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list of experiments
Solubility book (3rd Edn)
To determine the solubility of Ugi product (
) in methanol, ethanol, acetonitrile, THF, toluene, and DMSO.
Saturated solutions of Ugi product were prepared in methanol, ethanol, acetonitrile, THF, toluene, and DMSO. Six half dram vials were labeled A to F. Ugi product crystals were placed in each of these vials. Methanol was added to vial A, ethanol was added to vial B, acetonitrile was added to vial C, THF was added to vial D, toluene was added to vial E, and DMSO was added to vial F. All of these vials were vortexed for 30 seconds to a minute. Extra Ugi product crystals were added to vials D and F. All of these vials were placed in a small beaker. Vial O from Experiment 77 was also placed in this beaker. Some water was added to the beaker and it was placed in a sonicator for 30 minutes.
Six NMR tubes were labeled A to F in preparation for NMR testing while the vials were in the sonicator. 700uL of Chloroform D was added to all of these NMR tubes. After sonicating for 30 minutes, 100uL of supernatant from vials A, B, C, and E were easily removed using a simple decanting process. These supernatants were placed in their complementary NMR tubes. Supernatant from vials D and F could not be removed by decantation. Both of these vials were centrifuged for 10 minutes. After centrifusion, supernatant from these two vials were removed and placed into their complementary NMR tubes.
These NMR tubes were tested and their results are displayed below.
The 500MHz NMR spectrometer was used to produce these spectra. The spectrometer had to be shimmed a lot and relocked several times. After a number of spectra were generated, the best spectra are displatyed in the results section. Spectra for D, E, and F are especially poor. The solute and solvent peaks have significant shoulders, thus distorting integration. The peaks in
showed odd splitting. The error in this data stems from poor spectra.
The molar concentrations for Ugi product and solvents used in this experiment are low. The highest molar concentration was produced using THF. This value was .49. All other molar concentration values ranged from .04 to .18. The molar concentration values are entered under Ugi product 150D in the Solubility Spreadsheet.
16:30 Labeled 6 half-dram vials from A to F.
16:35 Placed a small amount of the solute (UC216-9A) in each vial
16:40 Pipetted out 300uL of the six primary solvents in to the vials...methanol Vial A, ethanol -Vial B, acetonitrile -vial C, THF- vial D,toluene-vial E and DMSO-vial F.
16:45 Vortexed all vials
16:55 Placed all vials in the sonicator in a small beaker with some water: The vial from Exp 077 was added. The temperature of the beaker was 23C.
17:05 During sonication, the lid from vial A fell off. It was replaced by a new labeled vial.
17:25 All the vials were taken out of the sonicator. The temperature of the beaker was 34C.
17:45 700 uL of CDCl3 were pipetted into a dry NMR tubes labeled A to F. 100 uL of supernantant was removed from vials A, B, C, and E through decantation and placed into their respective NMR tubes. No centrifuging or filtering was required for vials A, B, C, and E. However, vials D and F were centrifuged. After centrifuging, the supernatant from vials D and F was easily pippetted out and placed in their respective NMR tubes. NMR tubes A to F were left to sit overnight.
20:30 NMR tubes A,B,C, aned D were tested using the NMR. Results were recorded for tubes A, B, and C but tube D did not give accurate results. Results from A, B, and C are displayed in the results section.
19:45 NMR tubes D, E, and F were tested using the NMR. There were shimming problems with the NMR and the test results were poor. However, they are displayed in the results section.
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