Researcher

Hai Truong & Khalid

Objective

To measure the solubility of UCExp176C in 0.1M, 0.2M, 0.3M, 0.5M imine solution in benzene

Procedure

Make-up
0.1M 1000uL imine solution in benzene by dissolving phenanthrene-9-carbaldehyde 21mg in benzene (974uL). To this add fufurylamine (9uL).
0.2M 1000uL imine solution in benzene by dissolving phenanthrene-9-carbaldehyde 42mg in benzene (948uL). To this add fufurylamine (18uL).
0.3M 1000uL imine solution in benzene by dissolving phenanthrene-9-carbaldehyde 63mg in benzene (922uL). To this add fufurylamine (27uL).
0.5M 1000uL imine solution in benzene by dissolving phenanthrene-9-carbaldehyde 105mg in benzene (870uL). To this add fufurylamine (45uL).
If the reaction goes to 100% conc of imine =0.1M, 0.2M, 0.3M, 0.5M.

Calculation-Link

Results

Spreadsheet ONSCExp149-

Discussion

Sample ID
Ugi conc
(M)

aldehyde conc (M)
SAMS estimate

amine conc (M) SAMS estimate
imine conc (M)SAMS estimate
aldehyde at start (SAMS) (M)
(aldehyde+imine)

amine at start (SAMS) (M)
(amine+imine)


% aldeyde
xs

ONSCExp149-1D
0.04
0.06
0.04
0.03
0.09
0.07
28.5
ONSCExp149-2D
0.06
0.09
0.07
0.09
0.18
0.16
12.5
ONSCExp149-3D
0.07
0.1
0.06
0.19
0.29
0.25
16
ONSCExp149-4D
0.08
0.15
0.1
0.36
0.51
0.46
10.8

Throughout this experiment, an insufficient amount of amine was used compared to aldehyde. This is mostly a result of the inaccuracy of the micropipette used.
Since in a Ugi reaction aldehyde and amine are used in an equimolar amount, results from this experiment may not used to assess the solubility of the Ugi product during the reaction.
[Keeping this error in mind it would still be useful to plot from 0M to 0.46M (total amine components) JCB]

Conclusion

This experiment needs to be redone using a well calibrated micropipettor, or all volume measurements must be avoided in favor of gravimetric measurements.

Log

2009-11-13
11:50 Took out 4 one dram vials. Label 1-2-3-4. Put exactly 21mg phenanthrene-9-carbaldehyde into vial 1, 42mg phenanthrene-9-carbaldehyde into vial 2, 63mg phenanthrene-9-carbaldehyde into vial 3, 105mg phenanthrene-9-carbaldehyde into vial 4.
12:05 Calibrated the 1000uL micropipette and 100uL micropipette. However, calibrating test for 1000uL micropipette failed while for 100uL micropipette is good. Thus, 1000uL micropipette was not used. Instead, masses of benzene were calculated:
To make :
0.1M solution by 21mg phenanthrene-9-carbaldehyde + benzene (843mg) + fufurylamine (9uL) vial 1
0.2M solution by 42mg phenanthrene-9-carbaldehyde + benzene (812mg) + fufurylamine (18uL) vial 2
0.3M solution by 63mg phenanthrene-9-carbaldehyde + benzene (781mg) + fufurylamine (27uL) vial 3
0.5M solution by105mg phenanthrene-9-carbaldehyde + benzene (719mg) + fufurylamine (45uL) vial 4
12:50 Put an amount of fufurylamine into each vial respectively as above.
13:10 Then used the balance to put an amount of benzene into each vial respectively as above.
13:15 Parafilmed all vials to prevent evaporation of benzene.
15:05 Took out four half dram vials. Labeled Exp149-1, Exp149-2, Exp149 - 3, Exp149-4.
15:08 Put a small amount of UCExp176C into each vial. Put approximately 500uL of solution 1,2,3,and 4 into Exp 149 -1, Exp 149 - 2, Exp 149 - 3, Exp 149 - 4 respectively.
15:30 Parafilmed all half dram vials
15:40 Put all half dram vials into the Lauda heating/cooling bath. The temperature is 40C
16:12 Adjusted temperature to 25C
16:35 The temperature in the bath reached 25C.
20:00 Removed the samples from temperature bath and centrifuged the samples.
20:30 Carefully pipetted-out approximately 400uL of the supernatant from each vial and transferred then in to one dram vial containing 300uL DMSO-d6. The one dram vials were labeled ONSCExp149-1D, ONSCExp149-2D, ONSCExp149-3D, ONSCExp149-4D.