Researcher

Matthew Federici

Objective


Test the solubility of 4-bromophenylacetic acid, 4-hydroxybenzaldehyde,2,4,6-trimethoxybenzaldehyde, 2,6 dichlorophenylacetic acid,4-nitrobenzaldehyde, 3,4-(methylenedioxy)phenylacetic acid, phenylpropiolic acid, and N-(tert-butoxycarbonyl)-L serine in THF.



Results

SPREADSHEET2
SPREADSHEET





The spectrum for 4-bromophenylacetic acid and THF was not used. The spectra appears to be shifted on the PPM axis and therefore was discarded. There were no results reported for vial H. N-(tert-Butoxycarbonyl)-L Serine and THF did not precipitate any solid. After vial 8 sat on the workbench for 8 days, it was discarded.

All of the other results reported in the SolSum spreadsheet are those that appear in spreadsheet 2. This spreadsheet uses base line correction to increase the accuracy of the results. Spreadsheet 1 does not include baseline correction.

Discussion


There are several different factors in this experiment that effected the results.

Experimentation:
Most of the steps of this experiment were carried out without notable error. During sonication, the lid from vial H fell off. After sonication, Vial H did not precipitate any solid and was discarded. No results were reported for vial H.

The filtration process may have had a significant effect on the recorded molar concentration values. The supernatant began to evaporate in the NMR tubes before the CDCl3 could be added. While the solid was removed with a chem wipe, some of it could have been dissolved when the CDCl3 was added.

NMR Spectra:
The spectra for this experiment are poor. The 500 MHz NMR spectrometer was giving odd results. After significant shimming and relocking, these were the best spectra that could be produced. There is significant shoulders in all of the spectra. There is splitting in some of the spectra as well. The spectra for vial A so too poor even to report results. The quality of the NMR spectra vary from sample to sample. As stated in the log, the 500MHz NMR spectrometer had to be relocked several times and had to be constantly shimmed.

Results:
The spectra for 4-bromophenylacetic acid and THF had an error with the PPM axis. This result was not included in the SolSum spreadsheet. There are no results for N-(tert-Butoxycarbonyl)-L Serine and THF either. Their vial was discarded because the solution sat on the workbench for 8 days and evaporated. Only solid was left in the vial. Therefore, there are no results for this solution in the Solsum spreadsheet.

Conclusion [Add reference section with links to solubility webpages AL]

Molar concentrations were calculated for 6 different solutions. The results significantly differed from other calculated values.

Exp082 result:4-bromophenylacetic acid: 4.79
Exp085 result: 4-bromophenylacetic acid 3.7, 3.73, 3.62
Average of the other experimental values: 3.68
Percent difference with Exp082: 23%


Exp082 result: 4-hydroxybenzaldehyde: 2.44(M)
Exp085 result: 3.91(M)
Exp088 result: 3.72, 3.59, 3.88 (M)
Average of other experimental values: 3.775(M)
Percent difference with Exp082: 55%

Exp082 result: 2, 4, 6-Trimethoxybenzaldehyde: 0.14
No other experiments for 2, 4, 6-Trimethoxybenzaldehyde

Exp082 result: 2,6 Dichlorophenylacetic acid: 3.68
Exp085 result: 2,6 Dichlorophenylacetic acid 2.69, 2.90, 2.86
Average of the other experimental values: 2.82
Percent difference with Exp082: 23%

Exp082 result: 4-Nitrobenzaldehyde: 0.88
Exp000 result: 4-Nitrobenzaldehyde in methanol: 0.50
Exp033 result: 4-Nitrobenzaldehyde in toluene (40C): 0.74
Average of the other experimental values: 0.62
Percent difference with Exp082: 29%

Exp082 result: 3,4-(Methylenedioxy)phenylacetic acid: 2.73
Exp092 result: 4-methoxyphenylacetic acid: 3.56, 3.37, 3.38
Average of the other experimental values: 3.44
Percent difference with Exp082: 26%

