Skip to main content

Questions tagged [organometallic-compounds]

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

Filter by
Sorted by
Tagged with
1 vote
1 answer
918 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 ...
3 votes
1 answer
133 views

Hydrogen in Organometallic Chemistry

In the book, The Organic Chemistry of Nickel : Organonickel Complexes by PW Jolly, the reaction between sodium hexacarbonyldinickalte(-1) and ammonia produces hydride complex. Some possible ...
0 votes
0 answers
45 views

Synthesis of Gilman reagent

So I will be refering to the image attached here while explaining my query. In the synthesis of Gilman reagent, in the 3rd step, my teacher told that the (R-) from RLi will attack the partially ...
11 votes
2 answers
617 views

Why doesn't sodium form organometallic compounds with alkyl halides?

Both magnesium as well as lithium, on reaction with an alkyl halide (say chloroethane), form an organometallic compound. However, sodium and potassium do not exhibit such a reaction. Instead of ...
10 votes
2 answers
351 views

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 ...
7 votes
3 answers
3k views

Nature of a1g Molecular Orbital Interactions in Ferrocene

While learning about ferrocene I've come across this molecular orbital diagram. What particularly confused me is the nature of the a'1g orbital. My professor taught that a'1g and e2g are considered ...
9 votes
1 answer
570 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. ...
0 votes
0 answers
23 views

Binding energies of transition metals in the 3d series

Binding energy of the transition elements in the 3d series increases up to vanadium then drops from chromium to manganese and then increases slightly and then drops again It is seen that binding ...
2 votes
1 answer
167 views

Effect of particle size on yield of copper acetylide

To avoid pure trial and error, I need some examples of experiments already done with (possibly ammoniacal) aqueous solutions, particles/precipitates of copper (both oxidation states) salts, and ...
6 votes
1 answer
8k views

Grignard Reagent in THF vs in Diethyl ether

I cannot see how Grignard reagent would react differently in an ethereal solvent. While learning about the Grignard reagent I was taught this by my teacher, but I couldn’t justify why it was so. I ...
-2 votes
1 answer
86 views

Why is Chromium hexacarbonyl diamagnetic?

So there was a question in coordination chemistry regarding the nature of $\ce{[Cr(CO)_6]}$ The book had the question under VBT and solved it using "strong ligands cause all electrons to pair up&...
7 votes
3 answers
15k 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,...
4 votes
2 answers
2k views

Why do organolithium and organomagnesium compounds react differently with CO2?

My textbook doesn't say anything about this but does say that on addition of organolithium compounds to carbon dioxide, they give ketones and not carboxylic acids like grignard reagents. This has been ...
3 votes
0 answers
51 views

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 ...
6 votes
1 answer
864 views

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 ...
0 votes
0 answers
35 views

Is Polymerized lithium niobocene a possible compound? [duplicate]

I was doing some research on different types of body armor and found a fictional compound by the name of Polymerized LiNb. I wanted to find what the structure of this compound looked like so it could ...
1 vote
2 answers
139 views

How did Sinclair Oil put "liquid nickel" into gasoline, and what were the chemical mechanism(s) by which it was supposed to reduce engine wear?

The April 22, 2022 Veritasium video The Man Who Accidentally Killed The Most People In History is worth a watch, and was the basis for the question Why would tellurium + sodium hydroxide have worked ...
-2 votes
1 answer
65 views

What do the arrows mean in the Structural Formula of Oxaliplatin? [duplicate]

What do the arrows mean in the Structural Formula of Oxaliplatin? I haven't seen these and couldn't find anything explaining them.
0 votes
1 answer
73 views

1,4 (conjugate) addition in unsaturated aldehydes and ketones

When carbonyl compounds react with grignards, they usually give a 1,2 addition (direct addition) product. However, under certain conditions, they give conjugate addition (1,4 addition) product as the ...
3 votes
1 answer
69 views

Why are Mo(NR2)3 complexes isolobal with the nitrogen atom in N2

In a Molybdenum complex of the form Mo(NR2)3, the Mo is in the oxidation state of +3, leaving it with 3 d electrons. When combined with an additional 2*3 electrons from the ligands, this leaves it ...
2 votes
2 answers
227 views

Does ferrocenium chloride ([Fe(C5H5)2]Cl) exist as a stable compound?

I am interested in using ferrocenium chloride ($\ce{[Fe(C5H5)2]Cl}$) for a synthesis application, but I couldn't find any sources referring to its existence, even though some websites and a figure in ...
4 votes
1 answer
10k views

Why does magnesium form covalent bonds with carbon?

According to my professor, magnesium and lithium form covalent bonds with carbon but calcium does not. He did not elaborate. Why is this so? The electronegativities are: Mg — 1.31 Li — 0.98 Ca — 1 ...
6 votes
0 answers
12k views

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} :...
1 vote
0 answers
59 views

Amidine synthesis from nitrile and dimethylamine using n-Buli as a base

I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere. I have been doing the reaction and I can observe conversion of starting ...
0 votes
0 answers
101 views

What is the difference between zero-point and total energy of a molecule in the output of an ORCA FREQ calculation?

I am trying to find the enthalpies of formation for a couple organometallics in ORCA and as a first time user I am a bit bogged down in the terminology. The Gaussian manual has a section on these ...
0 votes
0 answers
22 views

Some advice on inorganic textbook [duplicate]

I'd like to have some advice on Inorganic textbooks. I've already consulted some books (Kettle, Drago, Keiter, Cotton) and they are all very useful, but now I'm searching for a textbook which focuses ...
-1 votes
1 answer
249 views

What is the difference between Charge transfer and Electron transfer? [duplicate]

This problem was given to me yesterday that What is the difference between Charge transfer and Electron transfer? I was taking it thesame though the professor have given me some hint that charge ...
5 votes
2 answers
778 views

Does Grignard reagent on reaction with PbCl2 give PbR4 and not PbR2?

