Is this compound actually possible?

[RyanJ]

Is it possible for this compound to exist? If so what would its name be?

 

I don't know, looks like it should be - it is substitution to the benzene ring but its been bugging the hell out of me for a few days since the chemistry exam...

 

Just another curiosity

 

-- Ryan Jones

[insane_alien]

I think it would be possible as an oxygen cvering 2 of the carbons is possible.

trimetaoxybenzene maybe?

[RyanJ]

I think it would be possible as an oxygen cvering 2 of the carbons is possible.

trimetaoxybenzene maybe?

 

I'd think it was possible, its not really affecting the delocalised pi electron system so it should be stable... oxygen has its two bonds... Just can't find a reference to it so question if it is actually possible.

 

http://chemicalland21.com/lifescience/phar/1,3,5-TRIMETHOXYBENZENE.htm

 

Is the closest I have found.

 

-- Ryan Jones

[woelen]

There are many reasons why a certain compound cannot exist. Although indeed that compound C6O3 has a valid benzene aromatic ring and the oxygens have two bonds, it probably cannot exist for steric reasons. How do you imagine this molecule to look like in reality? Where would the O-atoms fit in the molecule? The structure you have drawn seems to me one with extremely long bonds between the O-atoms and C-atoms and I expect a very high strain in this molecule.

 

So, in general, a molecule can satisfy all bonding rules, but if it cannot be realized sterically, then still it cannot exist. E.g. CI4 (tetra iodo methane) does exist, but it is quite unstable, because the molecule is really crowded with the big iodines around that small C. The compound C2I6 (hexa iodo ethane) does not exist, it would have such extreme bond strains that simply one of the iodine atoms snaps off the molecule and the molecule breaks apart.

 

Think of the bonds as mechanical springs. A spring does not like to be pressed, nor to be stretched. When it is pressed into a shorted length, then it pushes back, if it is stretched, then it pulls back. If it is pressed too much, or stretched too much, then it breaks into parts and is destroyed. This is exactly what happens with the bonds. These also have a preferred length and shorter or longer bonds (or strongly bent bonds) feel strain. When the strain is too large, it breaks apart, just as the mechanical spring.

[RyanJ]

I think I understand, so even though the structure is valid it probably can't exist because the strain on the long C-O bonds would probably be too much for them to handle making the compound inherantly unstable? Interesting...

 

Tell me Woelen, do you happen to know what its name would be? I think I'd like to do more research into it... I don't know why but I just like the way that molecule looks

 

-- Ryan Jones

[woelen]

The name of that compound, I really don't know. Maybe phenyl-trioxide? But that is not really correct, because phenyl is a C6H5- group, and here we have a benzene-ring with all the hydrogens removed.

 

A better name probably would be trioxo-benzene, analogous to something like trichlorobenzene. With trichlorobenzene you have to say where the chlorines are on the ring, hence you get something like 1,2,3-trichlorobenzene, or 1,2,4 trichlorobenzene (these are two possible isomers, there are more, however). With the oxo-compound, there is only one, so no need to use prefixes, telling where the oxygens are.

 

But, to be honest, I'm not sure about these names. Maybe an organic chemistry specialist can tell more about this.

[RyanJ]

Thanks for the help Woelen Looks like I'll need to do a bit more research about it then!

 

-- Ryan Jones