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Questions tagged [organophosphorus-compounds]

For questions about the synthesis, properties, or reactivities of organic compounds containing phosphorus; or about reactions in which such compounds are used.

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Clean *di* protection of phosphonic acid dichloride with a suitable protection group with clean deprotection

For some time I am struggling with a tricky synthesis problem in my pHD. I think I came closer now, but I still need a link in the chain to make my idea work. The principle goal here is access a free ...
raptorlane's user avatar
2 votes
1 answer
60 views

(Di)chlorination of phosphonic acid ester

What is the best way to do this reaction to form the dichloride as an reactive intermediate when the substituent R is acid sensitive? In the literature the reaction is either performed with PCl5, a ...
raptorlane's user avatar
3 votes
1 answer
106 views

How can Diethyl Methylphosphonate be reduced into Diethyl Methylphosphonite?

I was reading a study on the synthesis of Diethyl Methylphosphonite and it mentioned three ways to make it. The first way they said was costly and complicated. The second way was then explained in the ...
tryingtofindstand02's user avatar
2 votes
0 answers
35 views

Electrophilic fluorination power: selectfluor vs NFSI

I want to fluorinate the methylene hydrogens between an aryl group and a phosponate ester. The reaction is similar (not identical) to this one: For some reason on the literature people are using very ...
raptorlane's user avatar
1 vote
1 answer
55 views

Why is R₃P=O common but R₂Si=O rare? [closed]

I can understand why R₃N=O is 'rare' since for this double bond to form, Nitrogen would have to recruit a d-orbital like phosphorous does (the charge-separated model) but for N the d-orbitals aren't ...
ajk's user avatar
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2 votes
0 answers
37 views

Synthesize pivaloyloxymethyl ester, but with a substrate that is a terrible nucleophile

I want to synthesize an pivaloyloxymethyl ester from a fluorophosphonic acid. The idea is, to make a compound cell permeable that than be cleaved in the cell by enzymes. Apparently, the acid is a very ...
raptorlane's user avatar
4 votes
0 answers
275 views

Exchange of Fluorine to Oxygen for Fluorophosphonic acid by silylating agents or other methods?

[Warning, long post!] Dear all, I am confronted with a seemingly easy transformation. I want to remove a fluorine atom at a fluor phosphonic acid salt. The usual method to achieve this is the basic ...
raptorlane's user avatar
4 votes
0 answers
114 views

Hydrolyse a fluorophosphonic compound / Which protective group strategy can I use for phosphonate esters to access the free acid after a reaction?

I have a synthetic problem in my PhD thesis, in which I synthesize a phosphonate ester. To be more precise, it is a phosphonofluoridic compound. In my specific case, the fluorine attached to the ...
raptorlane's user avatar
3 votes
0 answers
119 views

Hydrolyse Phosphonate diester to free phosphonic acid under relatively mild conditions?

I want to hydrolyse a phosphonic acid diethylester to the corresponding free phosphonic acid. In the literature, it is described, that usually strongly basic or acidic conditions are utilized to ...
raptorlane's user avatar
1 vote
0 answers
45 views

Esterification of phosphonic acid chloride is working with isoprenol but not with prenol

I am performing an esterfication reaction between an activated phosphonic acid (chloride) and a series of alcohols. Until now, I was not able to make the reaction work with prenol, while isoprenol is ...
raptorlane's user avatar
1 vote
0 answers
33 views

Avoid triethylphosphate as a side product during P-C-P coupling reaction with diethylchlorophosphate with LDA

I have a reaction in which I perform a deprotonation of an acidic proton at a phosphate and later do a P-C-P coupling. The coupling partner is diethylchlorophosphate. Deprotonation is performed with ...
raptorlane's user avatar
0 votes
0 answers
87 views

Why do the two layers of a phospholipid bilayer stick together?

Every answer I can find about why phospholipids form a bilayer says the same thing: hydrophilic heads associate with water, hydrophobic tails do not, so they arrange themselves with heads facing ...
Lysanderoth's user avatar
1 vote
0 answers
97 views

What are the compounds that this article refers to?