I was told by my teacher that $\ce{RMgX}$ forms $\ce{PbR4}$ when it reacts with either $\ce{PbCl2/PbCl4}$ the later case is clear to me but why does $\ce{PbCl2}$ forms a compound of the form $\ce{PbR4}...
-1 votes
1 answer
289 views

Help with drawing an Molecular Orbital (MO) diagram for organometallic complex

I do not understand how to draw the MO diagram for this question, i appreciate any help you can give on my 3rd yr Chem. Have i understood this correctly? QUESTION: Using an MO bonding picture and ...
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, ...
1 vote
0 answers
140 views

Why are Sonogashira reactions moisture sensitive?

Exemple, aryl halide + TMS-acetylene in NEt3 + Pd[PPh3]2Cl2 or Pd[PPh3]4: The reaction does not form water at any time so its presence wouldn't shift the equilibrium. Neither TMS-acetylene or the aryl ...
3 votes
2 answers
7k views

Predicting bond-strength of metal carbonyls

The metal carbonyls (and similar organometallic compounds) involve a combination of sigma bond, a pi bond and backbonding. The bond strengths under consideration are the metal-carbon bond and the ...
4 votes
1 answer
248 views

What do these arrows mean in inorganic chemistry?

I tried looking for these arrows in the 3rd molecule starting from the left(Pd) online and in my notes but I couldn't find anything. Is Pd actually bonded to something?
1 vote
1 answer
96 views

Why is the sp3-sp3 reductive elimination between the R1 and norbornene in the Catellani Cycle ''not favorable''?

I have recently started reading a book about C-H activation and I cannot figure out why in the Catellani reaction cycle the R1-norbornene reductive elimination side reaction which can be a major issue ...
5 votes
2 answers
3k views

Will ferrocene undergo electrophilic aromatic substitution?

Ferrocene has two structures (1 and 2). It is bonded to the aromatic cyclopentadienyl anion. Aromatic species such as benzene, cyclopentadienyl anion undergo electrophilic aromatic substitutions. Then,...
15 votes
1 answer
246 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 ...
3 votes
0 answers
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?
5 votes
1 answer
146 views

Why is a ring carbon C-R of a substituted ferrocene more downshifted on 13C-NMR?

Upon assigning $\ce{^{13}C}$-NMR for 1,1'-bis(α-methylmethanol)ferrocene, we discovered the substituted FcC-CH peak (95.14 ppm) was more downshifted than the CH-OH peak (65.59 ppm) as was confirmed by ...
4 votes
1 answer
157 views

Polymer purification by reprecipitation troubleshooting

I am synthesizing new polymer that has not been reported before. The structure of the polymer is based on indacenodithienothiophene unit and thiophene. I used Stille polymerization. As monomers, I ...
-1 votes
1 answer
367 views

How long does it take for zinc oxide powder and heinz vinegar to fully react into zinc acetate at a 1:2 ratio of zinc:heinz vinegar? [closed]

How long should I leave a solution of zinc oxide powder and heinz vinegar in order for it to react as completely as possible? The solution is 1(zinc oxide powder):2(heinz vinegar) in a glass flask. ...
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 ...
4 votes
1 answer
116 views

Can heterocyclic molecules form sandwich-like complexes?

As unsaturated heterocycles have the same planar structure as cyclopentadiene ion/benzene "sandwich" compounds, I was wondering if a similar coordination between metals can be achieved. When ...
3 votes
1 answer
27k views

Is there a reaction between ethanol and aluminum?

Is there a potential reaction that would occur between ethanol and aluminum? If so, would it potentially create anything toxic?
4 votes
1 answer
225 views

Do organopolonium compounds exist?

Analogues of alcohols exist for all the heavier Group 16 elements, namely sulfur, selenium, and tellurium. Would polonium also be able to form a "polonol" like $\ce{CH3PoH}$?
3 votes
1 answer
374 views

Can a carbon that has 5 bonds be explained by saying that one of its bonds is a coordination bond?

In my organometallic chemistry class at the university, the doctor told us that compound μ³-CO-[Fe₄(CO)₁₂]²⁻ had the structure that appears in the image. As you can see, there is a pentavalent carbon. ...
-4 votes
1 answer
186 views

Why are tri-organotin chloride compounds so dangerous? [closed]

Organotin compounds are compounds with the tin-carbon bond and some of them(specifically the tri-organo chloride ones) are as toxic as hydrogen cyanide. Why is this though as I don't really know some ...
10 votes
1 answer
427 views

How does cyclopentadienyl anion act as reducing agent?

I am a second year university student, so I'm afraid my chemistry isn't great. I am looking for an explanation of how the $\ce{Cp-}$ anion acts as a reducing agent. To contextualise - in a simple ...
15 votes
2 answers
4k views

Why does magnesium prefer to insert into C–Br bonds over C–Cl bonds?

In the formation of a Grignard reagent from a compound possessing both bromine and chlorine, magnesium preferentially inserts into the C–Br bond over the C–Cl bond. For example, the formation of a ...
0 votes
1 answer
132 views

Redox reaction of cycloheptatriene ligand

The reaction I really don't understand is the second one which produces the cycloheptatriene ring with a positive charge. The only thing I can think of is that the hydrogen is being ejected and ...
2 votes
1 answer
441 views

How to "draw" a coordination bond (dashed bond) in MOLFILE?

How can we "draw" a coordination bond (dashed bond) in MOLFILE? I cannot find a bond property or option that would allow me to choose such a thing. So many drawings of organo-metallic ...

1
2 3 4 5