While those blocks of text look appealing, neither of them really answer his question.
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Though, it can be simply explained again, with 'like dissolves like'
Not only does this mean that non-polar dissolves non-polar, polar dissolves polar, etc.
It can also be applied if you consider the structures of the solvent and solute in question.
Bring yourself down to the molecular level. The big factor here is electron density. Is there a dipole? Where are those electrons, are they resonant stabilized? Fully saturated?
You'll find that most non-polars will be soluble in a non-polar solvent to some degree, even if its negligible, their solubility will be more apparent at highly increased temperatures.
But i'd like to help you further. Which non-polar solute and solvent were you wondering about? The selectivity of a solvent is often dependent on temperature.
But, lets use DMT as an example, since its fitting.
This the best way I could think of to explain this, i've left out some things, bear with me.
Like dissolves like. Most people use naphtha for extracting freebase DMT, its a mixture of aliphatic hydrocarbons, like heptane and hexane. These are basically fully saturated chains of carbon. Quite non-polar. DMT doesn't really have a great affinity to these aliphatics, because its composed of an aromatic ring, (Indole) giving it a small dipole. (as well as the amine) But, this is actually useful since it allows us to use temperature to our advantage. I.E. Freeze precipitate.
Now, lets take toluene, or benzene, as an example solvent. These aromatic rings are resonant stablized, they are indeed non-polar, but not as much as the fully saturated hydrocarbon, they are de-localized in the aromatic. They have electron densities that are more 'like' that of the freebase DMT molecule.
So it has higher affinity.
This doesn't necessarily make it a better solvent, the best solvent depends on what you want to use it for. If you wanted to freeze precipitate, an aromatic isn't the best choice.
If you wanted to salt out the fumarates, the better solvent would be the aromatic.
Expect nothing, Receive everything.
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