Objective

To measure the solubility of the phenanthrene-9-carboxaldehyde in different solvents by NMR.

Procedure

Saturated solutions of phenanthrene-9-carboxaldehyde 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
Spreadsheet-060B(this sheet uses SAMS but uses NMRs taken one week after sample preparation)
Spreadsheet-060C (this sheet uses SAMS with the sample prepared the previous day) -[NOTE -only first value for THF currently corrected JCB]

Conclusion

The solubility of phenanthrene-9-carboxaldehyde has been determined in different solvents.

Log

2009-02-15

15:00 Labeled sixteen one dram vials with sixteen solvents listed in the above results table.
15:20 To labeled vials respective solvents (~600uL) was added.
17:00 Three to four narrow spatula full phenanthrene-9-carboxaldehyde was added to each vial, after the addition every vial was vortexed for about 30sec. Vials labeled THF, DMSO and DMF got clear hence another 3 spatula full aldehyde was added to them and vortxed again for 30s. Now all the vials had some undissolved solid remaining in them.
17:40 At this time vials were vortexed for 10 min in groups of 8 tied with rubber band, so it became easier to vortex and also to reduced the over all vortexing time.
18:30 After the vortexing was complete there was still some solid that remained undissolved in each vial. The solutions were then left to equlibrate over night.
21:40 Pictures of the vails containing these solutions were obtained...picture1,picture2

2009-02-16

13:00 Centrifuged all the vials for 3min each. Some of the vials still had the solute dispersed in it..these include dichlormethane. chloroform and carbontet solutions. Cylcohexane, cyclopentane and n-hexane solutions containing vials had solid sticking to the wall of the vials, all over. Obtained a picture of the solutions
14:00 The supernatants from the solution which were clear were decanted in to separate one dram vials. DCM, CHCl3, CCl4 solutions were left undisturbed to fecilitate separation of the supertantat. The aldehyde appeared to be floating on the CCl4 and CHCl3.

2009-02-17

12:00 The solutions of DCM, CHCl3 and CCl4 still had not separated the supernatant well, therefore these solutions were filtered using a very small sintered glass funnel. Again the clear saturated superntatnts obtained were collected in to separate one dram vials.
13:00 Sixteen NMR tubes were cleaned and dried. To each NMR tube a deuterated solvent (700uL)was added, followed by an internal standard -10uL (dichloromethane -5.297ppm, expcept for DCM solution where CH3CN was used). After mixing well, 100uL of the supernatnts was added to the NMR tubes,
The NMR samples were prepared based on the table below,

Deuterated solvent
Internal standard
THF
DMSO-d6
DCM
benzene
DMSO-d6
DCM
methanol
DMSO-d6
DCM
ethanol
DMSO-d6
DCM
toluene
DMSO-d6
DCM
acetonitrile
DMSO-d6
DCM
chloroform
CDCl3
DCM
DMSO
DMSO-d6
DCM
diethylether
DMSO-d6
DCM
cyclohexane
CDCl3
DCM
cyclopentane
CDCl3
DCM
dichloromethane
DMSO-d6
acetonitrile
carbontetrachloride
DMSO-d6
DCM
isopropanol
DMSO-d6
DCM
N,N-dimethylformamide
DMSO-d6
DCM
n-hexane
CDCl3
DCM

While making NMR solution it was noticed that Cyclohexane and n-hexane remained immiscible in DMSO-d6, therefore the saturated solutions of cyclohexane, cyclopentane and n-hexane were dissolved in CDCl3 rathar than DMSO-d6..
Also this time methylene chloride as chosen as an internal standard because its HNMR signal, a singlet stays clear of all the peaks both solvent and solute...its two protons are equivalent and appear at 5.297ppm in CDCl3.
23:30 Obtained HNMR of twelve NMR samples, the cycloalkanes, hexane and chloroform solutions will be run on wednesday,,,Most of the time today, I faced difficulty shimming the 300MHz instrument, this is evident from the peak shapes.

2009-02-18

20:00 Obtained HNMR of the remaining samples.

2009-02-20

11:30 Obtained HNMR once again on the 500MHz Varian instrument..this was done because the HNMRs previously obtained on 300MHz machine showed shimming issues and peak distortions...The HNMRs will be compared with the previously obtained ones on the 300MHz Varian instrument. The NMR tubes containing the samples were left capped in the hood.

2009-02-25

22:00 To NMR tubes containing the samples (in deuterated solvents, of which some may have evaporated) 1,2-dichlorethane (10uL) was added, the NMR solution in the tube was thoroughly mixed.

2009-02-26

03:00 HNMR of the samples were obtained, these spectra are labelled with DCE suffuix...there are series # 3 spectra.

Solvent
Internal standard
HNMR (300MHz)
HNMR (500MHz)
Internal Std
HNMR
THF
DCM
HNMR
HNMR
DCE
HNMR
benzene
DCM
HNMR
HNMR
DCE
HNMR
methanol
DCM
HNMR
HNMR
DCE
HNMR
ethanol
DCM
HNMR
HNMR
DCE
HNMR
toluene
DCM
HNMR
HNMR
DCE
HNMR
acetonitrile
DCM
HNMR
HNMR
DCE
HNMR
chloroform
DCM
HNMR
HNMR
DCE
HNMR
DMSO
DCM
HNMR
HNMR
DCE
HNMR
diethylether
DCM
HNMR
HNMR
DCE
HNMR
cyclohexane
DCM
HNMR
HNMR
DCE
HNMR
cyclopentane
DCM
HNMR
HNMR
DCE
HNMR
dichloromethane
acetonitrile
HNMR
HNMR
DCE
HNMR
carbontetrachloride
DCM
HNMR
HNMR
DCE
HNMR
isopropanol
DCM
HNMR
HNMR
DCE
HNMR
N,N-dimethylformamide
DCM
HNMR
HNMR
DCE
HNMR
n-hexane
DCM
HNMR
HNMR
DCE
HNMR