Objective

To ascertain the solubility of Ugi 216-4a in methanol, ethanol, and acetonitrile by NMR spectroscopy.


Procedure

Saturated solutions of Ugi 216-4a were prepared in methanol, ethanol, and acetonitrile. The solutions were prepared by mixing together the solute and 300μL of the solvent into a vial. With each subsequent addition of solute, there were bouts of vortexing. Once the solutions showed an excess of solute, the vials were sonicated, using a Branson 1510 instrument, for 30 minutes; after which the vials were briefly centrifuged. Solutions were then left to equilibrate. 100μL of the supernatants were micropipetted out and then dissolved into NMR tubes containing 900μL of deuterated chloroform (CDCl3) Proton NMR readings of the solutions are obtained with the use of a 300MHz instrument.



Results

Sample
Solvent
Solute
HNMR
HNMR Raw Data
Solubility (M)
1
Methanol
Ugi 216-4a
HNMR
Ugi216-4-methanol.jdx
0.18
2
Ethanol
Ugi 216-4a
HNMR
Ugi216-4-ethanol.jdx
0.07
3
Acetonitrile
Ugi 216-4a
HNMR
Ugi216-4-acetonitrile.jdx
0.13

Spreadsheet




Discussion

The Ugi product went into solution with the solvent with ease, and not much product was required to saturate the solution; which is further reflected in the low solubility concentrations.

Exp097 reproduced the solubility result for this Ugi product in acetonitrile, and the solubilty results correlate greatly.

Conclusion

The solubility of Ugi 216-4a has been determined in methanol, ethanol, and acetonitrile.


Log

(includes Observations)

2009-05-19

15:22 Temperature within the laboratory was observed to be 21°C.
15:27 A solution of the Ugi solute in methanol was made by adding the solute to 300μL of the methanol solvent into a half-dram vial labeled "Exp093-1A". The vial was briefly vortexed in-between additions of the solute, which was done until the solute was observed to collect within the vial.
15:34 A solution of the Ugi solute in ethanol was made by adding the solute to 300μL of the ethanol solvent into a half-dram vial labeled "Exp093-2A". The vial was briefly vor
texed in-between additions of the solute, which was done until the solute was observed to collect within the vial.
15:42 A solution of the Ugi solute in acetonitrile was made by adding the solute to 300μL of the acetonitrile solvent into a half-dram vial labeled "Exp093-3A". The vial was briefly vortexed in-between additions of the solute, which was done until the solute was observed to collect within the vial.
17:55 Temperature withing the laboratory was observed to be 23
°C.
17:57 Temperature within the sonicator was 26°C.
18:04 Sonicated all vials for 30 minutes.
18:34 End temperature within sonicator was 31°C.
18:35 Centrifuged all vials for 5 minutes.
18:41 Left vials to equilibrate.

2009-05-21

16:38 Temperature within the laboratory was observed to be 24°C.
16:41 Added 1000μL of deuterated chloroform to a NMR tube and labeled it "1A".
16:44 Added 100μL of supernatant from the "Exp093-1A" vial to NMR tube "1A" and briefly vortexed.
16:47 Added 1000μL deuterated chloroform to a NMR tube and labeled it "2A".
16:50 Added 100μL of supernatant from the "Exp093-2A" vial to NMR tube "2A" and briefly vortexed.

16:52 Added 1000μL of deuterated chloroform to a NMR tube and labeled it "3A".
16:53 Added 100μL of supernatant from the "Exp093-3A" vial to NMR tube "3A" and briefly vortexed.
16:55 Obtained NMR
spectra using 500MHz Varian instrument.


References


[[http://oru.edu/cccda/sl/solubility/ugidata.php?solute=Ugi Product 216-4A&solvent=methanol|Solubilty of Ugi 216-4a in methanol]] (Solubility data viewer)
[[http://oru.edu/cccda/sl/solubility/ugidata.php?solute=Ugi Product 216-4A&solvent=ethanol|Solubilty of Ugi 216-4a in ethanol]](Solubility data viewer)
[[http://oru.edu/cccda/sl/solubility/ugidata.php?solute=Ugi Product 216-4A&solvent=acetonitrile|Solubilty of Ugi 216-4a in acetonitrile]](Solubility data viewer)

|| Compound || Inchi Key || Inchi || || Ugi 216-4a || [[http://www.google.com/search?q

QTFHBEDSKOMZFW|QTFHBEDSKOMZFW]]-UHFFFAOYAU || InChI=1/C28H40N2O7/c1-17-10-12-19(36-17)15-20(21(31)16-29-26(33)3 ​7-28(5,6)7)24(25(32)30-27(2,3)4)18-11-13-22(34-8)23(14-18)35-9/h1​ 0-14,20,24H,15-16H2,1-9H3,(H,29,33)(H,30,32) || || Methanol || OKKJLVBELUTLKV-UHFFFAOYAX || InChI=1/CH4O/c1-2/h2H,1H3 || || Ethanol || LFQSCWFLJHTTHZ-UHFFFAOYAB || InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3 || || Acetonitrile || WEVYAHXRMPXWCK-UHFFFAOYAJ || InChI=1/C2H3N/c1-2-3/h1H3 ||=