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.
82 questions
-4
votes
1
answer
77
views
Does sulfuric acid in snow damage fabric?
Had to do an emergency work in deep snow, in results my black cotton clothes were soaked in it. To my basic knowledge “regular” snow may contain not only salts but also sulfuric acid.
Will snow-...
- 1
4
votes
1
answer
52
views
Comparison of experimental and theoretical FAB+-MS spectra of a PdLClDMSO complex
So I have been characterizing some samples through FAB+-MS and found this:
I am pretty sure that the isotope distribution is correct, but I think there are some deviations which could be due to [M]+ ...
4
votes
1
answer
271
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 ...
- 51
1
vote
1
answer
132
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 ...
- 51
1
vote
2
answers
140
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 ...
- 370
2
votes
1
answer
668
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 ...
- 41
3
votes
1
answer
584
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 ...
- 79
2
votes
0
answers
112
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
314
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 ...
- 39
1
vote
0
answers
98
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 ...
- 11
0
votes
0
answers
77
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 ...
- 137
0
votes
0
answers
379
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 ...
- 53
7
votes
1
answer
476
views
Retrosynthesis of (2E)-1-(2,4-dimethylphenyl)-3-(thiophen-2-yl)prop-2-en-1-one
I am struggling to find a way to disconnect this molecule and I am unsure of the order:
First, I was thinking of disconnecting the C=C of the α,β-unsaturated carbonyl. Then for the thiophene group ...
- 73
3
votes
2
answers
145
views
Mechanism of Grignard reaction with 2-(thiiran-2-yl)oxirane
What will be the final major product?
The answer is 2-(methoxymethyl)-3-(substituted methyl)thiirane:
I think $\ce{R}$ of $\ce{RMgX}$ attacks thiirane ring because negative charge on sulfur is more ...
4
votes
1
answer
435
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 ...
- 41
1
vote
0
answers
51
views
Questions regarding the Newman-Kwart rearrangement
The Newman-Kwart rearrangement is a reaction that converts a phenol to a thiophenol by forming a phenolic thiocarbamate with two alkyl groups (methyl) on the nitrogen. This is acheived by reacting ...
- 21
3
votes
0
answers
173
views
Is sulphonamide group prone to undergo diazotization?
I wonder if it is not a problem that there is another $\ce{-NH2}$ group in the molecule not connected to aromatic ring and if it can get protonated and react with $\ce{HNO2}$ too, in this case the one ...
- 31
0
votes
1
answer
224
views
Does cinnabar react with iodine?
Does cinnabar react with bromine and iodine to form elemental sulphur? This reaction was described in "Explorations in the history of science and technology in China" but I have doubts...
- 1
1
vote
0
answers
79
views
phenolsulphonic acid
Phenolsulfonic Acid( PSA) is produced after sulphonation of Phenol at around 100 degrees. They use this product in tinplating.
Once a stable PSA is formed after sufficient reaction , unreacted ...
- 11
-3
votes
2
answers
1k
views
Will a titanium piercing tarnish if submerged in sulfur water (hot spring)?
I have tried to research whether titanium piercings will tarnish if one submerges in sulfur hot springs. Will titanium piercings react to the sulfur water?
1
vote
1
answer
122
views
What is the density of sodium trimethylsilylpropanesulfonate (DSS)?
I tried to look for the density of sodium trimethylsilylpropanesulfonate (DSS) online but could not find anything. Perhaps someone here measured it/knows where it may be found?
- 1,410
3
votes
1
answer
1k
views
Chemical composition of silver tarnish
I had taken as a given that silver tarnish is a layer of silver sulfide on the surface of a utensil, and that cleaning it using a thiourea based agent like Tarn-X dissolves the sulfide layer.
However,...
- 9,402
0
votes
2
answers
182
views
How to experimentally determine the elemental composition in fingernails?
I am doing a project in my highschool about analysing C/N and C/S ratio of finger nails of various ages and sexes.
Please suggest me a way to do this. I don't know where to start, I know the various ...
- 313
-1
votes
1
answer
287
views
A question about thiamine [closed]
How does the the nitrogen of thiazole in thiamine acquire a positive charge without being stabilized by another negative charge or by being a salt of an anion?
- 567
1
vote
0
answers
33
views
Acidity of 2-sulfopropanedioic acid in water
Sulfuric acid is a strong acid ($\mathrm{p}K_\mathrm{a}$ value below that of $\ce{H3O+}$: completely dissociated in water) at its first deprotonation, but is a weak acid ($\mathrm{p}K_\mathrm{a}$ ...
2
votes
1
answer
1k
views
What should be the name of the given compound?
Following compound is named as
(1) 6-Mercaptocyclohex-4-ene-1,3-diol
(2) 1-Mercaptocyclohex-2-ene-4,6-diol
(3) 1-Mercaptocyclohex-5-ene-2,4-diol
(4) 4-Mercaptocyclohex-2-ene-1,5-diol
As per my ...
- 371
1
vote
0
answers
103
views
What should be IUPAC name of given compound (see image)? [closed]
I think the name should be 1-carbamoylpentane-3-sulphonic acid, but the answer sheet mentions it as 2-carbamoylpentane-3-sulphonic acid:
Can anyone please explain why the chain starting with methyl ...
- 179
1
vote
1
answer
340
views
If heavy metals bind to sulfur why isn't sulfur used as a safer way to chelate them? [closed]
I was wondering about sulfur as an alternative life-threatening chelators. Why isn't sulfur used as a chelator if heavy metals have an affinity for it?
4
votes
0
answers
1k
views
Reaction mechanism of thiol to disulfide oxidation under basic conditions?
I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...
