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.
59
questions
-1
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1answer
46 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?
1
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28 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 ($\mathrm{p}K_\mathrm{a}$ ...
0
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1answer
55 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 ...
1
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0answers
60 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 ...
1
vote
1answer
33 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
0answers
74 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 ...
1
vote
1answer
25 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 ...
0
votes
0answers
21 views
Reaction of aqueous mercury(II) chloride with cysteine?
I know that thiols react with mercury (which is why they were originally known as mercaptans). I haven’t been able to determine what this reaction actually is. If I add HgCl$_2$ to a solution ...
13
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2answers
2k 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 ...
9
votes
1answer
446 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 $\ce{R3S+}$,...
2
votes
1answer
223 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 ...
2
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1answer
78 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 ...
2
votes
1answer
332 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 ...
0
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1answer
31 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 ...
4
votes
2answers
629 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?
2
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0answers
50 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?
9
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0answers
53 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?
4
votes
1answer
602 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 ...
1
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0answers
202 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 ...
3
votes
0answers
49 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?
...
4
votes
1answer
388 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 ...
2
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0answers
70 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 ...
6
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0answers
86 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
2answers
939 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
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1answer
88 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
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0answers
287 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:...
5
votes
1answer
201 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 ...
3
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0answers
428 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
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0answers
1k views
Why do heavy metals like mercury and lead have an affinity for sulfur or sulfur compounds?
Many of the heavy metals such as mercury, lead, thallium, cadmium, and arsenic exert toxic effects largely by binding to or otherwise interfering with organic sulfur compounds or groups in the body. ...
0
votes
1answer
842 views
Which affects acidity more, in relation to induction? (Distance vs. quantity)
I already know that the answer is III. I'm just looking for further explanation on how the others compare to each other, mainly IV vs V.
I know that iodine is less electronegative than chlorine, ...
3
votes
2answers
263 views
Toluenesulfonate vs. methylsulfonate
Are there any advantages/disadvantages of using toluenesulfonate instead of methylsulfonate as a leaving group in E2 and SN2 reactions? I know they are both excellent leaving groups but how do they ...
5
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0answers
147 views
How does lansoprazole degrade in acidic conditions (mechanism)? [closed]
Can anybody help me and explain the mechanism of reaction here? And also I was wondering when disulfide bond is made, can molecule dissociate, return to the previous state and make a disulfide bond ...
1
vote
1answer
2k views
Why do DMSO and acetone have such radically different melting temperatures?
DMSO and acetone have almost identical structures, except for us replacing the carbonyl carbon with sulfur to obtain DMSO. DMSO's melting point is $19~\mathrm{^\circ C}$, whereas acetone's is $-95\ \...
12
votes
2answers
829 views
Sulfinate R/S configuration
How to determine the configuration of the attached chiral compound? It can be represented with two Lewis structures, in the one to the left, the =O substituent has the biggest priority, while in the ...
1
vote
1answer
1k views
Mustard gas hydrolysis (at a very high rate)
Explain mustard gas hydrolysis at a very high rate:
$\ce{Cl-CH2-CH2-S-CH2-CH2-Cl}$
I tried searching online but did not find this reaction anywhere. Can someone explain me the steps/mechanism of ...
2
votes
1answer
238 views
Release of sulfur dioxide from odored fuel gases
Often, fuel gases such as butane and natural gas (methane) are mixed with some foul-smelling impurities such as thiols (mercaptans) and hydrogen sulfide. Presumably, anything containing sulfur would ...
1
vote
1answer
79 views
Why might PM2.5 concentration increase or stay the same when SO2 is reduced?
The question is in the title. I've made some research, but in every paper I found the correlation between $\ce{SO2}$ and $\mathrm{PM_{2.5}}$ is described as positive. Thus if $\ce{SO2}$ is reduced, $\...
0
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1answer
63 views
Can electrostatic interaction affect nucleophilic attack by thiolate anion
Suppose a protein side chain has a $\ce{-SH}$ group which is partially deprotonated to thiolate anion $\ce{-S -}$. This thiolate can perform a nucleophilic attack on a certain substrate.
Will the ...
0
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0answers
273 views
Reduction of a disulfide bond
I'm trying to reduce a disulfide bond, I've tried 2-mercapto-ethanol, because I've seen in literature that using a thiol is the most common procedure. I carry out the reaction at 80o C but so far I ...
12
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1answer
294 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 ...
2
votes
1answer
285 views
Dipole and size of a thioether relative to hydrocarbon
I am an enzymologist and I would like to check whether the consensus of how enzymes tell thioethers from hydrocarbons on substrates is a fact or fiction.
So are any of these wrong?
S–π ...
1
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0answers
383 views
What is the mechanism for the conversion of thiourea to diazomethane?
I really want to know how this reaction works:
\begin{align}
\ce{SC(NH2)2 + 2 NH3 &-> CH2N2 + 2 NH4+ + S^2-}\\
(\ce{S=C(NH2)2 + 2 NH3 &-> H2C=N=N + S(NH4)2 })
\end{align}
This seems ...
2
votes
1answer
139 views
Did my teacher specialist about sulfur compounds made an error in part of Ramberg-Bäcklund rearragement mechanism?
I have a lot of troubles with what I circled in red with the big question mark near. I am not speaking about stereochemistry but about conservation of number of hydrogen atoms, and also there is ...
10
votes
3answers
7k 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 ...
2
votes
0answers
270 views
S-N bond IR vibrations
I am working on organosulfur compounds where i have S-N bonding, according to literature it might be having an ir vibration of 1100cm-1, could anyone confirm it with reference. (the complete bonding ...
2
votes
1answer
125 views
How do I convert 4-(Methylthio)benzaldehyde to 4-(thioacetate)benzaldehyde?
Sorry if I have the incorrect name of the final product. I'm trying to acylate the methyl mercaptan substituent to a thioester (thioacetate). I appreciate any help!
3
votes
1answer
173 views
Attachment of disulfide (protected) thiolated oligonucleotide on gold surface
What will happen if I incubate a clean gold surface in un-deprotected
($\ce{oligo-C6-S-SH}$) thiolated oligonucleotide solution instead of deprotected ($\ce{oligo-C6-SH}$) solution. I have read clean ...
2
votes
2answers
2k views
Why is sodium methanethiolate still a better nucleophile than sodium methoxide when the solvent is ethanol
I'm looking at a problem where sodium methanethiolate and sodium methoxide, both in equal amounts, are being reacted with $\ce{CH3I}$ and the solvent is ethanol.
I understand that sodium ...
3
votes
1answer
651 views
In a nucleophilic substitution reaction, does the other atom to which the nucleophile is bonded matter?
For example,
1-bromopropane + $\ce{NaSH ->}$ Propanethiol + $\ce{NaBr}$
vs.
1-bromopropane + $\ce{H2S ->}$ Propanethiol + $\ce{HBr}$
Which is more valid, and why? Or are they equally valid?
8
votes
1answer
5k views
Mozingo reduction mechanism
I have been searching for the mechanism of the Mozingo reduction on Google but I haven't found anything relevant.
Is the mechanism known? If so, what is it; if not, what hypothetical mechanisms can ...
