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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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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 $\alpha,\beta$-...
GingerBadger's user avatar
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6 votes
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Treatment of ketones with excess Tebbe reagent

The reaction in black below was presented in a set of lecture notes as an example of the use of the Tebbe reagent, however it's not immediately obvious (to me, at least) that the product should be the ...
NotEvans.'s user avatar
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I found transition states (TS), but calculations aren't supported by experiment. Do I look for more TSs or somewhere else?

I'm using Gaussian to investigate a catalyst system. Experimental evidence showed that one of three analogues (R = phenyl, Ph), yielded a benzosultam when treated with 2,4,6-...
Amotttier's user avatar
6 votes
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387 views

Why do catalysts have limited turnover numbers in practice?

I quote the Wikipedia page definition for Turnover number: In other chemical fields, such as organometallic catalysis, turnover number (abbreviated TON) has a different meaning: the number of moles ...
k--'s user avatar
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NO coordination linear vs bent - valence electron

I'd like to count the total valence electron of following neutral complex in the ionic counting (=donor-pair): Electron count: $$\begin{align} \ce{Cp-} : \ce{6e-} \\ \ce{CH3-}: \ce{2e-} \\ \ce{PPh3} :...
laminin's user avatar
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5 votes
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Why transition metal catalyzed [2+2]cycloaddition reactions allowed?

As you know, cycloaddition reactions which (4n)π electrons are involved in such as [2+2]cycloaddition are forbidden in normal organic reactions, but transition metal catalyzed [2+2]cycloaddition ...
Yossy's user avatar
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Is it possible to do Cobalt catalyzed directing group asisted meta C-H functionalization of arenes

Directing Group assisted Pd catalyzed (sp2)meta-C-H functionalization has a growing attention in recent years. In addition, few examples can be found for meta-C-H functionalization via Rhodium. I am ...
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Sodium Naphthalenide

The sodium fusion test done in the lab for the systematic identification of a given organic compound is basically fusing sodium metal in a fusion tube, and then adding the compound in a small quantity,...
Eashaan Godbole's user avatar
5 votes
0 answers
177 views

Regioselectivity in Ziegler–Natta polymerisation of α-olefins

Why does the Ziegler–Natta polymerization display the regioselectivity shown in the image? Internal nucleophiles (coordinated to the metal) should attack the alkene on the less substituted end, like ...
EJC's user avatar
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Aluminium isopropoxide electronic structure

From Wikipedia: A tetrameric structure of the crystalline material was verified by NMR spectroscopy and X-ray crystallography. The species is described by the formula $\ce{Al[(μ-O-i-Pr)2Al(O-i-Pr)2]3}...
MichaelK's user avatar
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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 ...
CuriousTree's user avatar
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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 ...
organometallo's user avatar
4 votes
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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 ...
user1155386's user avatar
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Why do heavy metals like mercury and lead have an affinity for sulfur or sulfur compounds?

Many of the heavy metals such as mercury, lead, thallium, cadmium, and arsenic exert toxic effects largely by binding to or otherwise interfering with organic sulfur compounds or groups in the body. ...
amylakin's user avatar
4 votes
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686 views

Why doesn't beta hydride elimination happen in alkenyl/aryl halides?

Beta hydride elimination is an important reaction in organometallic chemistry: This reaction prohibits the use of saturated alkyl halides in coupling reactions, because it can take place after ...
EJC's user avatar
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Can 0-Carborane be stored at room temperature?

I am a physics post-doc at Oak Ridge National Lab (with a bit more training in chem than the average physicist). I ordered a small sample of o-Carborane from Sigma-Aldrich to test for doping liquid ...
James Matta's user avatar
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Why doesn't β-elimination occur in Cr(CMe3)4?

By $\beta$-elimination, I am refering to the reaction where a M-C-C-H structure reduces to ($\eta^2$-alkene)-M-H. My lecture notes claim that $\ce{Cr(CMe3)4}$ is stable and does not incur such ...
이희원's user avatar
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237 views

Why does Co(CO)4 exist as dimeric Co2(CO)8?

I was wondering why is this equilibrium below established at all... Why can't Co(CO)4 exist on its own, as a monomer?
Rudransh Sinha's user avatar
3 votes
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325 views

Driving force in Corey-House reaction

In my textbook of organic chemistry by francis carey 11th edition, the Corey-house synthesis is elaborated on in the topic of organocopper reagents. It is mentioned that as the R-X alkyl halide is ...
ImJustKawaii's user avatar
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215 views

Why is the 2-bond (Sn-H) coupling constant larger than the 3-bond Sn-H coupling constant for tetraethyltin?

I was looking at the NMR spectrum of tetraethyltin [$\ce{Sn(CH2CH3)4}$], and found that the $\ce{Sn-H}$ coupling constant between $\ce{Sn}$ and $\ce{CH2}$ is larger than that between $\ce{Sn}$ and $\...
S R Maiti's user avatar
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3 votes
0 answers
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Why can zinc porphyrins assume 5 coordinate geometries?

It has been reported that 5-coordinate geometries are possible and stable for Zn(II) porphyrin complexes. How do these complexes form and why are they stable when other 5-coordinate geometries of Zn(...
Tiocfaidh's user avatar
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Reactivity of unsaturated organolithium compounds

I'm particularly looking in the context of alkyl lithiums compared to vinyl-lithiums and alkynyl-lithiums. Why is it that shifting from sp3 to sp2, and even further to sp carbanions, reduces the ...
FriendlyGlove's user avatar
3 votes
0 answers
97 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 ...
Secret's user avatar
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49 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 ...
Kemono Chen's user avatar
3 votes
0 answers
121 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?
Sharv Laad's user avatar
3 votes
0 answers
310 views

What does unactivated, activated and deactivated aryl chloride mean in cross-coupling reaction?

