Researchers

Hai Truong and Khalid Mirza

Objective

To find the affect of imminium (of phenanthrene-9-carboxaldehyde+ furfurylamine+phenylacetic acid) on the solubility of the Ugi product UCExp17C in benzene.
Co-solutes
a) phenanthrene-9-carboxaldehyde+ furfurylamine+phenylacetic acid (0.5M, 0.3M, 0.1M, 0.08M, 0.06M and 0.04M) in both benzene and methanol


Procedure

A) 152A- 0.5M : Weigh out fufurylamine (2.5mmol, 243mg) in a 5mL volumetric flask. Add a small volume of benzene to it. Then weigh out phenanthrene-9-carboxaldheyde (2.5mmol, 516mg) and add it to the amine/benzene solution, This is imine/benzene solution. Then weigh out phenylacetic acid (2.5mmol, 340mg)and add it to the imine/benzene solution. Make it up to the mark with benzene. Use this as a stock solution- 152A.-0.5M

Perform dilutions
152B - 0.30M- Pipette out 600uL of 152A in to a 1mL volumetric flask and make it up to the mark with benzene
152C - 0.10M - Pipette out 200uL of 152A in to a 1mL volumetric flask and make it up to the mark with benzene
152D - 0.08M - Pipette out 160uL of 152A in to a 1mL volumetric flask and make it up to the mark with benzene
152E - 0.06M - Pipette out 120uL of 152A in to a 1mL volumetric flask and make it up to the mark with benzene
152F - 0.04M - Pipette out 80uL of 152A in to a 1mL volumetric flask and make it up to the mark with benzene

Apart from these samples also run blanks with just benzene and Ugi product UC176C (2 runs)



Results

Spreadsheet ONSCExp152-ii

Discussion


Conclusion


Log

12-04-2009
12:02 In 5mL volumetric flask, weighed out exactly 243mg fufurylamine in the flask. Added small amount of benzene.
12:10 Weight out 516mg phenathrene-9-carboxaldehyde and put into the 5ml flask above. Added small amount of benzene. At this point, the solution is the flask is amine/benzene solution.
12:15 Weight out 340mg phenylacetic acid and added to the 5ml flask above. Added more benzene to make it to the mark. This solution (in 5ml volumetric flask) is labeled 152A- 0.5M as stock solution
12:30 Took out five 1ml volumetric flasks. Label from B,C,D,E,F.
12:35
In flask B: pipetted out 600uL of 152A in to flask B and make it up to the mark with benzene. The concentration of solution is 0.30M
In flask C: pipetted out 200uL of 152A in to flask C and make it up to the mark with benzene. The concentration of solution is 0.10M
In flask D: pipetted out 160uL of 152A in to flask D and make it up to the mark with benzene. The concentration of solution is 0.08M
In flask E: pipetted out 120uL of 152A in to flask E and make it up to the mark with benzene. The concentration of solution is 0.06M
In flask F: pipetted out 80uL of 152A in to flask F and make it up to the mark with benzene. The concentration of solution is 0.04M
12:50 Took out 8 half dram vials and labeled A,B,C,D,E,F,G and H. Then
For vial A: put 500ul of solution 152A into vial A and put small amount of Ugi 176C so that there are still some solid remained in the solution.
For vial B: put 500ul of solution from flask B into vial B and put small amount of Ugi 176C so that there are still some solid remained in the solution.
For vial C: put 500ul of solution from flask C into vial C and put small amount of Ugi 176C so that there are still some solid remained in the solution.
For vial D: put 500ul of solution from flask D into vial D and put small amount of Ugi 176C so that there are still some solid remained in the solution.
For vial E: put 500ul of solution from flask E into vial E and put small amount of Ugi 176C so that there are still some solid remained in the solution.
For vial F: put 500ul of solution from flask F into vial F and put small amount of Ugi 176C so that there are still some solid remained in the solution.
For vial G: put 500ul of pure benzene into vial G and put small amount of Ugi 176C so that there are still some solid remained in the solution. - blank solution
For vial H: put 500ul of pure benzene into vial H and put small amount of Ugi 176C so that there are still some solid remained in the solution. - blank solution
13:20 Parafilmed all vials.
13:45 Put all vials in the Lauda cooling/heating bath. The temperature in the bath is 40C
12-05-2009
11:10 Changed the temperature setting of the water-glycol to 25C.
16:10 Removed the vials from the temperature control bath and centrifuged them...Sample vial 152A had leaked out..the solution in the vial has therefore been discarded.
16:20 Obtained six one dram vials and transferred out approximately 400uL DMSO0d6 in to them and labeled B2 through H2
17:00 After centrifuging the half dram vials B through H, carefully transferred out approximately 200uL supernatant from each into corresponding '2' series vials. The resulting solutions in one dram vials with DMSO-d6 are labeled ONSCExpB through ONSCExp152H
20:45 Completed obtaining HNMRs of the samples.