Exp082 result: Phenylpropiolic acid: 4.25
Exp085 result: Phenylpropiolic acid: 2.63, 2.47
Average of the other experimental values: 2.55
Percent difference with Exp082: 40%

Weighted difference with Exp082 and comparative values: 36%

Log


4-20-2009

Vial Label
Solute
A
4-Bromophenylacetic acid
B
4-Hydroxybenzaldehyde
C
2,4,6-Trimethoxybenzaldehyde
D
2,6 Dichlorophenylacetic acid
E
4-Nitrobenzaldehyde
F
3,4-(Methylenedioxy)phenylacetic acid
G
Phenylpropiolic acid
H
N-(tert-Butoxycarbonyl)-L Serine


15:25 Labeled 8 half dram from A to H.
15:36 4-Bromophenylacetic acid was added to vial A. 300uL of THF was pippetted into vial A and the solution was vortexed for 30 seconds. After five trials of adding small amounts of 4-Bromophenylacetic acid and vortexing for thirty seconds, the solution appeared to be saturated.
15:41 4-Hydroxybenzaldehyde was added to vial B. 300uL of THF was pippetted into vial B and the solution was vortexed for 30 seconds. After four trials of adding small amounts of 4-Hydroxyaldehyde and vortexing for thirty seconds, the solution appeared to be saturated.
15:44 2,4,6-Trimethoxybenzaldehyde was added to vial C. 300uL of THF was pippetted into vial C and the solution was vortexed for 30 seconds. After two trials of adding small amounts of 2,4,6-Trimethoxybenzaldehyde and vortexing for thirty seconds, the solution appeared to be saturated.
15:49 2,6 Dichlorophenylacetic acid was added to vial D. 300uL of THF was pippetted into vial D and the solution was vortexed for 30 seconds. After four trials of adding small amounts of 2,6 Dichlorophenylacetic acid and vortexing for thirty seconds, the solution appeared to be saturated.
15:52 4-Nitrobenzaldehyde was added to vial E. 300uL of THF was pippetted into vial E and the solution was vortexed for 30 seconds. After two trials of adding small amounts of 4-Nitrobenzaldehyde and vortexing for thirty seconds, the solution appeared to be saturated.
15:54 3,4-(Methylenedioxy)phenylacetic acid was added to vial F. 300uL of THF was pippetted into vial F and the solution was vortexed for 30 seconds. After two trials of adding small amounts of 3,4-(Methylenedioxy)phenylacetic acid and vortexing for thirty seconds, the solution appeared to be saturated.
15:57 Phenylpropiolic acid was added to vial G. 300uL of THF was pippetted into vial G and the solution was vortexed for 30 seconds. After two trials of adding small amounts of Phenylpropiolic acid and vortexing for thirty seconds, the solution appeared to be saturated.
16:04 N-(tert-Butoxycarbonyl)-L Serine was added to vial H. 300uL of THF was pippetted into vial H and the solution was vortexed for 30 seconds. After two trials of adding small amounts of N-(tert-Butoxycarbonyl)-L Serine and vortexing for thirty seconds, the solution appeared to be saturated.
16:07 Vials A to H were placed in a small beaker with some water. This beaker was placed in sonicator at T=26C. The sonicator was turned on and the time was set to thirty minutes.
16:37 The small beaker was taken out of the sonicator. The bath temperature was 40.5C. After sonication, was not solid in vials A, B, G or H. There was solid at the bottom of vials C, D, E, and F. The vials was placed on the workbench and left to sit overnight.

