Questions tagged [organometallic-compounds]
For questions relating to organic compounds which contain a bond between a carbon atom and a metal.
141
questions
4
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0answers
25 views
Further reading on photoconductivity of hemoglobin
I recently ran into this paper which describe experiments that confirm that hemoglobin is photoconductive. Finding this fact as incredible, I wanted to read up more on photoconductive properties of ...
2
votes
0answers
36 views
Why doesn't Grignard reagent attack alkyl halides [duplicate]
When we add magnesium to
alkyl halide, Grignard reagent is formed. $$\ce{R-X + Mg -> RMgX } $$ It is highly nucleophilic in nature. Now at this time the electrophilic alkyl halide is also present ...
2
votes
1answer
58 views
How does 1-bromo-2-fluorobenzene react with lithium amalgam? [closed]
How does this organometallic reagent react with 1-bromo-2-fluorobenzene? Does it react like Grignard reagent? If the product of this reaction is then reacted with furan, what will be the final product?...
3
votes
0answers
29 views
On the stability of methyl mercury
Question: Given that $\ce{Zn, Hg}$ are in the same group, how to explain that $\ce{Hg(CH3)}$ is stable but $\ce{Zn(CH3)}$ is unstable and $\ce{Hg(CH3)Cl}$ is stable? $\ce{Hg(CH3)}$ seems to have an ...
3
votes
1answer
97 views
Will ferrocene undergo electrophilic aromatic substitution?
Ferrocene has two structure 1 and 2.It is bonded to an aromatic ion cyclopentadienyl anion.Aromatic species such as benzene , cyclopentadienyl anion undergo electrophilic aromtic substitutions.
Then,...
1
vote
0answers
23 views
Alkyl insertion with cobalt and CO
Reaction of $\ce{(Cp)Co(Me)2(CO)}$ in the presence of excess $\ce{CO}$ yields two different organic products, $\ce{A}$ and $\ce{B}.$ The only metal-containing product is $\ce{(Cp)Co(CO)2}.$ The IR ...
2
votes
0answers
19 views
Will lead bind to dissolved polymer (Kapton) monomers?
We are attempting to determine the concentration of lead impurities in Kapton. Essentially we need to extract lead in the tape polymer Kapton (structure seen below);
The amount of lead in the tape is ...
1
vote
0answers
29 views
Electron-donating trends for ligands bound to metal complexes
Imagine an inorganic complex with a bunch of terminal ligands. All else the same, would $\ce{F-}$ or $\ce{Br-}$ ligands be more electron-donating and why?
Of course, in terms of $\mathrm{p}K_{\mathrm{...
11
votes
0answers
95 views
Can pi backdonation occur on non-metal centers?
The common example of back-donation is the interaction of a CO molecule with a metal center (d-orbitals) on a surface.
Can a similar mechanism occur between CO and a non-metal center, like oxygen on ...
2
votes
1answer
50 views
N-heterocyclic carbene metal complexes. Question about the delocalization of the nitrogen lone pairs
I am wondering why nitrogen lone pairs are delocalized in NHC metal complexes. What I can think of is, when complex is formed, plus charge is formed on the carbon atom and therefore delocalization ...
6
votes
1answer
235 views
Why do aromatic compounds have an upfield shift upon coordination to metals?
Why do aromatic compounds have an upfield shift upon coordination to metals e.g. ferrocene? The 1H NMR shows a single environment at ~4.1 ppm. This is in contrast to the usual aromatic shift of ...
4
votes
1answer
1k views
Grignard Reagent in THF vs in Diethyl ether
While learning about the Grignard reagent I was taught this by my teacher, but I couldn’t justify why it was so..
I cannot see how Grignard reagent would react differently in basically an ethereal ...
2
votes
1answer
87 views
Is an alcohol-based spray cleaner ok for cleaning an aluminum heat exchanger?
Simple alcohols such as ethanol can, apparently, corrode aluminum. However, this corrosion reaction seems to be very slow at room temperature and below. Is an ethanol based, non-foaming spray cleaner, ...
2
votes
0answers
162 views
Why does LDA solution gradually turn dark brown?
LDA (lithium diisopropylamide) solution in THF/hexane gradually turns red-brown liquid. Especially commercially available one is extremely dark red-brown. What makes it brown?
I've searched online ...
1
vote
0answers
185 views
Reaction of grignard with beta Keto ester [closed]
A reaction takes place between $\ce {CH3COCH2COOC2H5}$ with 4-chlorophenyl magnesium bromide, followed by acidic work-up. What will be major product of the reaction? Would the product be the same as ...
2
votes
0answers
24 views
How to calculate the magnetic exchange coupling in a charged radical complex?
I have a neutral complex with two magnetic centers. For this case it is easy to calculate the exchange coupling as the broken symmetry state is converged properly. But when I am making the complex ...