Hartwig et al. [1] used unactivated aryl chloride for Buchwald–Hartwig amination. What does unactivated, activated and deactivated aryl chloride mean in a cross-coupling reaction? Reference Hartwig, ...
Cherry's user avatar
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3 votes
0 answers
1k 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.
Carrick's user avatar
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3 votes
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133 views

Selectivity of olefin cross-metathesis reaction

I'm looking at the reaction shown below which uses a ruthenium catalyst: I am confused because the ruthenium catalyst which is used in the reaction should be Z selective due to the features on the ...
Jones78's user avatar
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Are there any stable complexes where an (N-unsubstituted) imine is bound eta^2 to a (late) transition metal?

I've been looking for an example of a stable complex where a $\ce{C=N}$ is coordinated $\eta^2$ to a (late) transition metal, but could not find any. Do they exist at all? For $\ce{C=C}$ there are ...
snurden's user avatar
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3 votes
0 answers
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Cycloaddition of Silyl Dienol Ethers with Sodium Bromodifluoroacetate: What's the scope?

I have recently came across this article "Copper(I)-Catalyzed [4 + 1] Cycloaddition of Silyl Dienol Ethers with Sodium Bromodifluoroacetate: Access to β,β‐Difluorocyclopentanone Derivatives". (Org. ...
Oanes Andrei's user avatar
3 votes
0 answers
1k views

Iodine/ Magnesium Exchange reaction?

Traditional Grignard reagents are made by reacting alkyl halide with Magnesium metal. However, the preparation and scope of their application have been limited because of low functional group ...
Khan's user avatar
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3 votes
0 answers
2k views

Classes of Organometallic Compounds - Where do I put Grignard Reagents?

[Note- I've already seen this question Why do Magnesium and Lithium form *covalent* organometallic compounds? as user Mithoron was kind enough to point out, but the problem that I face is different ...
paracetamol's user avatar
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3 votes
1 answer
111 views

Siiloxane polymer experiment

I believe the first reaction would be a substitution of $\ce{SiMe3}$ for $\ce{I}$ and creating $\ce{SiMe3Cl}$. The second process I think would involve the $\ce{Mg}$ removing the two $\ce{Cl}$ and ...
Alex's user avatar
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2 votes
0 answers
64 views

Can other metal salt compounds besides copper sulfate/zinc sulfate be used to create chlorophyllin? E.g. the magnesium center is replaced

There has been a lot of research done into sodium copper chlorophyllin. The synthesis is quite simple and can be done at home. It involves extracting the chlorophyll, saponifying the solution, adding ...
tomatopies's user avatar
2 votes
0 answers
31 views

High kinetic basicity of alkoxides compared to alkyls

I'm reading something at the moment where they state: This reagent has enhanced basicity as it benefits from the high kinetic basicity of alkoxides compared to alkyls. This is in the context of ...
FriendlyGlove's user avatar
2 votes
0 answers
65 views

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 ...
Planejerle18's user avatar
2 votes
0 answers
789 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: ...
Ignas Pakamorė's user avatar
2 votes
0 answers
40 views

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 ...
matt_black's user avatar
2 votes
0 answers
212 views

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 ...
ETS's user avatar
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2 votes
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603 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-...
QuestionCookie's user avatar
2 votes
0 answers
33 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 ...
Benjamin Weiser's user avatar
2 votes
0 answers
2k 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 ...
Zen's user avatar
  • 21
2 votes
0 answers
42 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 ...
juno's user avatar
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2 votes
0 answers
703 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 ...
Don_S's user avatar
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2 votes
0 answers
102 views

Synthesis of a tungsten carbene bromide from [CpW(CO)3]-

I'm currently working through past test and exam papers in order to prepare for my organometallic test at the end of the month, but unfortunately I've gotten stuck on the following question. Since I ...
Lenard Carroll's user avatar
2 votes
0 answers
637 views

Selectivity in Suzuki coupling of 2,4-dichloropyrimidine

I've seen many papers (see e.g. Synthesis 2010, 16, 2721–2724) in which the 4-chloro group of 2,4-dichloropyrimidine is selectively reacted under Suzuki coupling conditions. Is there any way where ...
linezolid's user avatar
2 votes
0 answers
703 views

Trends in the covalency of bonding across the transition metals

I am under the impression that the covalent character in the bonding of transition metal compounds increases across a group; in fact I think this is why they're called transition metals (a transition ...
RobChem's user avatar
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2 votes
0 answers
101 views

Shelf Life of Methylcyclopentadiene

We are making organometallics in the lab, but instead of just regular Cyclopentadiene dimer, we crack methylcyclopentadiene dimer to make methylcyclopentadiene. I cannot find the shelf life of ...
ajs's user avatar
  • 31
2 votes
0 answers
58 views

Why does Pb(II) promote ligand substitution?

I have heard of an article where divalent lead $\ce{PbL2}$ ($\ce{L}$ is ligand) reacts with something (again not sure, as I dont know the article) and what it reacts with gains a ligand. In less ...
chemq's user avatar
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2 votes
0 answers
201 views

Make pure phthalocyanines from phthalocyanine dyes

We need a pure copper phthalocyanine for our experiments. Of course, we can buy it from Sigma Aldrich, but this means we'll have to wait a while. In local area we can buy only dyes which are about 98% ...
KOLANICH's user avatar
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