Evan Curtin from the Bradley Research Group at Drexel University presented a poster at the Research Day for the College of Arts and Sciences on April 5, 2011. The project involves the synthesis of aromatic imines and the measurement of their solubility to select an optimal solvent for their formation.

2. The supernatant will be saturated

3. Find a solvent in which the reactants are soluble and the products insoluble

4. Run the reaction

5. Simply filter to get a pure product

7. Solubility of benzalaniline in ethanol was found to be 1.3M

9. Online web service created by Professor Bradley (Drexel, Philadelphia, Pennsylvania) and Professor Andrew Lang (Oral Roberts University, Tulsa, Oklahoma)

10. Uses a Googledocs spreadsheet, available to the public

11. Create a saturated solution of solute in a solvent

12. Obtain HNMR spectra of the saturated solution

13. Upload the spectra in JCAMP-dx format

14. Specify solute and solvent peaks, and the number of corresponding H’s

15. Enter density and molar mass for the solute and solvent (predicted densities from Chemspider.com are commonly used for solids)

16. Spreadsheet automatically calculates molarity

17. Life threatening disease caused by the parasite plasmodium falciparum

18. In 2008, there were 247,000,000 cases of malaria and almost 1,000,000 deaths from the disease

20. At the solute’s melting point, the two are assumed miscible

21. During synthesis, benzalaniline was recrystallized in methanol. In order to extract the product, the mixture had to be cooled to precipitate in ethanol. The more substituted imine didn’t have to be cooled to form precipitate

23. When solubility for a solute in 5 different solvents is found, this information can be used to predict solubility in 72 solvents using the Abraham model

24. Test solubility predictions to refine the model

25. Apply the solubility information to optimize syntheses

27. MP of 227-230°C is consistent with impure 4-chlorobenzoic acidBoth of these reactions formed some of the desired imine, but after a cold ethanol wash, there was very little imine remaining Bradley, Jean-Claude and Lang, Andrew. “Open Notebook Science Web Services.” <http://onswebservices.wikispaces.com/> Curtin, Evan. “Synthesis of four imines from vanillin, p-chlorobenzaldehyde, aniline and o-chloroaniline.” <http://usefulchem.wikispaces.com/Exp262> Curtin, Evan “Synthesis of an imine from benzaldehyde and aniline.” <http://usefulchem.wikispaces.com/Exp261> Curtin, Evan. “Determination of solubility of sample 1A from UCExp262.” <http://onschallenge.wikispaces.com/Exp206> Curtin, Evan. “Determination of solubility of sample 1A from UCExp262 in toluene, acetonitrile, THF, and chloroform.” <http://onschallenge.wikispaces.com/Exp207> Gut, Jiri. “Falcipain-2 inhibition results for 2 Ugi products.” < http://usefulchem.wikispaces.com/Exp165> “Malaria Fact Sheet.” World Heath Organization. 2004. <http://www.who.int/mediacentre/factsheets/fs094/en/index.html> <http://onswebservices.wikispaces.com/> Mirza, Khalid Baig. “Synthesis of compounds ranked 55-124 from library DEXP014-V2B” <http://usefulchem.wikispaces.com/Exp181> “Priority Environment and Health Risks.” World Health Organization. 2004. <http://www.who.int/heli/risks/en/> (Ref: “Synthesis of an imine from benzaldehyde and aniline.” “Synthesis of four imines from vanillin, p-chlorobenzaldehyde, aniline and o-chloroaniline.”) (Ref: “Synthesis of four imines from vanillin, p-chlorobenzaldehyde, aniline and o-chloroaniline.”)