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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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?
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 ...
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?
13
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2answers
2k views

How to remove stain from pavement after having dropped sulfuric acid on it?

I had this car battery that flipped in my car trunk. When I got it out of there it spilled some acid on the pavement. It's a sulfuric acid battery. I added some baking soda on it and poured some more ...
12
votes
2answers
806 views

Sulfinate R/S configuration

How to determine the configuration of the attached chiral compound? It can be represented with two Lewis structures, in the one to the left, the =O substituent has the biggest priority, while in the ...
12
votes
1answer
294 views

What is the structure of trifluoromethanesulfonic acid in the gas phase?

During an interesting discussion in our group’s seminar, the question arose what actually causes trifluoroacetic acid to be a much better nucleophile than trifluoromethanesulfonic acid. Part of the ...
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?
10
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3answers
7k 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 ...
9
votes
1answer
445 views

Do quaternary sulfur dications exist?

We know that sulfur can form sulfides $\ce{R2S}$, with two substituents bonded to it. The simplest example of this would be hydrogen sulfide. However, sulfur can also form sulfonium ions $\ce{R3S+}$,...
9
votes
2answers
913 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 ...
9
votes
0answers
53 views

Does the alpha effect apply to third row elements?

Alkylperoxy anions are stronger nucleophiles than alkoxides (the so-called alpha effect), but would an alkyldisulfide anion be a better nucleophile than an alkylthiolate anion?
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 ...
8
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0answers
273 views

Sulfonyl azides: diazo or azide transfer?

Sulfonyl azides, $\ce{RSO2N3}$, are capable of acting as sources of electrophilic azide ("$\ce{N+3}$"), but are also capable of effecting diazo transfer, as shown in the scheme below, taken from ref 1:...
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?
6
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0answers
82 views

Using Ethylene Glycol as anti-freeze in a biodigester gas storage system

I am busy building a bio-digester to produce biogas for cooking/water heating in a cold climate. I am using the 3 IBC tank solution. Tank 1 is the digester itself. Tank 2 is the gas storage unit. ...
5
votes
1answer
194 views

Removing sulfur in Barton-Kellogg reaction without triphenylphosphine

I'm trying to understand how the sulfur was removed in the following reaction, taken from a paper by Ben Feringa:1 After some research I found out that this is a Barton-Kellogg reaction. Based on ...
5
votes
0answers
141 views

How does lansoprazole degrade in acidic conditions (mechanism)? [closed]

Can anybody help me and explain the mechanism of reaction here? And also I was wondering when disulfide bond is made, can molecule dissociate, return to the previous state and make a disulfide bond ...
4
votes
1answer
998 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 ...
4
votes
2answers
544 views

Thiol prefixes for nomenclature

I've seen multiple prefixes for naming thiols: mercapto-, sulfanyl-, and -thio. Is there a rule for when specific ones are used? And are they used for IUPAC and/or common naming?
4
votes
1answer
561 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 ...
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
370 views

Why does acidity increase going from sulfide to sulfoxide to sulfone?

It is fairly well-known that the acidity of a proton alpha to a sulfide/sulfoxide/sulfone increases in that order. Some pKa values (in DMSO), courtesy of the Evans pKa table: Traditionally this has ...
4
votes
0answers
54 views

Reaction mechanism of thiol to disulfide oxidation under basic conditions?

I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...
3
votes
2answers
262 views

Toluenesulfonate vs. methylsulfonate

Are there any advantages/disadvantages of using toluenesulfonate instead of methylsulfonate as a leaving group in E2 and SN2 reactions? I know they are both excellent leaving groups but how do they ...
3
votes
1answer
638 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?
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 ...
3
votes
1answer
173 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 ...
3
votes
0answers
49 views

Insertion vs epoxide formation

How can it be explained that in the first reaction mentioned below, a 7-membered ring dominates when the leaving group is nitrogen and an epoxide forms when the leaving group is dimethyl sulfide? ...
3
votes
0answers
408 views

How do thiol groups act as reducing agents?

