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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48 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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176 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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43 views

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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32 views

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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27 views

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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38 views

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
57 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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28 views

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
77 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
66 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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42 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 ...
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1answer
100 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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31 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 ...
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263 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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25 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 ...
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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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33 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{...
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107 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
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1answer
61 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 ...
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1answer
418 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
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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
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1answer
102 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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300 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 ...
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264 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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27 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 ...
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223 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
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. (...
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42 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 ...
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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?
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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 ...
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1answer
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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,...
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86 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 ...
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1answer
954 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 ...
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438 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 ...
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1answer
84 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 ...
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1answer
116 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:...
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535 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.
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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 $\alpha,\beta$-...
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554 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: ...
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347 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.
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119 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 ...
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2answers
148 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 $...
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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 ...
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1answer
410 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 ...
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475 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
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1answer
857 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 ...
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1answer
95 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 ...
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2answers
599 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, ...
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192 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 ...