Metal Organics

[YT2095]

I`ll post this here anyway even though most of our chemists are gone,

 

Take Phenol or Benzene for example, they can have all sorts of attatchemnts to them, NO2 (O2N), R, OHs, Halides, Amines etc...

even Sodium.

How about Other metals such as Copper or Chromium, Manganesse etc...

 

now I know it can be done with the Acids of these, Benzoic, Phenolic etc..

is there a way to attatch them without them being Acids?

 

OR

 

Use the acid part to get them on there, and then strip that part leaving the metal ions in place?

[woelen]

There are two classes of metallic organics. One class is nothing special and can be regarded as salts of organic ions. Examples of this are plentyful, e.g. sodium acetate, calcium citrate, magnesium lactate, copper benzoate, etc. The metal is not really bonded, it is present in conjunction with a negative ion.

 

A little bit closer to a real organic metal compound are the more or less covalently bonded compounds, like "ferric oxalate", basic beryllium acetate, copper citrate. These are complexes of common anions and metal ions. The bond is not purely ionic anymore. Still, this is not specific to metal organics. This also exists in the inorganic domain.

 

Real metal organics are those, where the metal is directly bonded to a carbon atom. A well known example are the Grignard reagents, where Mg is bonded to an aliphatic carbon atom. These compounds also exist for other metals, most notably transition metals. This kind of compounds can be quite stable, but they usually are EXTREMELY air-sensitive, either due to humidity in the air, due to oxygen in the air, or both. This is an area of research, where very unusual compounds are found and the research of these compounds also gives new insights in properties of metals. Unfortunately, experimenting with these organometal compounds is beyond the reach of the hobby-chemist. These are very hard to make and require specialized air-free equipment. The first real organometallic compound, which was recognized as such probably was nickel carbonyl, Ni(CO)4, but it might be that there are even earlier other examples, but I'm not aware of these.

[YT2095]

it`s interesting to note that Zinc, copper, molybdenum, manganesse, even chromium etc... are all essential trace elements in plant growth, so there looks to be quite a few bonds made to organics, even Cobalt is used for vitamin B.

 

Nickel Carbonyl is indeed an interesting chem and quite simple, is there something simple but with a "bit more meat" on it as a molecule that could be made?

something like Copper Ethoxide?

[Cesium]

A variety of metal alkoxides exist. See http://www.rareearthproducts.com/catalog/metal_alkoxides_513228_products.htm for example.

[woelen]

A variety of metal alkoxides exist. See http://www.rareearthproducts.com/catalog/metal_alkoxides_513228_products.htm[/url'] for example.

Do these really fall in the class of organometal compounds? I regard them merely as salts of the -O-R group, (e.g. -O-CH2-CH3) for ethoxide. The sodium salt can be made by adding sodium to an alcohol and the other metal alkoxides can be derived from that. These ethoxides do not contain direct metal-C bonds.

[Cesium]

Yes, woelen, they are merely salts, nothing like a Grignard or organolithium compound, but I was responding to YT's query about copper ethoxide.

[raptor]

I'm sure dimethylmercury ([ce] H3C\sbond Hg\sbond CH3[/ce]) contains C - metal bonds.

 

(It's also a truly horrible poison, see: http://www.chm.bris.ac.uk/motm/dimethylmercury/dmmh.htm)

[YT2095]

fascinating! and nice link too

and yes, there is a clear bond in that stick diag indicating the C-Hg bond and then the OH group.

 

just out of curiosity DMSO seems to do a similar thing with almost everything, would DMSO be considered an Organic material?

[bob000555]

Wouldn’t calcium carbide be considered a metal organic also?

edit: aparently not: http://en.wikipedia.org/wiki/Category:Organometallic_compounds

Ferrocene sounds interesting.

[Cesium]

Binary cyanides, thiocyanides, carbides, and compounds with similar anions are usually classified as inorganic compounds even though they contain carbon. Semantics, I guess. And even so they would not meet our definition of "metal organic" because they are just salts.

 

Ferrocene is a great example though.

[jdurg]

Hemoglobin is a pretty good organometallic compound. I think we've been making that one for millenia.

[bob000555]

Chlorophyll from plants would be one also.

[Invader_Gir]

Since Grignard reagents are metal organics, I figured this would be appropriate place to ask: Will Grignard reagents react with ethers? I know that they do with epoxides, but that reaction is favorable because of ring strain, but just your typical R-O-R' ethers.

 

Thanks!

[Bluenoise]

Since Grignard reagents are metal organics, I figured this would be appropriate place to ask: Will Grignard reagents react with ethers? I know that they do with epoxides, but that reaction is favorable because of ring strain, but just your typical R-O-R' ethers.

 

Thanks!

 

Well no they don't.

Remember ethers are the common solvent used in a grignards reaction.

[Invader_Gir]

Oh yeah, *blush* forgot about that. Thanks!

[budullewraagh]

It should be noted that Grignards can be made by addition of magnesium to alkyl halides and that organolithium reagents can be made by addition of n-butyl Lii, sec-butyl Li and tert-butyl Li, though the latter is most applicable and most dangerous.

 

Also, trimethylaluminum is commonly used as a catalyst for such reactions as the Weinreb amidation of esters.

 

Also, organocuprates (Gilman reagents) are often used to favor 1,4 addition over 1,2 addition to a,b-unsaturated carbonyls and are generated in situ by reaction of the corresponding organolithium with CuI to form R2CuLi.