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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0answers
26 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 ...
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41 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 ...
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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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2answers
54 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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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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1answer
48 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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74 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?
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132 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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1answer
80 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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1answer
88 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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1answer
56 views

Why are tri-organotin compounds so toxic? [closed]

Organotin compounds (organostannane chemistry) are compounds with the tin-carbon bond and some of them(specifically the tri-organo ones) are as toxic as cyanide. Why is this though as I don't really ...
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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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1answer
100 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 $\ce{CH3PoH}$?
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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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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 ...
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37 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 ...
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33 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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24 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. ...
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32 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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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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29 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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259 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 ...
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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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1answer
134 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 ...
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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 ...
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1answer
56 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?
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1answer
695 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 ...
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70 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 ...
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1answer
140 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,...
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62 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)
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1answer
142 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?
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296 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: ...
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63 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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214 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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1answer
45 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
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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 ...
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1answer
169 views

Reason for double acylation of ferrocene only occurring with certain reagent combinations

Can anyone explain why the acylation of ferrocene produces the following results: Ferrocene + acetic anhydride + AlCl3 ==> mono-acylated ferrocene but: Ferrocene + acetyl chloride + AlCl3 ==> di-...
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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 ...
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91 views

Organometallic and oxygen

I often read that reactive organometallics must be handled under an inert atmosphere because they react with oxygen in the atmosphere. This applies to grignard reagents, organolithium reagents, and ...
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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 ...
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1answer
149 views

What is the mechanism of this reaction?

I've been stuck with this for some time. I just don't see it. As the reactant is Pd(0), I think oxidative addition will happen to the bromine. Then I would say an insertion reaction happens. However ...
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283 views

Triphenylphosphine (PPh3) vs. 1,2-bis(diphenylphosphino)ethane (dppe) ligand?

What about $\ce{NiCl2(dppe)}$ makes it a more efficient catalyst for Suzuki cross-coupling as opposed to $\ce{NiCl2(PPh3)2}$ or $\ce{NiCl2(PCy3)2}$? How does the dppe ligand increase the reactivity of ...
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1answer
596 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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1answer
344 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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268 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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41 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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94 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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46 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
164 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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51 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 ...