Questions related to organosulfur compounds that contain a carbon-bonded sulfhydryl (–C–SH or R–SH) group (where R represents an alkane, alkene, or other carbon-containing group of atoms).

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2
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2answers
31 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
votes
1answer
32 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
votes
1answer
121 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
414 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 ...
14
votes
1answer
794 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 ...
12
votes
2answers
179 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?