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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58 views

Does cinnabar react with iodine?

Does cinnabar react with bromine and iodine to form elemental sulphur? This reaction was described in "Explorations in the history of science and technology in China" but I have doubts...
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phenolsulphonic acid

Phenolsulfonic Acid( PSA) is produced after sulphonation of Phenol at around 100 degrees. They use this product in tinplating. Once a stable PSA is formed after sufficient reaction , unreacted ...
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Will a titanium piercing tarnish if submerged in sulfur water (hot spring)?

I have tried to research whether titanium piercings will tarnish if one submerges in sulfur hot springs. Will titanium piercings react to the sulfur water?
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54 views

What is the density of sodium trimethylsilylpropanesulfonate (DSS)?

I tried to look for the density of sodium trimethylsilylpropanesulfonate (DSS) online but could not find anything. Perhaps someone here measured it/knows where it may be found?
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1answer
90 views

Chemical composition of silver tarnish

I had taken as a given that silver tarnish is a layer of silver sulfide on the surface of a utensil, and that cleaning it using a thiourea based agent like Tarn-X dissolves the sulfide layer. However,...
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2answers
130 views

How to experimentally determine the elemental composition in fingernails?

I am doing a project in my highschool about analysing C/N and C/S ratio of finger nails of various ages and sexes. Please suggest me a way to do this. I don't know where to start, I know the various ...
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1answer
100 views

A question about thiamine [closed]

How does the the nitrogen of thiazole in thiamine acquire a positive charge without being stabilized by another negative charge or by being a salt of an anion?
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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 ($\mathrm{p}K_\mathrm{a}$ ...
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1answer
554 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 ...
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63 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 ...
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1answer
43 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?
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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 ...
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1answer
40 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 ...
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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 ...
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1answer
473 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 $\ce{R3S+}$,...
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1answer
700 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 ...
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1answer
145 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 ...
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1answer
458 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 ...
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1answer
74 views

Is there a single or double bond between S and O in propanethial S-oxide?

I am doing some research on propanethial S-oxide, a chemical produced by onions. I am trying to find out whether they have a single or double bond between the sulfur and oxygen atom. I have seen both ...
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2answers
1k 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?
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57 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?
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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?
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1answer
940 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 ...
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274 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 ...
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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? This ...
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1answer
567 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 ...
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75 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 ...
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107 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. ...
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2answers
1k 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 ...
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1answer
98 views

What can be used to thionate a monosubstituted urea?

I'm looking to make a thiourea from a monosubstituted urea. I haven't found any references that use Lawesson's Reagent, which I have been using for the thionation of di and trisubstituted ureas. Is ...
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360 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:...
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1answer
251 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 ...
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598 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 ...
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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. ...
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1answer
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Which affects acidity more, in relation to induction? (Distance vs. quantity)

I already know that the answer is III. I'm just looking for further explanation on how the others compare to each other, mainly IV vs V. I know that iodine is less electronegative than chlorine, ...
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268 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 ...
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158 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 ...
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1answer
3k 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\ \...
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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 ...
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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 ...
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1answer
271 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 ...
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1answer
81 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, $\...
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1answer
68 views

Can electrostatic interaction affect nucleophilic attack by thiolate anion

Suppose a protein side chain has a $\ce{-SH}$ group which is partially deprotonated to thiolate anion $\ce{-S -}$. This thiolate can perform a nucleophilic attack on a certain substrate. Will the ...
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282 views

Reduction of a disulfide bond

I'm trying to reduce a disulfide bond, I've tried 2-mercapto-ethanol, because I've seen in literature that using a thiol is the most common procedure. I carry out the reaction at 80o C but so far I ...
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1answer
325 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 ...
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1answer
346 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 ...
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436 views

What is the mechanism for the conversion of thiourea to diazomethane?

I really want to know how this reaction works: \begin{align} \ce{SC(NH2)2 + 2 NH3 &-> CH2N2 + 2 NH4+ + S^2-}\\ (\ce{S=C(NH2)2 + 2 NH3 &-> H2C=N=N + S(NH4)2 }) \end{align} This seems ...
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1answer
152 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 ...
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3answers
9k 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 ...
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293 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 ...