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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15
votes
4answers
23k views

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
1answer
2k views

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 ...
4
votes
1answer
732 views

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 ...
4
votes
1answer
999 views

Silver-promoted reaction of alkyl halide with diphenyl sulfide

What is the major product formed when 1-chloro-3-iodopropane reacts with diphenyl sulfide in the presence of one equivalent of $\ce{AgBF4}$? I know that sulfur is nucleophilic and that it can ...
6
votes
1answer
343 views

Which functional group is -CSSH?

If we replace two oxygen in $\ce{-COOH}$ what is the name of the compound we get?
3
votes
1answer
2k views

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

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 sulfur atoms, and vice versa. My interest in this ...
10
votes
1answer
1k 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?
21
votes
1answer
4k 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 ...
22
votes
2answers
314 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 lysosomes. What other methods exist?