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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3 votes
0 answers
78 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
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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 ...
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4 votes
1 answer
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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 ...
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-1 votes
1 answer
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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
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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
97 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 ...
2 votes
0 answers
48 views

Why do alkali metals form coordination compounds like transition metals? [duplicate]

I've recently read that there are a type of cyclic ethers called "crown ethers" than can coordiate certain cations like potassium and sodium. How is this possible if they have no d-orbitals (...
3 votes
1 answer
160 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. ...
9 votes
1 answer
276 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 ...
0 votes
1 answer
67 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 ...
1 vote
0 answers
25 views

Zetasizer - How can the Z-average mean be lower than all intensity measurements?

I recently used a Malvern Zetasizer on samples of Au nanoparticles in order to determine the size of the particles (we are looking for significant shifts in particle size between samples, and as such ...
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Why is the synthesis of graphene through alkyne trimerization not viable?

I have been looking for a rationale on this as massive polycyclic aromatic hydrocarbons have been synthesized this way, and with Graphene just being an indefinite expansion of aromatic rings, this has ...
0 votes
0 answers
256 views

Advantage of Ir-based vs Alq3 OLED material, is quantum yield more important over the cost?

This Wikipedia page https://en.wikipedia.org/wiki/OLED#Material_technologies mentions a couple of molecules that are used for OLED. The Ir-based compound has ~ 100% quantum efficiency, while Alq3 may ~...
2 votes
1 answer
158 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 vote
0 answers
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Can molecular systems display negative magnetic susceptibility of a higher magnitude than bismuth?

Bismuth has the biggest value when it comes to a negative magnetic susceptibility than all other elements, ignoring superconductors, as they would have a value of -1. Yet, when tables displaying ...
3 votes
0 answers
174 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 ...
6 votes
1 answer
273 views

Effect of metal identity on CO bond length in carbonyl complexes

In organometallic carbonyl complexes, a back-donation effect occurs: the σ molecular orbital of CO yields electron density to an orbital of the appropriate metal atom, and in turn, a d orbital of ...
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3 votes
2 answers
107 views

Can a Grignard reagent form magnesium halide with an alkyl halide? [duplicate]

$$\ce{RMgX + R'X' -> RR' + MgXX'}$$ Is this reaction possible? I am not able find any reference to it in the books that I have. Anyone has a reference?
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1 vote
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Does concerted oxidative addition follow first-order kinetics?

So my professor for organometallic chemistry described the different mechanisms for oxidative addition and in talking about the concerted mechanism he said that it had first order kinetics. I find ...
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4 votes
1 answer
102 views

Why is the trans-effect of nitrile ion (cyanide) weaker than acetonitrile (methyl cyanide) in octahedral chromium complexes?

I was reading a paper which built a series of trans-philicity (a term they coined to indicate both kinetic trans-effect and thermodynamic trans-influence) from extensive calculations. And I found that ...
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4 votes
0 answers
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What does pentamethylarsenic smell of? [closed]

Trimethylarsine smells of garlic. According to Wikipedia, pentamethylarsenic smells like pentamethylantimony but I can't find the smell of that anywhere. What does pentamethylarsenic smell of?
7 votes
1 answer
479 views

How to interpret the relation between CO stretch frequencies and backbonding strength for polycarbonyl compounds?

I am working on a series of octahedral complexes of the type $\ce{[M(CO)2(CH3)X3]-}$ where $\ce{M} = \ce{Co}, \ce{Rh}, \ce{Ir},$ and $\ce{X}$ is a range of ligands (halide, cyanide, nitrosyl, etc.). ...
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2 votes
1 answer
492 views

Reaction of acyl chloride with excess Grignard reagent

I have a reaction to which I must find the majority organic product. I think I found the correct product but the fact that the reaction takes two moles of propylmagnesiumbromide confuses me a bit. I ...
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3 votes
1 answer
101 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 ...
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-4 votes
1 answer
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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 ...
3 votes
0 answers
124 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 $\...
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4 votes
1 answer
186 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
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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(...
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2 votes
0 answers
26 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 ...
3 votes
0 answers
39 views

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 ...
5 votes
0 answers
46 views

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 ...
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Why does π-backbonding in a metal-carbonyl complex lead to a decrease in C-O bond strength?

I understand that π-backbonding in this complex involves the σ-donation of carbonyl to an empty d orbital of the metal, and the π-donation of the d electrons of the metal to the π* MO of the carbonyl. ...
0 votes
0 answers
113 views

The role of PIDA in C-H activation reactions

PIDA ((Diacetoxyiodo)benzene) is a hypervalent iodine(III) compound that acts an attractive oxidizing agent in most of the transition metal catalyzed reactions. Can someone explain me the mechanism of ...
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5 votes
0 answers
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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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4 votes
0 answers
60 views

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}...
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7 votes
2 answers
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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 ...
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1 vote
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What is the proper use of the term "pi-donor ligand"?

Robert Crabtree's The Organometallic Chemistry of the Transition Metals (7e) describes a pi-donor ligand as being a pi-donor "as a result of the lone pairs that are left after one lone pair has ...
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1 vote
1 answer
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Can copper sulfate react with terpenes (such as limonene and terpinenes) at room temperature?

I am just wondering, can I make a metalorganic or organometallic complex of copper and limonene/terpinene/phellandrene in the form of lime oil? If so, what is the formula of the complex formed? I ...
2 votes
0 answers
61 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 ...
-1 votes
1 answer
77 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?
4 votes
1 answer
2k 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 ...
4 votes
0 answers
103 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 ...
0 votes
1 answer
386 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,...
0 votes
0 answers
67 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)
3 votes
1 answer
226 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?
1 vote
0 answers
527 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: ...
2 votes
0 answers
72 views

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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9 votes
1 answer
270 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 ...
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-2 votes
1 answer
147 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
4 votes
0 answers
52 views

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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