4-21-2009

14:00 Vials A ( contains 4-Bromophenylacetic acid), B (contains 4-Hydroxybenzaldehyde), G (contains Phenylpropiolic acid), and H (contains N-(tert-Butoxycarbonyl)-L Serine) did not form any solid overnight. Therefore, more solute would have to be added to these vials. Vials C (contains 2,4,6-Trimethoxybenzaldehyde), D (contains 2,6 Dichlorophenylacetic acid), E (contains 4-Nitrobenzaldehyde), and F (3,4-(contains Methylenedioxy)phenylacetic acid) had some solid.
14:02: Vials C, D, E, and F were centrifuged.
14:07: Vials C, D, E, and F were taken out of the centrifuge. The solid in these vials condensed to the bottom.
14:10 More solute was added to vials A, B, G, and H and they were vortexed for 30 seconds.
14:15 Vials A, B, G, and H were placed in a small beaker with some water. This beaker was placed in the sonicator. The bath temeperaure was T=24C. The sonicator was turned on.
14:45 The small beaker containing vials A, B, G, and H were taken out of the sonicator. The bath temperature was T=34C. The lid to vial H had fallen off during sonication. Solid still had not formed in any of the vials.
14:47 More solute was added to vials A,B, and G and they were vortexed for 30 seconds.
14:53 Since the lid of vial H had fallen off during sonication, I created a new vial labeled I. N-(tert-Butoxycarbonyl)-L Serine was added to vial I. 300uL of THF was pippetted into vial I and the solution was vortexed for 30 seconds. After three trials of adding small amounts of N-(tert-Butoxycarbonyl)-L Serine and vortexing for thirty seconds, the solution appeared to be saturated. The solution appeared cloudy and solid was forming at the bottom of the vial.
14:58 Vials A, B, G and I were placed in a small beaker with some water. The beaker was placed in the sonicator with a bath temperature of T=27C. The sonicator was turned on and the timer was set for thirty minutes.
15:34 The small taken out of the sonicator. The bath temperature was 36C. Solid had formed in the bottom of vials A,B, and G. Vial H still did not form any solid. These vials were left to sit overnight.

4-23-2009
17:35 NMR tubes were prepared for vials A, B, C, D, E, and F. CDCl3 was used as the deuterated solvent. Vials B, D, and F had to be filtered in order to extract the supernatant. The filtration process is as follows:

1. An empty vial is placed in a test tube rack.
2. A small piece of cotton is placed in a pasteur pipette (pipette A).
3. The pasteur pippette is placed in the test tube rack so the end of the pipett exits into the empty vial.
4. Solution is extracted from one of the test vials (vials A, B, C, D, E, or F) using another pasteur pipette (pipette B).
5. The solution in pippette B is transferred to pippette A. The cotton in pipette A stops the solution from pouring into the empty vial.
6. A rubber bulb is placed on top of pippette A.
7. The rubber bulb is squeezed. This increase in pressure forces the solution through the cotton and into the empty vial. Any solid in the solution gets stuck in the cotton.
8. The filtered solution in the vial is pipetted into an NMR tube.
9. CDCl3 is added to the NMR tube.
10. The NMR tube is capped and labeled.

Some of the supernatant evaporated before CDCl3 could be added into the NMR tubes. This resulted in some solid forming at the top of the NMR tube. This solid was wiped out of the NMR tube using a chem wipe.
17:51 Vial G was filtered and the supernatant was extracted. A NMR tube was prepared for vial G. CDCl3 was used as the deuterated solvent. The solution from vial G had to be shaken with CDCl3 to create a uniform mixture.

4-24-2009
10:40 After adding more solute to vial H, it was placed in the sonicator with bath temperature T=19C.
11:09 Vial H was taken out of the sonicator with bath temperature T=34C. Still, there was not solid.
14:32 THe NMR tubes were tested. Tubes A and B displayed reasonable results on the 500MHz NMR. However, poor results were displayed for tube C.
15:03 Tube C was tested on the 300 MHz NMR. The results were still poor.
15:47 Tubes C, D, E, F, and G were tested on the 500 MHz NMR. The results are displayed above.

4-28-2009
17:52 Vial H was discarded since no solid had formed in 8 days.

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