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81
Organic Chemistry Forum / Re: Boronic acid for suzuki-myura coupling
« Last post by rolnor on March 06, 2025, 03:22:53 AM »
If the reaction on the top works, it seems probable that the bottom reaction should work. How do you plan to introduce the boronic substituent?
82
Inorganic Chemistry Forum / Re: Substance values after dissolving
« Last post by Borek on March 06, 2025, 02:54:53 AM »
Taking the density changes into account the procedure based on mixing 81.53 g of KNO3 with 500 mL of water produces 0.94 ppm of NO3- in the final solution.

For 1 ppm you need to dissolve KNO3 in a somewhat lesser amount of water and the fill it up to 500 mL.

Mistaking volume of solvent with the final volume is a very common error.
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Inorganic Chemistry Forum / Re: Substance values after dissolving
« Last post by Hunter2 on March 05, 2025, 06:26:20 PM »
First consider what Borek said.
It change in this way you have larger volume as 0,5 l. Your values are smaller.

Better is to make a solution in this way. Put   81,53 g in an measured flask  and add water until you get 0,5 l otherwise need the specific gravity, if you dissolve the salt in 0,5 l. The volume will then more as 0,5 l.
If you follow so then you have a solution of 500 ml of it.
You calculate the concentration what means 81,53g/0,5 l = 163,06 g/l
This is equal 163,06 mg/ml.
You dissolve 1 ml  in 100 l means 1,63 mg/l
In mol it's  1,63 mg/l / 101 mg/mmol = 0,016 mmol/l
K = 39,1 mg/mmol * 0,016 mmol/l = 0,63 mg/l = 0,63 ppm K
N = 14 mg/mmol * 0,016 mmol/l = 0,22 mg/l = 0,22 ppm N
NO3- 62 mg/mmol * 0,016 mmol/l = 1,00 m/l = 1 ppm NO3-
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Inorganic Chemistry Forum / Re: Substance values after dissolving
« Last post by Samotonaki on March 05, 2025, 04:18:02 PM »
Thank you both for your replies. I eventually found out that I was calculating the wrong values. I was supposed to calculate the NO3 value, not the N value. Doing that brings me to the expected change of 1 ppm and leads me to believe that now I finally have the correct K value. Below I will share the calculation I have now. Basically, the result should be accurate in 2 decimals. @Borek does your explanation then change anything?

1ppm = 1mg/L, thus 1 ppm increase = 100mg/100L

K = 39,1 g/mol
NO3 = 14 + 3*16 = 62 g/mol

Total = 101,1 g/mol

Mass NO3 in powder :rarrow: 62/101,1 = 0,6133 | 81,53 * 0,6133 = 50g = 50000mg
Mass K in powder :rarrow: 39,1/101,1 = 0,387 | 81,53 * 0,387 = 31,54g = 31540mg

Concentration of N in the solution when adding 1 mL to 100L of demineralised water should then make 50000mg/500ml = 100mg/ml = 1ppm. Concentration of K 31540mg/500ml = 63,08mg/ml = 0,63ppm
85
Organic Chemistry Forum / Boronic acid for suzuki-myura coupling
« Last post by dani on March 05, 2025, 09:01:17 AM »
Hi, I found a  synthetic procedure for 3-aryl-coumarin in litterature (see image coumarin formation 1).
I would like to obtain the product in the image coumarin formation 2 through the similar procedure. I would like to introduce a boronic ester group to use the coumarin in a suzuki-miyura couplin with an aryl bromide. The question is, could the boronic ester inhibit the reaction? It is a lewis acid so it could be a catalyst for this reaction , but I am afraid that it could bound to the hydroxy group of the salicyl-aldehyde reagent inhibiting the reaction.
Thank you very much
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Organic Chemistry Forum / BODIPY decomposition after flash chromatography
« Last post by dani on March 05, 2025, 05:57:42 AM »
Hi evreybody, I am synthetisizing two kind of bodipy molecules . In the last step I functionalize with a triethoxysilane (aminoethylt trymethoxy silane or APTES) group the dyes by the following proces (see also the file attached)
 

BODIPY-COOH + APTES + TEA + COMU  :rarrow: BODIPY-CONHCH2CH2Si(OEt)3

The COOH group is linked through an alkyl chain to the meso position of the bodipy.

After the reaction the solvent is removed and the raw material is purified on silica gel by chromatography with petroleumether/AcOEt 50%/50% to 100% AcOEt as eluent.

Simmetric Bodipy (1,3,5,7 methyl 2,6 ethyl substituted     R=Et in the file attached) is an orange solid stable after the purification
Asimettric Bosipy  (1,3,5,7 methyl 2 ethyl substituted   R=H in the file attached)  is not stable and decompose in a dark red brownish insoluble solid the day after the purification and solvent removal. It happens evrey time I try to isolate it. Anyone knows why does this hanppen?

Thank you very much

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I used neat TFA with sodium nitrate to nitrate a thiophene before. Yields were... OK. I think I used 1.5 equiv of sodium nitrate. Might be worth a shot. I heated it to like 50 degrees I think. This was years ago so I do not remember the exact conditions.
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We have been putting this off in order to pursue some other syntheses, but it is time to move forward.  One of my colleagues uses 90%, and he gave us a protocol recently.  That is a good starting point for us to develop conditions.
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Probably worth trying the 90% before screwing around to try to make the 98% yourself. Both are nasty stuff, even in small amounts they spit out NOx smoke in surprising amounts just from being exposed to the air. It lives up to the name "fuming nitric acid" I assure you.
90
Organic Chemistry Forum / Re: Termination step in free radical substitution
« Last post by Hunter2 on March 03, 2025, 12:57:04 PM »
Yes you got it.
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