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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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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 ...
11
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1answer
366 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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1answer
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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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1answer
39 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 ...
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0answers
26 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 ...
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11 views

Are polysulphates more(or less) susceptible to hydrolysis than polyphosphates?

To clarify, when I speak of polysulphates(not sure if that's the correct term or if sulphate ester is the proper term) I'm talking about molecules like: ...
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43 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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1answer
231 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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1answer
726 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 ...
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1answer
2k views

What is the difference between metaphosphoric acid and phosphonic acid?

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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1answer
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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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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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2answers
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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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1answer
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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 ...
8
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2answers
240 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 ...
12
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1answer
784 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 ...
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2answers
869 views

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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1answer
120 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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2answers
1k views

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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3answers
505 views

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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2answers
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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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1answer
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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
67 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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3answers
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Why DNA is 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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3answers
4k views

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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2answers
143 views

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?