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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90 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 ...
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27 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, ...
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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 ...
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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 ...
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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 ...
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1answer
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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 ...
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230 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 ...
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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 ...
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1answer
129 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 ...
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1answer
66 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 ...
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308 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 ...
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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)...
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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 ...
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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 ...
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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 ...
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1answer
273 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 ...
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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 ...
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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 ...
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182 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 ...
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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=...
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535 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 ...
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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 ...
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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 ...
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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 ...
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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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789 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}$...
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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 ...
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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 ...
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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 ...
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50 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–...
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4answers
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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,...
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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 ...
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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 ...
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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 ...
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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 ...
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Phosphates Functional Group

In my text book it states that a phosphate group is considered to be $\ce{-OPO3^{2-}}$. However, online it states that phosphate is $\ce{PO4^{3-}}$. Why do these contradict? Am i confusing phosphate ...
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183 views

Reference request - Nomenclature of organophosphorus compounds?

Can someone please provide me a good reference for the nomenclature of organophosphorus compounds such as pesticides and chemical warfare agents? Something from the IUPAC would be great. Thanks.
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Why does fluorine act as a leaving group in organophosphates?

C-F bond is the strongest single bond in organic chemistry with a bond energy of $\ce{453 kJ\,mol^{-1}}$. And it is very difficult to break this bond and F does not act as a leaving group. However, ...
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Does the synthesis of beta-keto phosphonates from esters have a name?

Consider the Horner–Wadsworth–Emmons reaction; one of its reactants is a phosphonate, usually stabilised by a β-carbonyl group which is then deprotonated in α position (figure 1). These ...
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1answer
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Why are phosphate-phosphate bonds weaker than phosphate-water bonds?

According to the Wikipedia entry on ATP, ATP is an unstable molecule in unbuffered water, in which it hydrolyses to ADP and phosphate. This is because the strength of the bonds between the ...
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Why is ATP, but not ADP or AMP, a sole source of energy?

Why are three phosphate groups (such as in ATP) required for release of energy, but not two (ADP) or one (AMP) phosphates? How does breaking the phosphate bond release energy?
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Clarifications about the mechanism of the Wittig reaction [closed]

Ok so this is the proposed mechanism for the Wittig Reaction as stated by my textbook, LG Wade. I have some doubts regarding this mechanism: 1) Why is only triphenyl phosphine used here? Why not ...
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1answer
81 views

How exactly is energy created by oxidative phosphorylation

I understand how the protons and electrons move around through various carriers, shuttles and proteins, but there's this talk of electrons being in "lower in energy" at the end. What does that mean? ...
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Why is DNA negatively charged and what makes it so?

What part in the strand contributes to the overall non neutral charge? DNA is not isolated in the body, so what keeps it stable while being charged? Why is it important for DNA to be charged?
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When are the terms diphosphate and pyrophosphate used?

On the Wikipedia article about pyrophosphate, it states that: The group (pyrophosphate) is also called diphosphate or dipolyphosphate. But for example, why is ADP apparently called adenosine ...
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Why are so many different organophosphates able to deactivate acetylcholinesterase?

From sarin to tricresyl phosphate, there are organophosphates that are able to deactivate acetylcholinesterase. What's so special about the simple organophosphate group that makes them able to do it?
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Why is the nomenclature glucose 6-phosphate, not 6-phosphateglucose?

What exact nomenclature rule define the naming of glucose 6-phosphate?