Exp150

=Researchers= =Objective= To measure the solubility of the Ugi product UC176C in methanol with a) phenanthrene-9-carbaldehyde b) furfurylamine and c) phenylacetic acid as co-solutes at different concentrations. =Procedure= 0C, after 30min change the temp to 25C. Leave the sample in the bath for another 30min to equilibrate. Then centrifuge the sample vial and obtain the supernatant in DMSO-d6. Obtain HNMR of the solution [|Calculations-link] =Results= [|Spreadsheet-link]
 * Hai Truong and Khalid Mirza**
 * 1) To ~1mL methanol in to a half dram vial add the Ugi product 176C; vortex the solution, make sure some of the solute remains undissolved. Place the solution in water/glycol bath at
 * 1) Make-up a 0.053M solution of phenanthrene-9-carboxaldehyde in methanol, by dissolving 0.053mmol, 11mg in a 1mL volumetric flask.
 * 2) Make-up a 0.106M solution of phenanthrene-9-carboxaldehyde in methanol by dissolving 0.106mmol, 22mg in 1mL in a 1mL volumetric flask.
 * 3) Make-up a 0.113M solution of fufurylamine in methanol by dissolving 10uL furfurylamine (1.13mmol) in a 1mL volumetric flask.
 * 4) Make-up a 0.509M solution of furfurylamine in methanol by dissolving 45uL (5.11mmol) in a 1mL volumetric flask.
 * 5) Make-up a 0.870M solution of phenylacetic in methanol by dissolving 474mg (4mmol) in methanol in a 4mL volumetric flask (This is solution **150A**)
 * 6) Dilute solution 150A to obtain 0.0435M, 0.0870M, 0.174M, 0.261M and 0.435M solutions (all ~ 1mL)

=Discussion=

//Table -ONSExp150-i// = = number** || **Solution source** || **co-solute** || **co-solute conc (M)** || **SAMS conc co-solute (M)** || **Ugi Product Solubility (M)** || carboxaldehyde || 0.053 || 0.03 || 0.01 || There is no effect on the solubility the Ugi product UC176C when other co-solutes are present in its solution in methanol.
 * **NMR solution
 * ONSCExp150-1B || Exp150-1 || None || -- || -- || 0.01 ||
 * ONSCExp150-2B || Exp150-2 || None || -- || -- || 0.01 ||
 * ONSCExp150-3B || Flask 01 || phenanthrene-9-
 * ONSCExp150-4B || Flask 03 || furfurylamine || 0.113 || 0.12 || 0.01 ||
 * ONSCExp150-5B || Flask 04 || furfurylamine || 0.509 || 0.43 || 0.01 ||
 * ONSCExp150-6B || Flask 05 || phenylacetic acid || 0.431 || 0.05 || 0.01 ||
 * ONSCExp150-7B || Flask 06 || phenylacetic acid || 0.087 || 0.09 || 0.01 ||
 * ONSCExp150-8B || Flask 07 || phenylacetic acid || 0.174 || 0.19 || 0.01 ||
 * ONSCExp150-9B || Flask 08 || phenylacetic acid || 0.261 || 0.26 || 0.01 ||
 * ONSCExp150-10B || Flask 09 || phenylacetic acid || 0.435 || 0.44 || 0.01 ||
 * [Compare the pure Ugi product solution values with previous values in methanol - does it make sense? These new values also need to be added to the solsum sheet JCB]**

=Conclusion= Solubility of the Ugi product 176C remains unaffected by the type and concentration of co-solutes in methanol up to 0.43M furfurylamine, 0.44M phenylacetic acid or 0.03M phenanthrene-9-carboxaldehyde separately.

=Log=


 * 2009-11-19**
 * 16:05** Took out 2 half dram vials, labeled **Exp-150-1**, **Exp 150-2** and put into each approximately 1000ul methanol. Put small amount of Ugi product 176C into both vial so that there is still small mount of solid Ugi remain in the liquid.- **Blanks**
 * 16:10** Parafilm both of them
 * 16:20** Put them into Lauda heating/cooling bath. The current temperature in the bath was 30C. Adjust it to 40C.
 * 16:40** Temperature in the bath was 40C
 * 17:10** Adjusted temperature in the bath to 25C
 * 17:25** Temperature reached 25C. Let them in the bath for whole night.