- 91
1
vote
1
answer
86
views
Combustion and pyrolysis of sulfides and organosulfurs
Last week there was a huge fire in french chemical factory Lubrizol, we now know the main products that burnt, to simplify the discussion I extracted a few compounds:
isobutyl and isobutene ...
- 111
14
votes
2
answers
4k
views
How to remove stain from pavement after having dropped sulfuric acid on it?
I had this car battery that flipped in my car trunk.
When I got it out of there it spilled some acid on the pavement. It's a sulfuric acid battery. I added some baking soda on it and poured some more ...
- 257
11
votes
1
answer
552
views
Do quaternary sulfur dications exist?
We know that sulfur can form sulfides $\ce{R2S}$, with two substituents bonded to it. The simplest example of this would be hydrogen sulfide.
However, sulfur can also form sulfonium ions $\ce{R3S+}$,...
- 1,274
3
votes
1
answer
2k
views
At what acid concentration does potassium metabisulfite react?
I'm in the process of developing a well preserved food-stuff containing potassium metabisulfite and a number of acids (acetic, ascorbic, malic, tartaric, citric, lactic). Wine-making literature ...
- 33
3
votes
1
answer
247
views
Attack on cyclic intermediate during NGP
I have studied that when an epoxy ring opening takes place in acidic medium, the ring opens in a way that the most stable carbocation forms. This is due to the positive charge on the oxygen, which ...
- 193
2
votes
1
answer
827
views
Can thiols be created using a Grignard reagent?
I'm trying to find information on the synthesis of thiols via Grignard reagents. While looking at the synthesis routes on Wikipedia, it said that a Grignard reagent will react with sulphur to form ...
- 23
1
vote
1
answer
440
views
Is there a single or double bond between S and O in propanethial S-oxide?
I am doing some research on propanethial S-oxide, a chemical produced by onions. I am trying to find out whether they have a single or double bond between the sulfur and oxygen atom. I have seen both ...
- 111
5
votes
2
answers
3k
views
Thiol prefixes for nomenclature
I've seen multiple prefixes for naming thiols: mercapto-, sulfanyl-, and -thio. Is there a rule for when specific ones are used? And are they used for IUPAC and/or common naming?
- 81
2
votes
0
answers
73
views
How do sulphate esters compare to phosphate esters? [closed]
In particular, the energy released from hydrolysis of the -S-O-S- bonds and how stable are they in aqueous solution compared to phosphate esters?
- 139
10
votes
0
answers
96
views
Does the alpha effect apply to third row elements?
Alkylperoxy anions are stronger nucleophiles than alkoxides (the so-called alpha effect), but would an alkyldisulfide anion be a better nucleophile than an alkylthiolate anion?
- 9,402
4
votes
1
answer
2k
views
Difference between tendency of benzene and thiophene to undergo sulfonation
Why does thiophene possess a greater tendency to undergo sulphonation than benzene? I came across this reaction which employs the use of sulphuric acid to separate thiophene from commercially prepared ...
- 95
3
votes
0
answers
311
views
Is methyl phenyl sulfoxide optically active? [duplicate]
I am concerned about the stereogenic centres. But in this compound there is no chiral centres present. Sulphur is $\mathrm{sp^2}$-hybridized, so it cannot be chiral anyway. But I can see there is no ...
- 754
4
votes
0
answers
109
views
Insertion vs epoxide formation
How can it be explained that in the first reaction mentioned below, a 7-membered ring dominates when the leaving group is nitrogen and an epoxide forms when the leaving group is dimethyl sulfide?
This ...
- 351
4
votes
2
answers
928
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 ...
- 71.9k
1
vote
0
answers
90
views
Deposition of elemental sulfur
I want to create a thin film of elemental sulfur. Based on significant searching, I can find that elemental sulfur deposition is a significant problem in oil and gas. However, I cannot find any ...
- 276
6
votes
0
answers
217
views
Using Ethylene Glycol as anti-freeze in a biodigester gas storage system
I am busy building a bio-digester to produce biogas for cooking/water heating in a cold climate.
I am using the 3 IBC tank solution.
Tank 1 is the digester itself.
Tank 2 is the gas storage unit.
...
9
votes
2
answers
2k
views
Why are peroxides unstable but disulfide bridges considered stable? Why are esters stable but thiolesters are unstable?
I can not understand why a peroxide $\ce{R-O-O-R}$ is considered reactive and unstable.
Going down one row on the periodic table, a disulfide bridge ($\ce{R-S-S-R}$) is apparently super stable and ...
0
votes
1
answer
161
views
What can be used to thionate a monosubstituted urea?
I'm looking to make a thiourea from a monosubstituted urea. I haven't found any references that use Lawesson's Reagent, which I have been using for the thionation of di and trisubstituted ureas. Is ...
8
votes
0
answers
669
views
Sulfonyl azides: diazo or azide transfer?
Sulfonyl azides, $\ce{RSO2N3}$, are capable of acting as sources of electrophilic azide ("$\ce{N+3}$"), but are also capable of effecting diazo transfer, as shown in the scheme below, taken from ref 1:...
- 71.9k
6
votes
1
answer
341
views
Removing sulfur in Barton-Kellogg reaction without triphenylphosphine
I'm trying to understand how the sulfur was removed in the following reaction, taken from a paper by Ben Feringa:1
After some research I found out that this is a Barton-Kellogg reaction. Based on ...
- 531
3
votes
0
answers
872
views
How do thiol groups act as reducing agents?
In my biochemistry practicals, we used reducing agents such as beta mercaptoethanol:
and dithiothreitol (DTT)
Both of these have S-H groups, and I am sure that these are involved in the reduction ...
- 1,717