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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.

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 ...
Confusedbyeverything's user avatar
26 votes
1 answer
5k 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 ...
jonsca's user avatar
  • 3,007
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 ...
NK Yu's user avatar
  • 651
11 votes
2 answers
10k 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 ...
Hippalectryon's user avatar
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 ...
user27533's user avatar
4 votes
0 answers
2k 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. ...
amylakin's user avatar
3 votes
0 answers
168 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 ...
Bencyklan's user avatar
3 votes
0 answers
310 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 ...
Sarah jane's user avatar
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 ...
studious's user avatar
  • 371