Exp056

=media type="custom" key="3135880"= =Objective= To measure the solubility of the [|Ugi product] (206B) in different solvents by NMR. =Procedure= Saturated solutions of ugi product 206B was prepared in seventeen solvents in one dram vials, after vortexing excess solute in each for 10min. The solutions were left to equilibrate over-night. The solutions were then centrifuged and the supernatants were decanted in to separate vials. The supernatants (100uL) were dissolved in a deuterated solvent and an internal standard (10uL) in an NMR tube and a proton NMR was obtained. The relative integrations of a solute peak and the internal standard peak were compared to estimate the concentration of the solute in each supernatant. =Results=

[|Spreadsheet] =Discussion= The Ugi product (206B) is most soluble in Chloroform (0.57M). THF, DMSO, DCM and DMF dissolved the Ugi product to almost same extent (range 0.23- 0.25). Toluene, benzene, carbontet, acetonitrile, ethanol and methanol do not dissovle the Ugi product as well, the extent of its solubility in these solvents range from 0.00- 0.05M. Surprisingly methanol is some what a better solvent than ethanol, It is almost insoluble in water. Cyclohexane, cyclopentane and n-hexane HNMR peaks proved to be coinidental with the t-butyl peaks, the remaining peaks corresponding to the Ugi product were almost absent or insignificant in those solvents, prompting a zero solubility call. The Ugi product is presumed to be less denser than water, DCM, chloroform and carbontet because it floats on these solvents.
 * Solvent || Internal standard || HNMR || Solubility (M) ||
 * THF || Acetone || [|HNMR] || 0.25 ||
 * benzene || Acetonitrile || [|HNMR] || 0.01 ||
 * methanol || Acetonitrile || [|HNMR] || 0.05 ||
 * ethanol || Acetonitrile || [|HNMR] || 0.02 ||
 * toluene || Acetonitrile || [|HNMR] || 0.01 ||
 * acetonitrile || Acetone || [|HNMR] || 0.02 ||
 * chloroform || Acetonitrile || [|HNMR] || 0.57 ||
 * DMSO || Acetonitrile || [|HNMR] || 0.23 ||
 * diethylether || Acetonitrile || [|HNMR] || 0.00 ||
 * cyclohexane || Acetonitrile || [|HNMR] || 0 ||
 * cyclopentane || Acetonitrile || [|HNMR] || 0 ||
 * dichloromethane || Acetonitrile || [|HNMR] || 0.24 ||
 * carbontetrachloride || Acetonitrile || [|HNMR] || 0.00 ||
 * isopropanol || Acetonitrile || [|HNMR] || 0 ||
 * N,N-dimethylformamide || Acetonitrile || [|HNMR] || 0.24 ||
 * water || Acetone || [|HNMR] || 0.00 ||
 * n-hexane || Acetonitrile || [|HNMR] || 0 ||

=Conclusion= Solubility of the Ugi product (206B) has been successfully determined in different solvents. In general the above solvents can be divided in three groups based on the solubility of the Ugi product || cyclopentane, n-hexane, carbontet, acetonitrile, water, diethylether, isopropanol,ethanol and methanol || 0.00-0.05 ||
 * **Solvent** || **Solubility (M)**
 * chloroform || 0.57 ||
 * THF, DMSO, DCM and DMF || 0.23-0.25 ||
 * Toluene, benzene, cyclohexane,

=Log=

2009-02-07
13:00 Prepared satured solutions of the Ugi product (206B) in different solvents listed below. Saturation was achieved by vortexing the solution for 10min after last addition of the solute. (added to the NMR tube) || Int.Std (Peak); Solvent (Peaks) in CDCl3 (ppm) ||
 * Vial number || Solvent || Internal standard
 * 1 || THF || Acetone || 2.16; 3.72 &1.84 ||
 * 2 || benzene || Acetonitrile || 2.00; 7.33 ||
 * 3 || methanol || Acetonitrile || 2.00; 3.66 & 3.43 ||
 * 4 || ethanol || Acetonitrile || 2.00; 3.68, 2.61 & 1.22 ||
 * 5 || toluene || Acetonitrile || 2.00; 7.00-7.38 & 2.34 ||
 * 6 || acetonitrile || Acetone || 2.16; 2.00 ||
 * 7 || chloroform || Acetonitrile || 2.00; 7.25 ||
 * 8 || DMSO || Acetonitrile || 2.00; 2.62 ||
 * 9 || diethylether || Acetonitrile || 2.00; 3.47 & 1.20 ||
 * 10 || cyclohexane || Acetonitrile || 2.00; 1.43 ||
 * 11 || cyclopentane || Acetonitrile || 2.00; 1.50 ||
 * 12 || dichloromethane || Acetonitrile || 2.00; 5.29 ||
 * 13 || carbontetrachloride || Acetonitrile || 2.00; none ||
 * 14 || isopropanol || Acetonitrile || 2.00; 4.00, 2.16 & 1.20 ||
 * 15 || N,N-dimethylformamide || Acetonitrile || 2.00; 8.01, 2.97 & 2.88 ||
 * 16 || water || Acetone || 2.00; 1.58 ||
 * 17 || n-hexane || Acetonitrile || 2.00; 1.29, 1.27 & 0.89 ||

2009-02-08
20:30 The sample were centrifuged, took pics ; [|picture1]; [|picture2] 2:55 The supernatants were decanted into new vials. They were left overnight pending NMR analysis.

2009-02-10
20:00 Obtained HNMR of samples by dissolving 100uL of the saturated solution in a CDCl3 (700uL) except for the water solution for which D2O was used. To all NMR tubes acetonitrile (10uL) was added as an internal standard, except for tubes containing toluene, water and acetonitrile itself, where acetone (10uL) was used as an internal standard.