Home >
Community >
Thermodynamic stability of meta-xylene over ortho- and para-isomers
Upvote
20
Downvote
+ Chemistry
+ Stability
Posted by
Mel B.
Thermodynamic stability of meta-xylene over ortho- and para-isomers
The thermodynamic stability of m-xylene over o-xylene or p-xylene can be deduced by considering the hyperconjugative effect. More specifically, resonance forms with a positive charge on methyl-substituted carbons are more important than resonance forms with a negative charge on them, as the methyl group stabilises the positively charged carbon by hyperconjugation.
In the o- or p- isomers, the hyperconjugation of one methyl group produces negative charge at ortho and para position where another methyl group resides. This is highly destabilising. But, in the m-isomer, hyperconjugation does not destabilise the structure and both methyl groups' hyperconjugation effects act in a cooperative way with each other.
The thermodynamic stability of m-xylene over o-xylene or p-xylene can be deduced by considering the hyperconjugative effect. More specifically, resonance forms with a positive charge on methyl-substituted carbons are more important than resonance forms with a negative charge on them, as the methyl group stabilises the positively charged carbon by hyperconjugation.
In the o- or p- isomers, the hyperconjugation of one methyl group produces negative charge at ortho and para position where another methyl group resides. This is highly destabilising. But, in the m-isomer, hyperconjugation does not destabilise the structure and both methyl groups' hyperconjugation effects act in a cooperative way with each other.
@SoumikDas This may seem very basic, but I find the representation of hyperconjugation in your diagram a little weird. Traditionally, when we make hyperconjugation structures in alkenes, dont we break the C-H bond and shift the π bond one place to get a sort of allylic carbanion with the release of a proton?More
@YusufHasan This is just one step away from breaking the C–H bond; all you need to do would be to detach that H+ from the CH3 group and make a double bond between the CH2 and the adjacent positive charge: $$\ce{H-CH2-C+ <-> H+$\cdots$CH2=C}$$ It doesnt affect the subsequent analysis that the negative charge is delocalised onto C-2 and C-4 of the benzene ring.More
The thermodynamic stability of m-xylene over o-xylene or p-xylene can be deduced by considering the hyperconjugative effect. More specifically, resonance forms with a positive charge on methyl-substituted carbons are more important than resonance forms with a negative charge on them, as the methyl group stabilises the positively charged carbon by hyperconjugation.
In the o- or p- isomers, the hyperconjugation of one methyl group produces negative charge at ortho and para position where another methyl group resides. This is highly destabilising. But, in the m-isomer, hyperconjugation does not destabilise the structure and both methyl groups' hyperconjugation effects act in a cooperative way with each other.
The thermodynamic stability of m-xylene over o-xylene or p-xylene can be deduced by considering the hyperconjugative effect. More specifically, resonance forms with a positive charge on methyl-substituted carbons are more important than resonance forms with a negative charge on them, as the methyl group stabilises the positively charged carbon by hyperconjugation.
In the o- or p- isomers, the hyperconjugation of one methyl group produces negative charge at ortho and para position where another methyl group resides. This is highly destabilising. But, in the m-isomer, hyperconjugation does not destabilise the structure and both methyl groups' hyperconjugation effects act in a cooperative way with each other.
More
VOTE
VOTE
VOTE
VOTE