2
votes
0answers
150 views
What makes dimethylmercury ((CH3)2Hg) so penetrative through latex and human skin?
I've read the story of Karen Wetterhahn and how she was poisoned and died from two drops of dimethylmercury that accidentally fell on her latex glove, and I was wondering what is the chemical ...
4
votes
1answer
54 views
Is it possible to have a ferrocenol?
I'm specifically talking about having a hydroxy- group on the ferrocene ring.
Is it simply impossible because the ring is anionic?
I haven't seen any hydroxyferrocene molecules available online. (...
2
votes
1answer
39 views
How do we know cyclopentadienylmolybdenum tricarbonyl occurs as a dimer?
Cyclopentadienylmolybdenum tricarbonyl, $\ce{MoC8H5O3}$, dimerizes to form the cyclopentadienylmolybednum tricarbonyl dimer, $\ce{(MoC8H5O3)2}$.
$\hspace{3cm}$
How was it discovered that it does ...
3
votes
0answers
71 views
Do Sodium Alkynides react with esters in the same way that Grignard reagents do?
We know that Sodium alkynides react with aldehydes and ketones like Grignard reagents. But do they behave the same way with esters?
10
votes
1answer
121 views
How can the solid state structure of cyclopentadienyllithium be explained?
In the solid state, LiCp adopts a polymeric multidecker structure where Li atoms are sandwiched between two Cp rings (shown in this diagram from Organometallics 1997, 16 (17), 3855–3858):
If we ...
2
votes
1answer
2k views
How to electron count bridging ligands?
Although I am okay with rationalising bridging halides and $\mu$-2 CO I can't seem to figure out others, including $\mu$-2 hydride, CN- and NO.
When considering the electron count of bridging ligands,...
1
vote
0answers
69 views
What does unactivated, activated and deactivated aryl chloride means in cross-coupling reactions?
When I read this literature https://pubs.acs.org/doi/pdf/10.1021/jo990408i, it used unactivated aryl chloride for Buchwald-Hartwig amination.
What does unactivated, activated and deactivated aryl ...
10
votes
1answer
596 views
Mechanism of lithium-halogen exchange of primary alkyl iodide
On Clayden's page 190 this reaction is given for preparation of organometallics:
What is the mechanism of this reaction? I expected the "almost carboanion" part of the $\ce{t-BuLi}$ to attack as a ...
4
votes
2answers
373 views
How does the Wurtz reaction produce alkynes?
Wikipedia mentions that alkynes can be produced from geminal dihalides through the Wurtz reaction. However, I am unsure of the reaction mechanism for this reaction. I have not been able to find any ...
2
votes
1answer
83 views
What is the product of magnesium reacting with carbon?
$$\ce{Mg + C -> X}$$
$$\ce{X + H2O -> Y}$$
Determine unknowns X and Y.
Now the problem is I think the answer should be $\ce{X=MgC2}$ and $ \ce{Y=C2H2 + Mg(OH)2}$. But the given answer was ...
2
votes
1answer
103 views
One-pot synthesis of pyrazole [closed]
I am trying to follow a published paper. It is a one-pot synthesis of pyrazole from a ketone and and acid chloride via a diketone intermediate.
Here is the produre from the paper:
General Procedure:...
3
votes
0answers
399 views
Mechanism for reaction of an allene with the Grignard Reagent(RMgX)
How does the Grignard Reagent($\ce{RMgX}$) react with an allene $\ce{CH_2=C=CH_2}$ and what are the products formed?
This is exactly what I tried to do.
Any help will be appreciated.
7
votes
0answers
67 views
How can organocuprates generated with catalytic Cu(I) be competitive in 1,4-addition to an enone?
Organocopper compounds (e.g. $\ce{LiCuR_2}$) are often prepared from an organolithium or Grignard reagent when a soften nucleophile is needed, such as for a conjugate addition to an $\alpha,\beta$-...
5
votes
1answer
471 views
Why are 3 equivalents of organolithium needed in synthesis of ketone from carboxylic acid?
For the reaction of a carboxylic acid and organolithium reagents to synthesise a ketone, Clayden's, on p 219, mentions:
Notice that three equivalents of organolithium are needed in this reaction: ...
-1
votes
1answer
300 views
electron counting for transition metal-oxo ligand compound
Using donor-pair method, how many electrons would an oxo ($O^{2-}$) ligand contribute? I cannot decide if it is 2 or 4.
3
votes
1answer
111 views
Is associative ligand exchange possible with octahedral complexes?
Can associative ligand exchange produce an octahedral intermediate as long as the initial complex has 16 electrons (unsaturated)?
Not sure. all I ever see is a square planar turning into a trigonal ...
14
votes
2answers
144 views
Mechanism of a Gold catalyzed organometallic reaction: Confusion regarding the last step
I needed to draw the reaction mechanism for this reaction:
So, after consulting some literature I drew this mechanism:
But, I am not sure about the last step. Does the $\ce{H+}$ just substitute the $...
