Wednesday, July 29, 2009

Iterating a 5D solubility space

About three weeks ago I described how we are mapping a 5D solubility space (mixtures of 4 solvents and temperature). Andrew Lang has been re-running his code to populate the DoSol request sheet with the most useful next measurements. After a few iterations of Marshall Moritz doing experiments and combining with any existing data from the literature we now have 76 measurements for the solubility of 4-nitrobenzaldehyde in mixtures of chloroform, acetonitrile, toluene and THF within the temperature range of -25 to 40 C.

We are now working on ways of quantifying how well we have covered the space and how confident we are of specific predictions. At some point we would like to generalize the predictions based on molecular descriptors of the solvents.

The existing dataset can be sliced in some interesting ways. For example, using Mathematica, Andy has created a plot of the solvent combinations giving the highest possible solubilities of 4-nitrobenzaldehyde at a given temperature. At room temperature this corresponds to a mixture of 38% chloroform and 62% acetonitrile (molar ratio). Below 10C, toluene enters the mix to obtain maximum solubility. At no temperature does THF help.

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At 4:11 PM, Blogger gyg3s said...

This work is extremely interesting.

Have you thought of mapping a resolution using the method of Pope and Peachey?

Or investigating the Dutch resolution?

I'd be keen to see the results of that!

At 4:49 PM, Blogger Jean-Claude Bradley said...

Gyg - chiral separation is an interesting twist. Our Ugi products are generally obtained as racemic mixtures. At some point we could investigate these resolution approaches.

If you have a specific experiment in mind feel free to add it to the DoSol Sheet (link in blog post). If we have the materials and some time we'll see if we can try it.


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