Questions tagged [organometallic-compounds]

For questions relating to organic compounds which contain a bond between a carbon atom and a metal.

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0answers
7 views

Reaction of potassium sorbate with bayer [closed]

what is the solution of this reaction (Bayer's reagent) potassium sorbate + MnO4- + H2O = ?
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What property of a Cu(II) metal centre makes it suitable to form a complex with a bipy ligand? [closed]

Could someone please help me out- what properties of Copper (II) makes it a good metal centre for a molecule? The ligand is bipy. Thanks :)
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Can someone help with the nomenclature of this metal complex. MarvinSketch is giving me trouble

I’m trying to get a name for the structure above using MarvinSketch for my undergraduate senior thesis. This is the first time I’ve had to draw a metal complex in MarvinSketch, and I’m having trouble ...
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Is there a posibility for a substituted squaramide to be hydrolysed during an aqueous work up? [closed]

I have made substituted squaramides from diethyl squarates. But surprisingly, I noticed that it is decomposing after an aqueous work up giving the amines back.
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1answer
46 views

Weinreb ketone synthesis [closed]

For this problem, Can I use weinreb ketone synthesis? I found the product but not sure it is the right one If the amide react with either R1-Mgbr or R2-Li, then it produces the ketone?
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1answer
69 views

Wittig reaction in presence of carboxylic acids

The following reaction came in a recent test: According to this reaction, the acidic hydrogen would protonate the ylide, and the standard wittig reaction would not take place. This source agrees with ...
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50 views

Metal coordination in enzymes: What type and number of bonds form between amino acid residues and Fe(II)?

My understanding: Transition (d-block) metals, as found in intracellular proteins, are limited to about 10 elements including amongst others Fe, Ni, and Cu. Due to the reductive environments inside ...
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1answer
58 views

Preparation of Grignard reagent. Free radical rearrangement

Mechanism of formation of Grignard Reagent $$\ce{R-X + ^.Mg^. ->[\text{r.d.s.}] R^. + ^.Mg+X-} $$ $$\ce{R^. + ^.Mg+X- -> R-Mg+X-} $$ As the mechanism of preparation of Grignard reagent suggests,...
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55 views

In which condition CO uses the oxygen end for bonding?

Generally Metal Carbonyl complex are formed from Carbon end. Is it possible under some specific condition that the Oxygen end is used? (PS -I know about the structures of M-CO bonding)
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1answer
38 views

What would be the product of following elimination reaction?

Question Doubt The answer is given B. But why cant it be C after all formation of cyclopropane would increase angle strain?
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106 views

How do you optimize an organo-metalic compound containing cerium in in Gaussian?

I am trying to perform optimisation of the molecule attached. I need to get partial charges and frequencies. The issue is that it doesn't converge with following input: ...
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What is the difference between a dπ-dπ and delta bond [closed]

I have always been wondering the difference between a dπ-dπ bond and a delta bond. What are the situations that either bond is formed in overlap of two d orbitals.
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Can ferrocene type sandwich compounds be made with fluorene?

Ferrocene will be well known to made members of this site. It consists of two cyclopentadienyl anions sandwiching an iron-II ion. During my first year organic chemistry course (about 40 years ago) I ...
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1answer
25 views

Reaction of grignard in presence of Halogen [closed]

What happens when a Ketone say $$RCOCH3$$ on reaction with grignard reagant in presence of X2 (halogen) what happens?? Can someone please explain
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Curtin-Hammett principle to evaluate alkene insertion

Given an unsymmetrical alkene in a simple non-stereoselective catalytic hydrogenation reaction. If one would want to investigate the nuances in the catalytic cycle of a dihydride complex leading to ...
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1answer
61 views

Reason for double acylation of ferrocene only occurring with certain reagent combinations

Can anyone explain why the acylation of ferrocene produces the following results: Ferrocene + acetic anhydride + AlCl3 ==> mono-acylated ferrocene but: Ferrocene + acetyl chloride + AlCl3 ==> di-...
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Are there many examples of stable, well characterised organometallic compounds of saturated hydrocarbons with beta hydrogens?

