Trying to better understand Lipophilicity and solubility in water

[modern]

So I've been trying to dive deeper into understanding what leads to insoluble salts and there are a few reasons but Lipophilicity seems to be fairly high. Large molecules and lipophilicity seem quite important.

After researching and comparing online context without opening a textbook seems that Lipophilicity being under the amount of water leads to the compound being insoluble salt.

I have been playing around with playground.calculators.cxn.io and testing different ions to calculate the LogD and it seems that acetate with a ph of 5-6.3pH should in theory be insoluble in water so assuming there is a concentration high enough and clean enough would mescaline acetate form crystal/salt in vinegar water?

That chart is fairly poor but does seems to illustrate expected results for most salt ions. Carbonate with DMT indeed seems impossible due to ph range but Mescaline carbonate shows possible at 7-7.5 pH from freebase so maybe it is possible to produce with water extract?

I've been plugging in a few different acids I want to experiment with and salicylic acid seems promising but I know sometimes in practice it behaves differently.

What else am I missing without just trying it myself in determining if a salt will be insoluble in water? Even if only partially soluble.

 

[acacian]

Interesting thread. I always found mescaline acetate very water soluble. I'm not sure how you would go about getting it to precipitate from vinegar/water solution. Even if you saturated your solution I imagine a large portion would still remain dissolved. Curious as to your thoughts on how you might be able to get it to precipitate?

 

[modern]

I don't know exactly how lipophilicity actually plays into this or if even possible. My chemistry knowledge is severely lacking but from my understanding it should be possible but probably some other factor I'm unaware of.
I would assume that at a high enough concentration (perhaps not viable for extractions) if you can carefully add a more concentrated acetic acid via titration you can get the mescaline acetate to precipitate/crystalize. Maybe vinegar is just to diluted?

From my research lipophilicity is a big factor in solubility and mescaline is a fairly large molecule so that is my understanding on the topic.

EDIT: There has to be another factor since citrate based on that chart should also be insoluble in water

EDIT 2: I'm actually interpreting this wrong and the value should be above the water so these are show solubility in water so this is actually NOT what I want. I'll test to see if I can make the salt in this...

 

[Transform]

The trouble with acetic acid is that, in pure form, it is also a solvent - glacial acetic acid - so attempts to precipitate mescaline acetate by adding acetic acid may not go as modelled, unless you start increasing the complexity of the model. Some of the contradictions you've observed may be down to a mistaken interpretation of what the chart indicates.

There's a very good text on solvents and crystallisation that may be tucked away on the forum somewhere. One of the more infrequent advanced chemists may remember the title, but I can only dig it out of my personal files next week, so I'll put this on my To Do list.

As far as mescaline and lipophilicity goes, its three methoxy groups add polarity to the molecule which appears to contribute to the water-solubility of the freebase. Lipophilicity mostly refers to a substance's tendency to dissolve in nonaqueous solvents (to put it very simply), so naphtha's inability to dissolve mescaline freebase can be interpreted in light of this.

There will be far more to solubility constraints of salts than simple lipophilicity - it's outside my specific areas of expertise to even begin to list the details - but you've chosen a promising area of study here so I'll be keeping an eye on your progress.

What else am I missing without just trying it myself in determining if a salt will be insoluble in water?

In this field, experimental data is king. As alluded to above, there are a large number of factors involved in solubility and crystallisation so I can only encourage you to continue in systematically seeking out and studying the appropriate chemistry texts.

 

[modern]

So while playing around I tried adding a few salts and the chart changed to a seemingly more useful data point. I may have added the salt erroneously at the NH2 and making it O but seems to provide data that seems more useful than the first one.

This is probably not that useful but does reaffirm me wanting to test Salicylic acid seeing number similar to oxalic acid. I'm probably better off just experimenting but it has been a nice time killer. Just finishing up cleaning some salicylic acid so it'll be next months project for me.

Edit the molecules form left to right for colors
oxalate, sulfate, salicylate, benzoate, nitrate, carbonate, acetate, hypochlorite and freebase
These can be completely wrong so if anyone wants the actual info I suggest doing it themselves.

 

[Transform]

Hypochlorite might be a bit of a poor choice for this experiment
Also, many of your structures are… somewhat divergent from, er, the goals of your research. Several of them are the respective esters of 3,4,5-trimethoxyphenylethanol, and another appears to be the corresponding amide. Salts are formed without the covalent bonds which you depict between the intended cation and anion. As a result, some of your data may be inaccurate or entirely misleading.
Edit: I see you already covered this point

These can be completely wrong so if anyone wants the actual info I suggest doing it themselves

I'll help you out with the structures, no earlier than in a week or two.

 

[modern]

Hypochlorite might be a bit of a poor choice for this experiment
Also, many of your structures are… somewhat divergent from, er, the goals of your research. Several of them are the respective esters of 3,4,5-trimethoxyphenylethanol, and another appears to be the corresponding amide. Salts are formed without the covalent bonds which you depict between the intended cation and anion. As a result, some of your data may be inaccurate or entirely misleading.
Edit: I see you already covered this point

I'll help you out with the structures, no earlier than in a week or two.

I saw the names were off. IDK if you can calculate salts on that website or not but then like I mentioned I'm lacking in chemistry knowledge.
I'll just try to make the salts and test solubility in my used solvents

I appreciate the help. No rush on your end in the mean time I'll keep trying to see if I can represent these correctly.