The linked article studies the effects of a set of organophosphorus compounds on the bioelectrical activity in the digestive system. The OP compounds studied are referred to in the abstract as IMFF, ...
user73910's user avatar
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1 vote
1 answer
192 views

Does protein phosphorylation add a phosphate group, or does it add a phosphoryl group? Wikipedia seems to have conflicting info on it

Does protein phosphorylation add a phosphate group, or does it add a phosphoryl group? Wikipedia seems to have conflicting info on it Wikipedia on Phosphorylation, https://en.wikipedia.org/wiki/...
barlop's user avatar
  • 503
1 vote
1 answer
290 views

Molybdenum assay (phosphorus vs inorganic phosphate)?

Recently, I have been getting blood tests done for phosphorus. I see some laboratories report phosphorus and others report inorganic phosphate. The normal range for phosphorus seems to be about 0.1 ...
Mikkel Rev's user avatar
3 votes
1 answer
133 views

Should cyaphide create similar chemical compounds as cyanide?

The cyaphide anion $\ce{(CP)-}$ should be chemically similar to its nitrogen analogue cyanide. $\ce{(CN-})$ But unlike it's counterpart it readily polymerizes so it has only been found in outer space ...
Bruh Moments's user avatar
1 vote
1 answer
52 views

Do phosphoryl thiocholines, their uncharged analogs, and other organophosphates, interact differently with Acetylcholinesterase?

As asked in the title, would the various salts -such as hydrochloride or methyl iodide- of V-Agents interact any differently with acetylcholinesterase compared to the neutral compound? For instance, ...
user73910's user avatar
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2 votes
0 answers
37 views

Why is Chlormephos highly toxic despite requiring metabolic activation?

According to the book "The Chemistry of Organophosphorus Pesticides", the insecticide Chlormephos (S-(chloromethyl) O,O-diethyl phosphorodithioate) has an oral LD50 in rats of 7 mg/kg. For ...
user73910's user avatar
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6 votes
1 answer
73 views

Does the mechanism of AChE inhibition by Isoparathion depend on chirality?

It is known that the inhibition of acetylcholinesterase by isomalathion can proceed either with diethyl succinate as the leaving group or thiomethyl, depending on the specific stereoisomer of ...
user73910's user avatar
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4 votes
1 answer
167 views

Why are isomers of parathion less active acetylcholinesterase inhibitors than paraoxon?

Parathion itself has been found to be a very weak inhibitor of acetylcholinesterase. It normally requires metabolic activation and the conversion into paraoxon in the body to actually start exhibiting ...
user73910's user avatar
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6 votes
1 answer
69 views

Naming phosphonium cations in ionic liquids

In Rennie et al., J. Phys. Chem. Lett., 2013, the following cation and anion structures are given in Figure 1. Figure 1(f) is captioned as butyltrimethylphosphonium, which seems to match the given ...
Andrew's user avatar
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2 votes
0 answers
1k views

Purification of Red Phosphorus

The Boring Stuff I'm well acquainted with various fields of science & engineering, but my foray into the world of chemistry is relatively recent. I'm in a location (probably most of us are to some ...
voices's user avatar
  • 159
2 votes
0 answers
38 views

Isomerization of phosphorylated 2-imino-1,3-dioxalanes into phosphorylated cyclic carbamates

I found a patent dating back to the Soviet Union. The patent number is 256764, and the patent describes the synthesis of phosphorylated cyclic carbamates. Here is a section of the patent, followed by ...
user73910's user avatar
  • 1,264
2 votes
1 answer
206 views

Why is methyl parathion less toxic than ethyl parathion?

