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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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Why doesn’t the reaction between 3-mercaptopropionic acid and methyl iodide yield a methyl ester? [closed]

Problem Answer Question I don’t understand why 3‐methylthiopropionic acid (X) is the correct answer. Wouldn’t sulfur and carbon have similar electronegativities? As the consequence, isn’t it more ...
nmrislife's user avatar
1 vote
2 answers
104 views

Mechanism of deprotection of enol thioether

I was reading some enolate chemistry from Carruthers textbook and came across the selective alkylation of unsymmetrical ketones. The reaction involves blocking one alpha-position of the ketone using ...
Cyclopropanol's user avatar
2 votes
1 answer
477 views

which is more acidic thiols or carboxylic acid?

According to me as the key atoms are different so when the h+ is released and each of them gets a negative charge as sulphur is a bigger atom compared to oxygen charge is more dispersed , hence the ...
zecrosis's user avatar
3 votes
1 answer
374 views

How do I make a 6-mercapto-1-hexanol (MCH) aqueous working dilution?

I am using 6-mercapto-1-hexanol (MCH) as part of the immobilization procedure for forming a self-assembled DNA monolayer on a gold surface (see the first figure of this paper for a good visual ...
Rory Majule's user avatar
2 votes
0 answers
92 views

Protecting Thiol group in presence of alcohol

What protecting group can I use that will protect the thiol in the presence of an alcohol? Is there a set of conditions, or a group that I can use that is selective to the thiol over the alcohol? I am ...
Maya H's user avatar
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3 votes
1 answer
267 views

Detection of Nitrogen and Sulfur in Lassaigne's Test

In Lassaigne's test for the detection of nitrogen and/or sulfur in organic compounds, we prepare Lassaigne's extract. In this extract, NaCN is formed if nitrogen is present, and $\ce{Na2S}$ is formed ...
R H's user avatar
  • 39
1 vote
0 answers
87 views

Can stainless steel "soap" bars actually work or is it just deceptive marketing?

The Wikipedia — Stainless steel soap article sounds highly skeptical, although it does include a possible mechanism involving the chromium in the stainless steel binding with the sulfur compounds and ...
Matt's user avatar
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0 answers
59 views

Stable thioesters in biological millieu?

It seems that most thioesters are highly reactive in cells and blood due to the high concentration of biological thiols. Are there any derivatives of thioesters that are stabilized at physiological ...
toodles's user avatar
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0 answers
303 views

What are the relevant pK values on HEPES?

HEPES is 2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethane-1-sulfonic acid. I have read (MA Al-Ghobashy, Bull of Faculty of Pharmacy, Cairo University 2014; 52: 71-78) that the sulfonic acid group is ...
user37217's user avatar
7 votes
1 answer
467 views

Retrosynthesis of (2E)-1-(2,4-dimethylphenyl)-3-(thiophen-2-yl)prop-2-en-1-one

I am struggling to find a way to disconnect this molecule and I am unsure of the order: First, I was thinking of disconnecting the C=C of the α,β-unsaturated carbonyl. Then for the thiophene group ...
Charlotte's user avatar
3 votes
2 answers
135 views

Mechanism of Grignard reaction with 2-(thiiran-2-yl)oxirane

What will be the final major product? The answer is 2-(methoxymethyl)-3-(substituted methyl)thiirane: I think $\ce{R}$ of $\ce{RMgX}$ attacks thiirane ring because negative charge on sulfur is more ...
Arpit Raj Choudhary's user avatar
4 votes
1 answer
364 views

Absolute configuration of sulfur in phenyl styryl sulfoxide

Provide absolute configuration to sulfur atom. I know that oxygen atom will get the highest priority by Cahn–Ingold–Prelog rule, but what about the next priority? I believe it should be phenyl, but ...
Sushant's user avatar
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1 vote
0 answers
49 views

Questions regarding the Newman-Kwart rearrangement

The Newman-Kwart rearrangement is a reaction that converts a phenol to a thiophenol by forming a phenolic thiocarbamate with two alkyl groups (methyl) on the nitrogen. This is acheived by reacting ...
Jack's user avatar
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3 votes
0 answers
160 views

Is sulphonamide group prone to undergo diazotization?

I wonder if it is not a problem that there is another $\ce{-NH2}$ group in the molecule not connected to aromatic ring and if it can get protonated and react with $\ce{HNO2}$ too, in this case the one ...
Bencyklan's user avatar
0 votes
1 answer
212 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...
Andrey's user avatar
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0 answers
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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 ...
ben cooper's user avatar
-3 votes
2 answers
853 views

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?
Lili Rodriguez's user avatar
1 vote
1 answer
112 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?
Don_S's user avatar
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3 votes
1 answer
925 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,...
iad22agp's user avatar
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0 votes
2 answers
173 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 ...
pjmathematician's user avatar
-1 votes
1 answer
259 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?
mohamed's user avatar
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1 vote
0 answers
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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 ($\mathrm{p}K_\mathrm{a}$ ...
Just A Young Artist's user avatar
2 votes
1 answer
1k 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 ...
studious's user avatar
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1 vote
0 answers
96 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 ...
Preet Bhati's user avatar
1 vote
1 answer
256 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?
CharlotteKhan's user avatar
4 votes
0 answers
1k 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 ...
line112's user avatar
  • 91
1 vote
1 answer
84 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 ...
reuns's user avatar
  • 111
14 votes
2 answers
4k 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 ...
Lazik's user avatar
  • 257
11 votes
1 answer
546 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 $\ce{R3S+}$,...
user73910's user avatar
  • 1,264
3 votes
1 answer
2k 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 ...
Durge's user avatar
  • 33
3 votes
1 answer
232 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 ...
himanshu's user avatar
  • 193
2 votes
1 answer
774 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 ...
Hamish's user avatar
  • 23
1 vote
1 answer
406 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 ...
David Liao's user avatar
5 votes
2 answers
2k 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?
Lauren's user avatar
  • 81
2 votes
0 answers
66 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?
Mr X's user avatar
  • 139
10 votes
0 answers
89 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?
iad22agp's user avatar
  • 9,247
4 votes
1 answer
2k 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 ...
user27533's user avatar
3 votes
0 answers
310 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 ...
Sarah jane's user avatar
4 votes
0 answers
104 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? This ...
spectrum's user avatar
  • 351
4 votes
2 answers
881 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 ...
orthocresol's user avatar
  • 71.2k
2 votes
0 answers
85 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 ...
User2341's user avatar
  • 278
6 votes
0 answers
200 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. ...
Tristan Trevissick's user avatar
9 votes
2 answers
2k 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 ...
Confusedbyeverything's user avatar
0 votes
1 answer
149 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 ...
user48660's user avatar
8 votes
0 answers
616 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:...
orthocresol's user avatar
  • 71.2k
6 votes
1 answer
317 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 ...
ChemDude's user avatar
  • 531
3 votes
0 answers
830 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 ...
Meep's user avatar
  • 1,697
4 votes
0 answers
2k 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. ...
amylakin's user avatar
0 votes
1 answer
2k views

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, ...
Rapid99's user avatar
  • 71
3 votes
2 answers
305 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 ...
Johan's user avatar
  • 197