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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Organic Chemistry synthesis catalyst and conditions: dehydration and cyclication

I have been thinking new ways to synthesis. There are two routes. 1)dehydrating an amino 5 member heterocycle to make pyridine derivaties but what suitable catalyst? This method is straightforward but ...
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134 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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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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2answers
6k 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,...
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1answer
49 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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91 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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2answers
12k views

Why can't the reaction of grignard reagent with carboxylic acid give a ketone?

I understand that a Grignard reagent can act both as a base and a nucleophile. It acts as a base in the presence of a proton source (eg: alcohols, amine, water, etc). But when reacting with a ketone ...
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50 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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Bonding between rings and iron atom in ferrocene

How are the 10 vertical bonds in Ferrocene (sandwich structure) connected, by what type of bonds? What is the real structure of ferrocene? Concerning the 10 vertical extra long bonds?
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1answer
58 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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1answer
175 views

Mechanism of a gold catalyzed addition to triple bond

I needed to draw the reaction mechanism for this reaction: So, after consulting some literature I drew this mechanism: But, I am not sure about the last step. Does the $\ce{H+}$ just substitute the $...
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55 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
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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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45 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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1answer
182 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
25 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 ...
3
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1answer
110 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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1answer
68 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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31 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 ...
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1answer
43 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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1answer
6k 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 ...
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1answer
2k views

Coordination number of carbon in methyllithium tetramer

According to J. D. Lee's Concise Inorganic Chemistry, the coordination number of carbon in $\ce{Li4(CH3)4}$ is $7$. But the structure of the tetramer is Doesn't carbon have coordination number $6$ ...
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1k views

Inorganic chemistry reaction mechanisms

Are there well developed reaction mechanisms in inorganic chemistry like those in organic chemistry? If yes, please suggest an easy to follow reference.
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1answer
23k views

Reduction of alkyl halides to alkanes

For all the three parts, only methane has been given as the product in my textbook. In 1) and 2), according to the mechanism I wrote, I get both ethane and methane as products. I think both these ...
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64 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 ...
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1answer
150 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
337 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
269 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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122 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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36 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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75 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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1answer
92 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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43 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
300 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 ...
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42 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 ...
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1answer
82 views

Why has nature evolved to put a porphyrin (i.e. chlorophyll) as the chromophore in a leaf? [closed]

I'm stumped by this question: Why has nature evolved to put a porphyrin (i.e. chlorophyll) as the chromophore in a leaf? I've thought that it might have something to do with how sun emits light ...
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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 ...
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1answer
823 views

Why do aromatic compounds have an upfield shift upon coordination to metals?

Why do aromatic compounds have an upfield shift upon coordination to metals e.g. ferrocene? The 1H NMR shows a single environment at ~4.1 ppm. This is in contrast to the usual aromatic shift of ...
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60 views

Why doesn't Grignard reagent attack alkyl halides [duplicate]

When we add magnesium to alkyl halide, Grignard reagent is formed. $$\ce{R-X + Mg -> RMgX } $$ It is highly nucleophilic in nature. Now at this time the electrophilic alkyl halide is also present ...
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1answer
326 views

How does 1-bromo-2-fluorobenzene react with lithium amalgam? [closed]

How does this organometallic reagent react with 1-bromo-2-fluorobenzene? Does it react like Grignard reagent? If the product of this reaction is then reacted with furan, what will be the final product?...
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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 ...
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1answer
722 views

Will ferrocene undergo electrophilic aromatic substitution?

Ferrocene has two structure 1 and 2.It is bonded to an aromatic ion cyclopentadienyl anion.Aromatic species such as benzene , cyclopentadienyl anion undergo electrophilic aromtic substitutions. Then,...
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142 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 ...
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Alkyl insertion with cobalt and CO

Reaction of $\ce{(Cp)Co(Me)2(CO)}$ in the presence of excess $\ce{CO}$ yields two different organic products, $\ce{A}$ and $\ce{B}.$ The only metal-containing product is $\ce{(Cp)Co(CO)2}.$ The IR ...
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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 $\alpha,\beta$-...
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20 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 ...
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42 views

Electron-donating trends for ligands bound to metal complexes

Imagine an inorganic complex with a bunch of terminal ligands. All else the same, would $\ce{F-}$ or $\ce{Br-}$ ligands be more electron-donating and why? Of course, in terms of $\mathrm{p}K_{\mathrm{...
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4answers
6k views

Why do Organolithium or Grignard reagents act as nucleophiles and not as bases with aldehydes and ketones

I've read entire Chapter 14: Organometallic Compounds of Francis Carey's "Organic Chemistry" but I still didn't get an answer to my question. Quote from the book: Because of their basicity ...
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1answer
143 views

What's wrong with using tin in medicinal chemistry?

I just read this In the Pipeline post and I was slightly confused by a statement on the use of tin. Lowe reports on this paper, which describes a synthetic route to spiro heterocycles using tin ...