According to the PubChem pages on ethyl parathion and methyl parathion (pages 11 and 12 of the toxicity section, respectively), methyl parathion is significantly less toxic than ethyl parathion. The ...
user73910's user avatar
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3 votes
1 answer
106 views

Can aged acetylcholinesterase be reactivated?

it is a well-known fact that certain phosphorus compounds can inhibit the enzyme acetylcholinesterase, and that the treatment of poisoning with such compounds is administration of atropine and some ...
user73910's user avatar
  • 1,264
2 votes
0 answers
417 views

Differences in Novichok agent mass spectra

As we have all heard, in 2018, a series of poisonings with a nerve agent alleged to be of the Novichok series was carried out on British soil. It is claimed that the agent used was A-234. However, a ...
user73910's user avatar
  • 1,264
6 votes
2 answers
862 views

Reagent choice in the formation of Wittig reagent

During the formation of Wittig reagent, BuLi is used as it is a VERY strong base (pKa = 50). According to Wikipedia, however, sulfur ylide is 'especially conveniently' made from dimsyl anion (pKa = 35)...
234ff's user avatar
  • 549
0 votes
1 answer
419 views

What is the true caloric impact of Alcohol?

I've only had 1 year of basic Chemistry at school, so I am waay too uneducated to answer this question myself: What is the true caloric impact of ingested alcohol (ethanol) in the human body? Here ...
JayC667's user avatar
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2 votes
0 answers
85 views

Differences in efficacy of oxime reactivators in organophosphate poisoning

Compounds containing an oxime functional group, such as 2-PAM and obidoxime, are used in the treatment of poisoning with organophosphorus compounds. These oximes reactivate the enzyme ...
user73910's user avatar
  • 1,264
10 votes
2 answers
873 views

AChE Aging time of organophosphorus compounds containing hydroxyl groups

Organophosphorus compounds are known to inhibit the enzyme acetylcholinesterase (AChE). This occurs when the OPC phosphorylates the serine-203 residue of the enzyme. If the enzyme is not reactivated ...
user73910's user avatar
  • 1,264
1 vote
1 answer
844 views

Triphenylphosphine (PPh3) vs. 1,2-bis(diphenylphosphino)ethane (dppe) ligand?

What about $\ce{NiCl2(dppe)}$ makes it a more efficient catalyst for Suzuki cross-coupling as opposed to $\ce{NiCl2(PPh3)2}$ or $\ce{NiCl2(PCy3)2}$? How does the dppe ligand increase the reactivity of ...
cjperkie's user avatar
5 votes
2 answers
9k views

How to convert P2O5 concentration to H3PO4 concentration?

Why are some elements such as phosphorus reported as $\ce{P2O5}$ concentrations when the materials have no $\ce{P2O5}$ in them. I would like an explanation of how the conversion is done between real ...
dlight's user avatar
  • 337
-7 votes
1 answer
4k views

Is Phosphate (PO4 3-) solube in water? [closed]

Josh~ Superphosphate is used instead of just phosphate because superphosphate is a compound whereas phosphate is an ion. This means that phosphate must attach itself with a cation in order to give a ...
ALBERT NEWTON's user avatar
3 votes
1 answer
676 views

Rationalising the reactivity of phosphoryl chloride

$\ce {POCl3}$ is a reagent well-known for enacting various functions in organic synthesis. For example, together with pyridine, it is able to dehydrate alcohols to give alkenes. Also, reacting it with ...
Tan Yong Boon's user avatar
15 votes
1 answer
8k views

Explanation of the strength of phosphorus–oxygen bond

When discussing the Wittig reaction, Clayden's Organic Chemistry (2nd ed.) cites the strength of the P=O bond formed in triphenylphosphine oxide as a driver of the reaction through enthalpy: The P=...
Ethiopius's user avatar
  • 811
11 votes
1 answer
640 views

Is phosphorine (C₅H₅P) aromatic?

Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is ...
user137644's user avatar
1 vote
1 answer
48 views

What is the configuration of dimethyl[tris(trifluoromethyl)]-λ⁵-phosphane?

I know that $\ce{(CH3)2P(CF3)3}$ is geometry of trigonal bipyramid and according to Bent's rule $\ce{CH3}$ goes to axial positions and $\ce{CF3}$s remains on equatorial positions. However, as per ...
Random guy's user avatar
2 votes
1 answer
165 views

How come one of the hydroxides in the phosphate group are more acidic than the other?

