What causes absence of mesomeric interaction in benzoic acids?

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In summary, the mesomeric effect in acids refers to the influence of substituents on the distribution of electron density in a molecule. This effect can either increase or decrease the acidity of an acid, depending on the nature of the substituent. It is related to but not identical to resonance. The mesomeric effect can also affect the stability of acids by delocalizing the negative charge in the molecule. It can also be used to predict the reactivity of acids, but other factors should also be considered.
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Vectorcrust
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Why there is no mesomeric interaction between [itex]\pi[/itex]-electrons of aromatic ring and [itex]\pi[/itex]-electrons of carbonyl group in benzoic acids?
 
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  • #2
I would think it was because the postive charge was bourne fully by the dissociated proton rather than the carbonyl carbon attached to the aromatic ring.
 
  • #3
There are no valid resonance structures satisfying the octet rule.
 

Related to What causes absence of mesomeric interaction in benzoic acids?

1. What is the mesomeric effect in acids?

The mesomeric effect in acids is a phenomenon in which the distribution of electron density in a molecule is affected by the presence of a substituent. This can lead to differences in the acidity or basicity of the molecule.

2. How does the mesomeric effect influence the acidity of acids?

The mesomeric effect can either increase or decrease the acidity of an acid, depending on the nature of the substituent. Electron-withdrawing substituents, such as a nitro group, can increase the acidity by pulling electron density away from the acid group. On the other hand, electron-donating substituents, such as an alkyl group, can decrease the acidity by donating electron density to the acid group.

3. Is the mesomeric effect the same as resonance?

No, the mesomeric effect and resonance are related but not identical concepts. Resonance refers to the delocalization of electrons in a molecule, while the mesomeric effect specifically refers to the influence of substituents on this delocalization.

4. How does the mesomeric effect affect the stability of acids?

The mesomeric effect can increase the stability of acids by delocalizing the negative charge in the molecule. This is particularly important in carboxylic acids, where the conjugate base is stabilized by resonance. However, in some cases, the mesomeric effect can also decrease stability by destabilizing the conjugate base through the introduction of additional charges.

5. Can the mesomeric effect be used to predict the reactivity of acids?

Yes, the mesomeric effect can be a useful tool in predicting the reactivity of acids. For example, an acid with electron-withdrawing substituents is likely to be more reactive than one with electron-donating substituents, as the former will be more acidic. However, other factors such as steric hindrance and inductive effects should also be taken into consideration when predicting reactivity.

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