I found interesting the intermolecular forces involved on aniline and dichloromethane mixing. Below both structrures are shown:
Question
What is the most important intermolecular force between those molecules and why? It might be interesting to see an AIM analysis of aniline, but I have no idea how to do that. Also, I'm not sure about what experiment could give valuable information on this case.
My attempt
Those previous interactions aren't mutually exclusive. $\ce{-NH2}$ might be a negative density region of the molecule (inductive attraction), but it is also donor by resonance, so the ring has partially a negative charge density. In consecuence, it is not easy to see the dipole. Dichloromethane, on the contrary, is an easy-to-see dipole.
It might result that London dispersion is the most relevant interaction here, but I can't very well justify it.