Three phsiologically relevant $\mathrm{p}K_\mathrm{a}$ values are associated with psilocybin: 1.3, 6.5 and 10.4. Suggest the appropriate charged species and mark the $\mathrm{p}K_\mathrm{a}$ values ...
Eli Lawrence's user avatar
2 votes
0 answers
36 views

Phosphonate reaction with oxides and their stability?

I have read some papers stating that $\ce{SiO2}$ surfaces can bind phosphonates, but in water they hydrolyse. However, for $\ce{Si}$ surfaces, they are stable in water. In both cases, the reaction ...
hmm...'s user avatar
  • 101
2 votes
0 answers
69 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
3 votes
1 answer
1k views

Triphenylphosphine vs. trimethylphosphine in reduction reactions

Triphenylphosphine is used typically as a reducing agent for organic peroxides as it is a good nucleophile. So, if I wanted to computationally model a reaction like: $$\ce{PR3 + ROOH -> OPR3 + ROH}$...
t.dot's user avatar
  • 111
2 votes
1 answer
4k views

How are phosphoglycerides different from phospholipids?

(Currently studying high-school Biochemistry) I'm unable to distinguish between phospholipids and phosphoglycerides from their "definitions" (Courtesy: Wikipedia) On phospholipids: Which suggests ...
paracetamol's user avatar
  • 18.8k
-4 votes
1 answer
8k views

What is the difference between metaphosphoric acid and phosphonic acid? [duplicate]

Are metaphosphoric acid and phosphonic acid the same? I have been told that they're same BUT the structures online are different. Metaphosphoric acid has formula: $\ce{(HPO3)_n}$ phosphonic acid ...
lalalalala's user avatar
11 votes
1 answer
5k views

Mechanism of homologation of aldehyde to alkyne: Ohira–Bestmann reaction

This reaction was part of an organic scheme I was doing, and I was wondering what the mechanism of the reaction would be. I tried first forming a carbene by letting $\ce{N2}$ leave from the ...
carbenoid's user avatar
  • 2,042
1 vote
0 answers
60 views

Reaction of phosphonates with conjugated carbonyl compounds

I was wondering whether the phosphonate ion would do a Michael addition on to the double bond rather than attacking the $\ce{C=O}$ bond to form the alkene product as it usually does (e.g. in a Horner–...
Mrityunjay Gupta's user avatar
16 votes
4 answers
15k views

Can ATP be synthesized and consumed?

I do not understand why you could not fill a bowl full of adenosine triphosphate (ATP) and eat it. Is there a way to make ATP other than inside a cell and apply it to your body by injection, ingestion,...
Muze's user avatar
  • 1
6 votes
2 answers
9k views

What is the difference between a phosphoryl group and a phosphate group?

I am looking at covalent modification of enzymes and I found out that only one of these types is phosphorylation. But I do not understand what the difference between the a phosphate and a phosphoryl ...
Viv's user avatar
  • 323
0 votes
1 answer
10k views

difference between glyceraldehyde-3-phosphate and 3-phosphoglycerate

In the photosynthetic dark reaction there are two types of reactions: light-dependent and light-independent. In the light-independent reactions during reduction 3-phosphoglycerate is converted to ...
Esha Mukhopadhyay's user avatar
9 votes
2 answers
669 views

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

If one considers the intermediate above, there are immediately two possibilities for subsequent reaction: 1. A Wittig-type olefination which would lead to a vinyl silane: This reaction happens to be ...
NotEvans.'s user avatar
  • 17.2k
13 votes
1 answer
1k views

Is phosphorus a stereogenic centre in this phosphate ester?

My textbook says that in the above diagram that there is only 2 stereoisomers. I am guessing this is due to the stereogenic carbon atom and not due to the phosphorus atom which apparently isn't a ...
Nanoputian's user avatar
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