In my biochemistry practicals, we used reducing agents such as beta mercaptoethanol: and dithiothreitol (DTT) Both of these have S-H groups, and I am sure that these are involved in the reduction ...
2
votes
1answer
68 views

Attack on cyclic intermediate during NGP

I have studied that when an epoxy ring opening takes place in acidic medium, the ring opens in a way that the most stable carbocation forms. This is due to the positive charge on the oxygen, which ...
2
votes
1answer
137 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 ...
2
votes
1answer
312 views

Can thiols be created using a Grignard reagent?

I'm trying to find information on the synthesis of thiols via Grignard reagents. While looking at the synthesis routes on Wikipedia, it said that a Grignard reagent will react with sulphur to form ...
2
votes
1answer
125 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!
2
votes
1answer
174 views

At what acid concentration does potassium metabisulfite react?

I'm in the process of developing a well preserved food-stuff containing potassium metabisulfite and a number of acids (acetic, ascorbic, malic, tartaric, citric, lactic). Wine-making literature ...
2
votes
1answer
229 views

Release of sulfur dioxide from odored fuel gases

Often, fuel gases such as butane and natural gas (methane) are mixed with some foul-smelling impurities such as thiols (mercaptans) and hydrogen sulfide. Presumably, anything containing sulfur would ...
2
votes
2answers
2k 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 ...
2
votes
1answer
280 views

Dipole and size of a thioether relative to hydrocarbon

I am an enzymologist and I would like to check whether the consensus of how enzymes tell thioethers from hydrocarbons on substrates is a fact or fiction. So are any of these wrong? S–π ...
2
votes
0answers
50 views

How do sulphate esters compare to phosphate esters? [closed]

In particular, the energy released from hydrolysis of the -S-O-S- bonds and how stable are they in aqueous solution compared to phosphate esters?
2
votes
0answers
69 views

Deposition of elemental sulfur

I want to create a thin film of elemental sulfur. Based on significant searching, I can find that elemental sulfur deposition is a significant problem in oil and gas. However, I cannot find any ...
2
votes
0answers
266 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 ...
1
vote
1answer
1k views

Mustard gas hydrolysis (at a very high rate)

Explain mustard gas hydrolysis at a very high rate: $\ce{Cl-CH2-CH2-S-CH2-CH2-Cl}$ I tried searching online but did not find this reaction anywhere. Can someone explain me the steps/mechanism of ...
1
vote
1answer
2k views

Why do DMSO and acetone have such radically different melting temperatures?

DMSO and acetone have almost identical structures, except for us replacing the carbonyl carbon with sulfur to obtain DMSO. DMSO's melting point is $19~\mathrm{^\circ C}$, whereas acetone's is $-95\ \...
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 ...
1
vote
1answer
29 views

If heavy metals bind to sulfur why isn't sulfur used as a safer way to chelate them? [closed]

I was wondering about sulfur as an alternative life-threatening chelators. Why isn't sulfur used as a chelator if heavy metals have an affinity for it?
1
vote
1answer
79 views

Why might PM2.5 concentration increase or stay the same when SO2 is reduced?

The question is in the title. I've made some research, but in every paper I found the correlation between $\ce{SO2}$ and $\mathrm{PM_{2.5}}$ is described as positive. Thus if $\ce{SO2}$ is reduced, $\...
1
vote
1answer
25 views

Combustion and pyrolysis of sulfides and organosulfurs

Last week there was a huge fire in french chemical factory Lubrizol, we now know the main products that burnt, to simplify the discussion I extracted a few compounds: isobutyl and isobutene ...
1
vote
0answers
25 views

Acidity of 2-sulfopropanedioic acid in water

Sulfuric acid is a strong acid ($\mathrm{p}K_\mathrm{a}$ value below that of $\ce{H3O+}$: completely dissociated in water) at its first deprotonation, but is a weak acid ($\mathrm{p}K_\mathrm{a}$ ...
1
vote
0answers
58 views

What should be IUPAC name of given compound (see image)? [closed]

I think the name should be 1-carbamoylpentane-3-sulphonic acid, but the answer sheet mentions it as 2-carbamoylpentane-3-sulphonic acid: Can anyone please explain why the chain starting with methyl ...
1
vote
0answers
197 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 ...
1
vote
0answers
1k 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. ...