This tag shall be applied to questions related to organosulfur compounds, i.e. organic compounds that contain sulfur.

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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 ...
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1answer
58 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 ...
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0answers
18 views

Emulsifying Thiols

I've got a chemical solution with a lot of Thiols in it. The Thiol compound(s) keeps on coagulating to the bottom half of the solution. I'd like it more to be dispersed and emulsified. What can I ...
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0answers
18 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 ...
3
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1answer
62 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
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1answer
97 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
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2answers
119 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
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1answer
94 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?
6
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1answer
400 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 ...
6
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1answer
159 views

Which functional group is -CSSH?

If we replace two oxygen in $\ce{-COOH}$ what is the name of the compound we get?
3
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1answer
622 views

What is the effect of substituting oxygen with sulfur in drug molecules?

What sort of changes in the properties of organic or drug molecules can be anticipated if you substitute some or all of the oxygen atoms with sulphur atoms, and vice versa. My interest in this ...
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1answer
637 views

Oxidative chlorination mechanism (sulfide to sulfonyl chloride)

I cannot find much guidance in the literature. Any ideas as to what the mechanism of this reaction might be?
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1answer
1k views

Why do thiols have such a propensity for bonding with mercury?

Historically, thiols $\ce{-SH}$ were known as "mercapto-" due to their strong propensity to bond with mercury. Certain drugs still carry this designation, though mercaptopurine has an $\ce{=S}$ group ...
15
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2answers
204 views

What is a good method to measure the redox potential of a cellular system?

I know how to measure the concentration of free thiols which is reflective of the redox potential of cellular compartment such as the cytoplasm or a lysosome. What other methods exist?