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.
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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
1
answer
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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
vote
0
answers
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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
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1
answer
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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 ...
12
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3
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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
0
answers
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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
1
answer
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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
1
answer
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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 ...
3
votes
2
answers
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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
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1
answer
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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?
11
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2
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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 ...
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1
answer
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Reliable data describing acidity of 2,4,6-trinitrobenzenesulfonic acid
I wonder what is the $\mathrm{p}K_\mathrm{a}$ or the value of Hammett's $H_0$ function of 2,4,6-trinitrobenzenesulfonic acid? PubChem gives $\mathrm{p}K_\mathrm{a} = 0.13,$ but doesn't specify the ...
17
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4
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Why is pyridine used when making tosyl esters from alcohols?
Tosyl chloride is used to make a hydroxyl group into a better leaving group. However, when the reaction of tosyl chloride and an alcohol occurs, a weak base such as pyridine should be used. Why?
1
vote
1
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How does sulbutiamine work in the same way as thiamine, even if it doesn't have a thiazole ring?
So sulbutiamine is said to be a thiamine substitute.
Yet - it doesn't contain the thiazole ring that's so important for many of thiamine's functions (highlighted in red).
How does it function as a ...
5
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1
answer
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Is there any replacement for ethyl mercaptan in LPG?
Ethanethiol, commonly known as ethyl mercaptan, is a colorless gas added to LPG in order to detect its leakage.
Apart from ethyl mercaptan, is there any gas or liquid that may be used as a ...