1
vote
0answers
62 views
Looking for a low boiling point solvent for MAPI precursors (Lead Iodide (II) and Methylammonium Iodide) [closed]
Things I have thought of till now:
Acetonitrile with HI additive
Acetonitrile with DMSO additive
The problem with the first would be that HI is in an around 55% aqueous solution and water doesn't ...
17
votes
1answer
311 views
How to name this quintuply-bonded chromium dimer?
Depicted below is a chromium compound with a metal–metal quintuple bond. It boasts two identical bridging ligands, derivatives of 1,3-diphenylbenzene. The aim of this question is to figure out
the ...
2
votes
0answers
409 views
C-O bond strength in metal carbonyls [duplicate]
The metal carbonyls (and similar organometallic compounds) involve a combination of a $\sigma$-bond, a $\pi$-bond and backbonding. The bond strengths under consideration are the metal-carbon bond and ...
14
votes
1answer
836 views
Are there any significant uses of the compound formed by magnesium and anthracene?
In an unusual reaction, magnesium reacts with anthracene in THF to form a grignard-like compound called, prosaically, magnesium anthracene:
I remember using it briefly in the 1980s. At the time there ...
1
vote
1answer
88 views
How to reconcile conflict between assumed oxidation state and the most stable multiplicity from electronic structure calculations?
Consider either of the small, neutral molecules containing two Zn atoms below. If I were to determine the oxidation state of Zn from this molecule, I would formally assume each Zn to be Zn(I) in order ...
3
votes
2answers
527 views
Which complex is the most stable?
Between $\ce{[Rh(Ph2PCH2PPh2)3]^{3+}}$ and $\ce{[Rh(Ph2PCH2CH2PPh2)3]^{3+}}$, which one is the most stable thermodynamically? I think it's about the size of the chelate ring effecting their stability, ...
8
votes
1answer
182 views
Ketone/aldehyde synthesis from N-acylazetidines or aziridines
A common principle in organic chemistry is to make sure the product is less reactive than the starting material, to prevent overreaction. So, for example, the treatment of an ester with a Grignard ...
0
votes
1answer
515 views
Chemical function of Mg and Conjugated bonds in Chlorophyll [closed]
This question has 3 parts, each related to the title.
In biochem, we were shown the chemical structure of chlorophyll. The light-absorbing head has many carbon-rings with alternating single and ...
1
vote
1answer
2k views
What's the explanation for the chelate effect? [duplicate]
I got that multidentate ligands form more stable coordination complexes than monodentate ligands, but why?
1
vote
0answers
35 views
Complexation of hydroxy chalcone oxime with metal [closed]
Does the complexation of 2-hydroxy chalcone oxime (below) with a metal require any catalyst? Is the complexation pH sensitive?
-1
votes
1answer
160 views
What is the systematic name of ammonium bisoxalato cuprate (II)? [closed]
What is the systematic name of ammonium bisoxalato cuprate(II)?
I already tried $\ce{(NH4)2[Cu(C2O4)2]^{2+}}$ but i am uncertain if that answer is correct.
6
votes
1answer
566 views
How are Grignard reagents stable in an ethereal solution? [duplicate]
I have heard of the leveling effect, which mentions that highly basic ions cannot exist in a solvent if it's acidity is high enough to be deprotonated by the base.
Considering that, check out the ...
2
votes
1answer
209 views
Why does a smaller bandgap correlate to increased absorption of visible light?
I am currently involved in a project on metal organic frameworks in my AP chemistry class, and specifically their applications in $\ce{CO2}$ reduction into formate. All the explanations we can find on ...
1
vote
2answers
79 views
Is it safe to lyophilize/Freeze-dry a chelated compound?
I have a compound that consists of a metal ion chelated by a linear organic structure with assorted moieties in aqueous medium. I'd like to dehydrate this mixture fully to get solid product, but ...
8
votes
2answers
849 views
Is the term “heteroatom” reserved for exclusive elements?
From my experience, typically in organic chemistry, the implication of "hetero-atom" in some molecule is understood as B, N, O, S, P or a halogen -- or any nonmetallic element, perhaps.
If one ...
12
votes
1answer
421 views
Noyori hydrogenation and the Curtin–Hammett principle
My question is relating to how the Curtin–Hammett principle applies to homogeneous hydrogenation using chiral ligands.
Figure 0: An example of a quadrant diagram used as a mnemonic to predict the ...
1
vote
0answers
849 views
CO stretching frequency band in the IR spectrum for tetracarbonylnickel and tetracarbonylferrate(II)
A past exam question says:
With reference to the main bonding interactions between a transition
metal and a terminal $\ce{CO}$ ligand, explain whether you would expect to
observe a lower $\ce{...
