Questions tagged [organosulfur-compounds]
For questions about organosulfur compounds, i.e. organic compounds that contain sulfur. These include, but are not limited to, thioesters, thioureas, xanthates, thioacetals, sulfoxides, sulfones, sulfolanes, sulfonic acids, sulfinic acids, disulfides.
81
questions
-1
votes
0
answers
25
views
Trouble understanding thiol deprotonation using potassium carbonate [closed]
I am having trouble understanding how potassium carbonate would deprotonate a thiol group into a thiolate all while being in NMP solvent.
4
votes
1
answer
264
views
Identify the more acidic hydrogen in 1-(methylsulfanyl)propane-2-thione
This was a question that was asked in one of my exams, in which we had to confirm if the given order was correct or incorrect. The key says the given order is correct and the professor at my high ...
- 6,801
13
votes
1
answer
526
views
What is the structure of trifluoromethanesulfonic acid in the gas phase?
During an interesting discussion in our group’s seminar, the question arose what actually causes trifluoroacetic acid to be a much better nucleophile than trifluoromethanesulfonic acid. Part of the ...
- 4,606
4
votes
2
answers
897
views
Why does acidity increase going from sulfide to sulfoxide to sulfone?
It is fairly well-known that the acidity of a proton alpha to a sulfide/sulfoxide/sulfone increases in that order. Some pKa values (in DMSO), courtesy of the Evans pKa table:
Traditionally this has ...
1
vote
1
answer
125
views
Why doesn’t the reaction between 3-mercaptopropionic acid and methyl iodide yield a methyl ester? [closed]
Problem
Answer
Question
I don’t understand why 3‐methylthiopropionic acid (X) is the correct answer. Wouldn’t sulfur and carbon have similar electronegativities?
As the consequence, isn’t it more ...
- 38.4k
1
vote
2
answers
116
views
Mechanism of deprotection of enol thioether
I was reading some enolate chemistry from Carruthers textbook and came across the selective alkylation of unsymmetrical ketones. The reaction involves blocking one alpha-position of the ketone using ...
- 22.6k
2
votes
1
answer
562
views
which is more acidic thiols or carboxylic acid?
According to me as the key atoms are different so when the h+ is released and each of them gets a negative charge as sulphur is a bigger atom compared to oxygen charge is more dispersed , hence the ...
- 22.6k
3
votes
1
answer
459
views
How do I make a 6-mercapto-1-hexanol (MCH) aqueous working dilution?
I am using 6-mercapto-1-hexanol (MCH) as part of the immobilization procedure for forming a self-assembled DNA monolayer on a gold surface (see the first figure of this paper for a good visual ...
2
votes
0
answers
102
views
Protecting Thiol group in presence of alcohol
What protecting group can I use that will protect the thiol in the presence of an alcohol? Is there a set of conditions, or a group that I can use that is selective to the thiol over the alcohol?
I am ...
- 21
3
votes
1
answer
281
views
Detection of Nitrogen and Sulfur in Lassaigne's Test
In Lassaigne's test for the detection of nitrogen and/or sulfur in organic compounds, we prepare Lassaigne's extract. In this extract, NaCN is formed if nitrogen is present, and $\ce{Na2S}$ is formed ...
1
vote
0
answers
91
views
Can stainless steel "soap" bars actually work or is it just deceptive marketing?
The Wikipedia — Stainless steel soap article sounds highly skeptical, although it does include a possible mechanism involving the chromium in the stainless steel binding with the sulfur compounds and ...
- 38.4k
4
votes
1
answer
388
views
Absolute configuration of sulfur in phenyl styryl sulfoxide
Provide absolute configuration to sulfur atom.
I know that oxygen atom will get the highest priority by Cahn–Ingold–Prelog rule, but what about the next priority? I believe it should be phenyl, but ...
- 38.4k
12
votes
3
answers
13k
views
Why do tosylation and mesylation of alcohols follow different mechanisms?
Why do the tosylation and mesylation of an alcohol proceed via different mechanisms?
More specifically,
In tosylation, the lone pair of the alcohol attacks the sulfur in TsCl, but why does it not ...
0
votes
0
answers
67
views
Stable thioesters in biological millieu?
It seems that most thioesters are highly reactive in cells and blood due to the high concentration of biological thiols. Are there any derivatives of thioesters that are stabilized at physiological ...
- 60k
0
votes
0
answers
332
views
What are the relevant pK values on HEPES?
HEPES is 2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethane-1-sulfonic acid. I have read (MA Al-Ghobashy, Bull of Faculty of Pharmacy, Cairo University 2014; 52: 71-78) that the sulfonic acid group is ...
- 4,606