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10 votes
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By what mechanism do acids deprotect primary silyl ethers?

Fluoride-mediated deprotection of silyl ethers proceeds through a pentavalent silicon pathway:[1] This mechanism proceeds the same for both primary and secondary silyl ethers, and there's no reason ...
ringo's user avatar
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10 votes
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Why is trimethylsilanol a stronger acid than tert-butanol?

The involvement of d-orbitals in the stabilisation of silanol anions is minimal. The ions $\ce{H3CO-}$ and $\ce{H3SiO-}$ were investigated by Hopkinson and Lien,1 who concluded that: Silicon is a ...
orthocresol's user avatar
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8 votes
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What is nowadays called silazane?

It seems this name should not be in the blue book. It is an error. The following instruction is what Corrections to Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 ...
Mathew Mahindaratne's user avatar
6 votes
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Competitive 'Wittig' vs 'Peterson' C=C bond formation

Seems like the silicon atom is more oxophilic as compared to the phosphorus atom. This could in principal be explained by the higher strength of the $\ce{Si-O}$ bond, as indicated by the dissociation ...
logical x 2's user avatar
  • 2,794
6 votes

Removal of tetrabutylammonium from an organic reaction

I know it is a relative old issue but I had the same problem with nucleosides during my PhD. I tried a wide range of reagents but all of them lead to the decomposition of compounds or no reaction ...
Guillermo Bañuelos Sanchez's user avatar
6 votes

Nomenclature of tertiary amine derivative

The suggested name “1,2-dimethylacetamide-3-propyltrimethoxysilane amine” is not correct for multiple reasons. What are the locants 1, 2, and 3 referring to? There is only one “dimethylacetamide” in ...
Loong's user avatar
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4 votes
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Why is R₃P=O common but R₂Si=O rare?

$\ce{R₂Si=O}$ are referred to as silanone and are extremely reactive. There is an explanation of this in the Wikipedia article: Silanones are extremely reactive and until 2013 were only detected by ...
Nilay Ghosh's user avatar
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4 votes
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What would the mechanism be for intermediate B to Supinidine, and what would by product C be?

The first eq. of MeLi deprotonates the alcohol. This does not cyclise as it would form a 7-membered ring and that is not strongly favoured. The subsequent eqs of MeLi remove the methyl carbamate group ...
Waylander's user avatar
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4 votes
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White growth on unopened bottle of chlorotrimethylsilane

Chlorotrimethylsilane, like other organosilicon compounds, is easily attacked by nucleophiles and readily hydrolyzes in air yielding hydrogen chloride: $$\ce{2 Me3SiCl(l) + H2O(l) -> Me3Si-O-SiMe3(...
andselisk's user avatar
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4 votes

Stabilisation of anions by silicon

3rd period heteroatoms can stabilize adjacent carbanions charges via hyperconjugation (this is sometimes called negative hyperconjugation). Consider ylides used for Corey,-Chaykovsky, Peterson, and ...
Zhe's user avatar
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4 votes

Why are silyl chlorides more readily hydrolysed than alkyl chlorides?

Using $\ce{CCl4}$ and $\ce{SiCl4}$ as the basis for comparison, there are several reasons. The greater electronegativity difference between Si and Cl leads to a larger $\delta^+$ on silicon, making ...
orthocresol's user avatar
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4 votes

What is the density of sodium trimethylsilylpropanesulfonate (DSS)?

The reported crystallographic density for sodium 3-(trimethylsilyl)-1-propane-sulfonic acid monohydrate is $\pu{1.32 g cm^-3}$ [1]. The title compound which is used as reference for some NMR spectra ...
andselisk's user avatar
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3 votes
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Does "silica colloidal anhydrous" contain aluminium?

It will probably have some aluminium in it, likely to be less than 0.1%, and most probably less than 0.01%. Not only that, also expect Ti and Zr in those quantities. This level of impurities does not ...
Gimelist's user avatar
  • 5,430
3 votes

Can Silicon be used as anode for Li-Ion batteries

Generally, heavier atoms means lower specific stored charge per mass. Specific energy per mass depends of the cell redox systems, but also on the above. Silicium, in contrary to carbon, does not ...
Poutnik's user avatar
  • 42.3k
3 votes

Removal of tetrabutylammonium from an organic reaction

I have the same problem in my Ph.D. research. Whenever I am too lazy to skip the aqueous workup and throw the solid residue from rotavapor directly into a column for chromatography, TBA just penetrate ...
Coconut's user avatar
  • 2,108
3 votes

Is there a silicon equivalent to a carboxylic acid?

Acids with a functional group $\ce{Si(O)OH}$ can indeed be formed. One such example is given by Xiong et al.1, illustrated in the abstract as compound 4 in the graphical picture below: As can be seen ...
Oscar Lanzi's user avatar
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2 votes

Competitive 'Wittig' vs 'Peterson' C=C bond formation

You're looking for the faster rate, so given that a triphenylphosphonium (ever see a model of one of these things?) is a lot bulkier than a trimethylsilyl group, I would argue that the sterics is the ...
Zhe's user avatar
  • 17.5k
2 votes
Accepted

Stabilisation of anions by silicon

Since Si is electropositive it should actively destabilise the anion The statement above is largely one based on an inductive effect through the sigma system, in which the polarisation of the C–Si ...
NotEvans.'s user avatar
  • 17.2k
2 votes
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How is silicic acid formed?

As this video clearly confirms, the hydrolysis of SiCl4 is highly exothermic from breaking of chlorine bonds. The solution boils and solid insoluble Si(OH)4 is produced. Also, per Wikipedia on the ...
AJKOER's user avatar
  • 5,556
1 vote
Accepted

Does Sugru (Formerol) decay underwater?

First, the silicone monomer does hydrolyze in water, causing crosslinking. However, the resultant crosslinked polymer is stable. Second, silicone is, one might say, rabidly hydrophobic. For water to ...
DrMoishe Pippik's user avatar
1 vote

How long can a silicone and white spirit solution be stored without hardening?

"White Spirit" or naphtha will dissolve silicone oils. Water will not. Therein lies the secret of using silicone as a water proofing agent. It is applied, much like paint, and the solvent ...
Robert DiGiovanni's user avatar
1 vote

Data on Vapour Pressures of Silicone Oils

Since each manufacturer uses a proprietary mix of silicones, there is no general rule. You'll need to rely on manufacturer's data. Some companies do give actual vapor pressure at specific temperatures,...
DrMoishe Pippik's user avatar
1 vote

Can Silicon be used as anode for Li-Ion batteries

Pure silicon is not conducting like metals. It is an electrical insulator. But it becomes a semi-conductor if it is doped. And it is doped if a tiny amount (less than 1%) of some impurities is present ...
Maurice's user avatar
  • 28.6k
1 vote

how to manufacture PTC ink

It would have been helpful if you have said what kind of polymer-based nanocomposites you would like to create. Yet, I found a good article for the fabrication of poly dimethylsiloxane/carbon ...
Mathew Mahindaratne's user avatar
1 vote

Is the reaction of SiC and H2O a redox reaction?

Silicon carbide is very inert chemically, so this is more of a terminology discussion than discussion of a chemical mechanism. There are two ways of describing the reaction: 1) water oxygenates the ...
James Gaidis's user avatar
1 vote

Decrease in Surface area leads to Increase in load capacity for mesoporous material?

Although I only have access to the abstract of the link you provided (unless you want to spot me $40 ;) they have characterized their glutaraldehyde-functionalized SBA-15 surface using at least 7 ...
airhuff's user avatar
  • 17.5k

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