One of the first things you tend to learn in organometallic chemistry is that transition metal compounds containing beta-hydrogens are unstable (there are plenty of stable main groups ones; eg ...
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1answer
42 views

Organometallic and oxygen

I often read that reactive organometallics must be handled under an inert atmosphere because they react with oxygen in the atmosphere. This applies to grignard reagents, organolithium reagents, and ...
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Reaction mechanism of lithiated benzene and oxygen in acid

According to (1) addition of O2 in acid to lithiated benzene makes phenol. I'm trying to deduce the mechanism, and somehow it doesn't feel right but I'm not sure. (1) Snieckus, V. Directed ortho ...
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1answer
108 views

What is the mechanism of this reaction?

I've been stuck with this for some time. I just don't see it. As the reactant is Pd(0), I think oxidative addition will happen to the bromine. Then I would say an insertion reaction happens. However ...
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1answer
123 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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1answer
291 views

What is the oxidation state of copper in Gilman's Reagent? [closed]

What is the oxidation state of copper in Gilman's reagent? In $\ce{R-Cu}$ bond the oxidation state is +1. Thus in $\ce{R-Cu-R}$ bond the oxidation state has to be +2. But if that so why positive $\ce{...
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262 views

Volatile alkali metal compounds

Most elements are or have compounds that are gases or have a significant vapor pressure at room temperature. Fluoride is a powerful tool for producing highly oxidized covalent and volatile compounds. ...
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How does electrophilic bromination with 1,2-dibromoethane work?

Hi I am trying to figure out the mechanism of a reaction containing a lithium carbanion and 1,2-dibromoethane in THF. The lithium carbanion is generated by deprotonating using LDA. Then 1,2-...
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Why do statistical effects impact stepwise stability constants?

I have a question regarding the stepwise stability constants of metal complex formation/substitution. My lecture notes say that if we have a metal complex, say $\ce{[MX_{6}]}$, and a substitution ...
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Why CO is a weak pi-acid ligand?

This question was given by my chemistry professor, but I doubt that this question is not correct. Following the lewis definition of the acid, any molecule or atom acts as a acid if it accepts an ...
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Organometallic Synthesis: Cp2Ti(I)Me from TiCl4

I've been working on this synthesis question for a couple days but I'm a little stuck. The question is: Using only $\ce{TiCl_{4}}$, $\ce{NaCp}$, $\ce{PhLi}$, $\ce{MeI}$, and $\ce{EtMgBr}$, ...
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1answer
85 views

Why does cyclobutadieneiron tricarbonyl behave aromatically?

It is said that $\ce{(\eta^4-C4H4)Fe(CO)3}$ can undergo electrophilic substitution reactions. Therefore, it displays aromaticity. For the iron atom, it has $8$ electrons in its outer shell initially ...
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IRC analogue of conical intersections and minimum energy crossing points?

In my project, there are some spin forbidden organometallic reactions that involves both the triplet minima and singlet transition state (TS). Using the penalty method in qchem as well the method of ...
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1answer
289 views

Why there are more examples of carbonylate anions than metal carbonyl cations?

I know that metal carbonyl complexes that do not follow EAN rule or 18 electron rule try to achieve that by gaining electron (forming carbonylate) or loosing electron (forming carbonyl cations). But ...
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1answer
81 views

Why has nature evolved to put a porphyrin (i.e. chlorophyll) as the chromophore in a leaf? [closed]

I'm stumped by this question: Why has nature evolved to put a porphyrin (i.e. chlorophyll) as the chromophore in a leaf? I've thought that it might have something to do with how sun emits light ...
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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 ...
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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 ...
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1answer
269 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?...
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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 ...
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1answer
681 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,...
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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 ...
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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 ...
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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{...
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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 ...
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1answer
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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 ...
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1answer
741 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 ...
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1answer
4k 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 ...
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1answer
286 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, ...
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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 ...
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406 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 ...
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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 ...
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298 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 ...
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1answer
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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. (...
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1answer
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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 ...