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.

Filter by
Sorted by
Tagged with
3
votes
1answer
713 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 ...
15
votes
4answers
25k 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
784 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
1k 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
377 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
323 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?

1
2