For flask **01:** Made-up a **0.053M** solution of phenanthrene-9-carboxaldehyde in methanol, by dissolving 0.053mmol, 11mg in a 1mL volumetric flask. For flask 02:Tried to make-up a 0.106M solution of phenanthrene-9-carboxaldehyde in methanol by dissolving 0.106mmol, 22mg in 1mL in a 1mL volumetric flask.- The solute did not dissolve in the solvent. //Therefore, 0.1M solution of phenanthrene-9-carboxaldehyde in flask 2 is discarded//. For flask **03:** Made-up a **0.113M** solution of fufurylamine in methanol by dissolving 10uL furfurylamine (1.13mmol) in a 1mL volumetric flask. For flask **04:** Made-up a **0.509M** solution of furfurylamine in methanol by dissolving 45uL (5.11mmol) in a 1mL volumetric flask. //In a 4ml volumetric flasks__:__// Made-up a **0.870M** solution of phenylacetic in methanol by dissolving 474mg (4mmol). This is solution- **150A**. For flask **05**: From 150A solution, took 50ul transferred in to a 1mL volumetric flask, **05** and diluted it to 1ml by adding methanol. This is a **0.0431M** phenylacetic acid solution. For flask **06**: From 150A solution, took 100ul transferred in to a 1mL volumetric flask, **06** and diluted to 1ml by adding methanol. This is a **0.0870M** phenylacetic acid solution. For flask **07**: From 150A solution, took 200ul transferred in to a 1mL volumetric flask, **07** and diluted to 1ml by adding methanol. This is a **0.174M** phenylacetic acid solution. For flask **08**: From 150A solution, took 300ul, transferred in to a 1mL volumetric flask, **08** and diluted to 1ml by adding methanol. This is a **0.261M** phenylacetic acid solution. For flask **09**: From 150A solution, took 500ul transferred in to a 1mL volumetric flask, **09** and diluted to 1ml by adding methanol. This is a **0.435M** phenylacetic acid solution. __//Note//__: There was still small amount of solute undissolved in each vial. 13:10 Removed the vials from the temperature control bath. 13:35 Centrifuged the vials. 13:45 Carefully pipetted-out approximately 400uL of the supernatant from each vial and transferred then in to one dram vial containing 300uL DMSO-d6. The one dram vials were labeled **ONSCExp150-1B**, **ONSCExp150-2B,** **ONSCExp150-3B,** **ONSCExp150-4B,** **ONSCExp150-5B,** **ONSCExp150-6B,** **ONSCExp150-7B,** **ONSCExp150-8B,** **ONSCExp150-9B** and **ONSCExp150-10B** 16:50 Completed obtaining HNMRs for each of the ONSCExp150-#B solutions.
 * 2009-11-20**
 * 12:05** Took out nine 1ml-volumetric-flasks and one 4ml volumetric flasks, cleaned with acetone and put into the oven for 5 minutes.
 * 12:13** Took all the flasks out from the oven. Labeled from 1-9 for 1ml volumetric flasks, then:
 * 14:20** Took out 8 half dram vials and labeled: **Exp-150-3, Exp-150-4, Exp-150-5, Exp-150-6, Exp-150-7, Exp-150-8,Exp-150-9, Exp-150-10,** in which:
 * Exp-150-3**: Transferred from flask 01: 500ul of 0.053M solution of phenanthrene-9-carboxaldehyde in methanol and small amount of solute 176C
 * Exp-150-4**: Transferred from flask 03: 500ul of 0.113M solution of fufurylamine in methanol in methanol and small amount of solute 176C
 * Exp-150-5**: Transferred from flask 04: 500ul of 0.509M solution of furfurylamine in methanol and small amount of solute 176C
 * Exp-150-6**: Transferred from flask 05: 500ul of 0.0431M solution of phenylacetic in methanol and small amount of solute 176C
 * Exp-150-7**: Transferred from flask 06: 500ul of 0.0870M solution of phenylacetic in methanol and small amount of solute 176C
 * Exp-150-8**: Transferred from flask 07: 500ul of 0.174M solution of phenylacetic in methanol and small amount of solute 176C
 * Exp-150-9**: Transferred from flask 08: 500ul of 0.261M solution of phenylacetic in methanol and small amount of solute 176C
 * Exp-150-10**: Transferred from flask 09: 500ul of 0.435M solution of phenylacetic in methanol and small amount of solute 176C
 * 15:16** Parafilmed all of the vials.
 * 15:30** Put all vials into Lauda heating/cooling bath. Adjusted temperature to 40C. There were totally 10 vials in the bath: 2 from last night and 8 from today.
 * 16:00** Temperature in the bath was 40C. Lowered temperature to 25C.
 * 16:25** Temperature reached 25C.
 * 2009-11-21**

= =
 * NMR solution number || Solution source || Cosolute Name || Cosolute conc(M) || SAMS conc of cosolute (M) ||
 * ONSCExp150-1B || Exp150-1 || None || -- || -- ||
 * ONSCExp150-2B || Exp150-2 || None || -- || -- ||
 * ONSCExp150-3B || Flask 01 || phenanthrene-9-carboxaldehyde || 0.053 || 0.03 ||
 * ONSCExp150-4B || Flask 03 || furfurylamine || 0.113 || 0.12 ||
 * ONSCExp150-5B || Flask 04 || furfurylamine || 0.509 || 0.43 ||
 * ONSCExp150-6B || Flask 05 || phenylacetic acid || 0.431 || 0.05 ||
 * ONSCExp150-7B || Flask 06 || phenylacetic acid || 0.087 || 0.09 ||
 * ONSCExp150-8B || Flask 07 || phenylacetic acid || 0.174 || 0.19 ||
 * ONSCExp150-9B || Flask 08 || phenylacetic acid || 0.261 || 0.26 ||
 * ONSCExp150-10B || Flask 09 || phenylacetic acid || 0.435 || 0.44 ||