Objective

To study the kinetics of a Ugi reaction in benzene by NMR; the Ugi product was first synthesized in UsefulChem Exp176.

Procedure

In to a clean and dry NMR tube weigh phenanthrene-9-carboxaldehyde (0.25mmol, 52mg), pipette out benzene (505uL) in to the tube. [0.46M]. Obtain HNMR. Add furfurylamine (0.25mmol, 22.3uL) to the tube. Obtain HNMR. Add phenylacetic acid (0.25mmol, 34mg) to the tube, sonicate for 10min to dissolve the solid. Obtain HNMR. Wait for 3h, in order to establish an equilibrium. Add n-butylisocyanide (0.25mmol, 26.4uL). Obtain HNMRs every few min, possibly (0, 2, 4, 8, 16, 32, 64, 128, 256, 512min, and as much as possible)
Final Conc Estimation
aldehyde+benzene = 547.73uL
amine = 22.3uL
acid = 29.21uL
isocyanide = 26.4uL
*--------------------*
Total = 625.638uL
Concentration = 0.25/0.625 = 0.403M

Results

Discussion

Conclusion

Log

2009-11-03
19:10 Weighed out phenanthrene-9-carboxaldehyde (0.25mmol, 52mg) in to a clean and dry NMR tube. Pipetted out benzene (505uL) in to the NMR tube. Vortexed the solution (in the tube) until the solid dissolved, the tube had been capped tightly while it was vortexed
19:20 Obtained HNMR of the solution, after placing an NMR coaxial insert containing DMSO-d6 inside the tube containing the solution.
19:39 Pipetted out fufurylamine (0.25mmol, 22.3uL) in to the NMR tube containing the aldehyde solution, the resulting solution is now called UCExp252-1A.
19:44 Obtained HNMR of UCExp252-1A - UCExp252-1A-5min
19:56 Obtained HNMR of UCExp252-1A - UCExp252-1A-17min
20:07 Obtained HNMR of UCExp252-1A - UCExp252-1A-28min
20:23 Obtained HNMR of UCExp252-1A - UCExp252-1A-44min
20:31 Obtained HNMR of UCExp252-1A - UCExp252-1A-52min
20:39 Obtained HNMR of UCExp252-1A - UCExp252-1A-60min
2009-11-04
06:45 Weighed out phenylacetic acid (0.25mmol, 34mg)
07:03 Obtained HNMR of UCExp252-1A - UCExp252-1A-11h24min
07:15 Obtained HNMR - UCExp252-1A-11h36min
07:22 Obtained HNMR - UCExp252-1A-11h43min
07:32 Added phenylacetic acid (34mg) to the tube containing UCExp252-1A, the resulting solution is now labeled UCExp252-2A.
07:36 Obtained HNMR - UCExp252-2A-04min
07:43 Obtained HNMR - UCExp252-2A-11min
07:48 Obtained HNMR - UCExp252-2A-16min
07:59 Obtained HNMR - UCExp252-2A-27min
08:05 Obtained HNMR - UCExp252-2A-33min
08:08 Added n-butylisocyanide (0.25mmol, 26.4uL) to the tube containing UCExp252-2A, the resulting solution is now re-labeled UCExp252-3A.
08:11 Obtained HNMR - UCExp252-3A-03min
08:15 Obtained HNMR - UCExp252-3A-07min
08:18 Obtained HNMR - UCExp252-3A-10min
08:23 Obtained HNMR - UCExp252-3A-15min
08:27 Obtained HNMR - UCExp252-3A-19min
08:34 Obtained HNMR - UCExp252-3A-26min
08:42 Obtained HNMR - UCExp252-3A-34min
08:47 Obtained HNMR - UCExp252-3A-39min
08:55 Obtained HNMR - UCExp252-3A-47min
09:06 Obtained HNMR - UCExp252-3A-58min
09:12 Obtained HNMR - UCExp252-3A-64min
09:22 Obtained HNMR - UCExp252-3A-74min
10:43 Obtained HNMR - UCExp252-3A-2h35min /155min
10:51 Obtained HNMR - UCExp252-3A-2h43min/163min
12:17 Obtained HNMR - UCExp252-3A-4h09min/249min
12:27 Obtained HNMR - UCExp252-3A-4h19min/259min
12:35 Obtained HNMR - UCExp252-3A-4h27min/267min
15:57 Obtained HNMR - UCExp252-3A-7h49min/469min
16:24 Obtained HNMR - UCExp252-3A-8h06min/486min
16:36 Obtained HNMR - UCExp252-3A-8h28min/508min
16:40 Obtained HNMR - UCExp252-3A-8h32min/512min
16:46 Obtained HNMR - UCExp252-3A-8h38min/518min
16:50 Obtained HNMR - UCExp252-3A-8h42min/522min
17:37 Obtained HNMR - UCExp252-3A-9h29min/569min
17:46 Obtained HNMR - UCExp252-3A-9h38min/578min
17:49 Notice very fine crystals developing in the NMR tube.