Benzene Stability: Bond Dissociation vs. Aromaticity

In summary, the stability of benzene is not necessarily reflected in its bond dissociation energy or bond length alone. Instead, it is due to the delocalization of pi electrons, which breaks the aromaticity when a bond is broken. To fully understand the stability, a comparison with a similar molecule without aromatic stabilization may be necessary.
  • #1
mayer
38
0
Might be a stupid question but got to ask. The bonds of benzene have a bond dissociation energy in between that of a single C-C bond and an alkene yet its stability is much higher that expected due to aromaticity/e- delocalization. Is stability not necessarily reflected in bond dissociation energy. This fact had slipped my mind till I found out that the IR absorption is lower for a aromatic C-C bond then it is for a Alkene C-C bond.

Thanks
 
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  • #2
Sorry, but I don't get your question.
Do you have some numbers to make your point on dissociation energy clearer?
And what is lower? IR absorption intensity, frequency?
 
  • #3
That's probably because when you break the one and half bond you also break the aromaticity of the benzene ring.
 
  • #4
Ah i probably shouldn't have said bond dissociation. The values I had were bond length values. Alkene ( 1.34 A) and Aromatic C=C (1.38 A). I don't recall the single bond bond length though it was longer than those aforementioned. The point is that the benzene bond lengths were measured longer than that of an alkene. The stability does not seem to be apparent in the bond length when it comes to Benzene. That is my question, hopefully that clears things up. My apologies for the confusion.
 
  • #5
In benzene, you would expect the bond length to be between that of a single and a double bond, which is what you observe. I don't see how you could deduce further stabilization from the bond length alone.
 
  • #6
Well bond length is a partial indicator of molecular stability because shorter bonds equal stronger bonds equals less reactive. My question is where is the stability represented within the molecule if not in the bonds.
 
  • #7
I'm not sure if it's a good way to simply determine the stability by bond length but a part of the stability of benzene comes from the sort of delocalized pi electrons. I don't know the role of bond length plays here; the stability of benzene might be due to the fact that once you break one bond you break the aromaticity like I mentioned.
 
  • #8
mayer said:
Well bond length is a partial indicator of molecular stability because shorter bonds equal stronger bonds equals less reactive. My question is where is the stability represented within the molecule if not in the bonds.

It probably is, but to see it, you would have to compare the bond length in benzene with that in another molecule having similar structure and bond order but no aromatic stabilization. Anti-aromatic molecules come to mind, but these show usually bond length alternation or deformation.
However, this comparison may be a fun project using some ab initio quantum chemistry program where geometry optimization can easily be constrained to allow only for equal bond length and planar molecules .
 

1. Is benzene more stable due to bond dissociation or aromaticity?

Benzene is more stable due to its aromaticity, which is a result of its delocalized π electrons. This delocalization spreads out the electron density and makes the molecule more stable compared to a hypothetical molecule with isolated double bonds.

2. How does bond dissociation energy affect the stability of benzene?

The bond dissociation energy of benzene is higher than that of a normal alkene, indicating that the C-C bonds in benzene are stronger. This contributes to the stability of benzene, as it requires more energy to break the bonds and disrupt the delocalization of the π electrons.

3. Why is benzene considered to be a highly stable molecule?

Benzene is highly stable due to its aromaticity, which makes it resistant to chemical reactions that would normally break apart other molecules. The delocalized π electrons also contribute to its stability, as they help distribute the charge and prevent any one bond from becoming too weak.

4. How does the structure of benzene contribute to its stability?

The structure of benzene, with its alternating single and double bonds, allows for the delocalization of π electrons. This creates a more stable electron cloud, reducing the energy required for chemical reactions to occur. Additionally, the hexagonal shape of benzene also contributes to its stability, as it allows for efficient overlap of orbitals.

5. Can benzene's stability be affected by external factors?

Yes, benzene's stability can be affected by external factors such as temperature, pressure, and the presence of other molecules. For example, increasing the temperature can cause the delocalized π electrons to become more mobile, making benzene more reactive. Additionally, the presence of other molecules can interact with the π electrons and alter the stability of benzene.

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