Questions tagged [organometallic-compounds]
For questions relating to organic compounds which contain a bond between a carbon atom and a metal.
215
questions
1
vote
0
answers
33
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 ...
- 11
0
votes
0
answers
65
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 ...
- 9
0
votes
0
answers
19
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 ...
- 101
-1
votes
1
answer
77
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
666
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
165
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 ...
- 1
1
vote
0
answers
82
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 ...
4
votes
1
answer
226
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?
- 59
0
votes
1
answer
84
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 ...
3
votes
0
answers
152
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
104
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 ...
- 51
4
votes
1
answer
126
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 ...
- 993
-1
votes
1
answer
237
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. ...
- 27
2
votes
0
answers
51
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 ...
- 27
4
votes
1
answer
114
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 ...
- 226
3
votes
1
answer
302
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.
...
10
votes
1
answer
369
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 ...
- 109
0
votes
1
answer
96
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
37
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 ...
- 111
0
votes
0
answers
35
views
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 ...
- 699
0
votes
0
answers
263
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 ~...
- 11
2
votes
1
answer
357
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 ...
- 381
1
vote
0
answers
39
views
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 ...
- 699
3
votes
0
answers
269
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 ...
- 111
7
votes
1
answer
403
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 ...
- 607
3
votes
2
answers
148
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?
- 39
1
vote
0
answers
32
views
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 ...
- 131
5
votes
1
answer
159
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 ...
- 5,637
4
votes
0
answers
83
views
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?
- 165
8
votes
1
answer
1k
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.). ...
- 5,637
2
votes
1
answer
879
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 ...
- 31
3
votes
1
answer
106
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 ...
- 39
-4
votes
1
answer
154
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 ...
- 911
3
votes
0
answers
185
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 $\...
- 5,637
4
votes
1
answer
214
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 $\ce{CH3PoH}$?
- 911
3
votes
0
answers
56
views
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(...
- 131
2
votes
0
answers
29
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 ...
- 147
3
votes
0
answers
50
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 ...
- 147
5
votes
0
answers
56
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 ...
- 123
0
votes
0
answers
138
views
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
137
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 ...
- 51
5
votes
0
answers
33
views
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 ...
- 51
4
votes
0
answers
82
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}...
- 400
7
votes
2
answers
2k
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 ...
- 71
1
vote
0
answers
123
views
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 ...
- 1,905
1
vote
1
answer
302
views
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 ...
user102173
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 ...
- 29
-1
votes
1
answer
96
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?
- 31
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 ...
- 6,218
4
votes
0
answers
125
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 ...
- 898