I came across the following two details about m-xylene:
m-Xylene is thermodynamically most stable compound among o-xylene, m-xylene, and p-xylene.
m-Xylene is most reactive towards nitration and sulphonation among the others.
I did some research and was able to find valid reasons for both the statements, but they still seem to be contradicting each other. How can m-xylene be most stable as well as most reactive at the same time?
Could someone please clarify my doubt and also, add more specific details if required.
"In m-xylene, the two methyl groups reinforce one another in their activation of the ring, while in o- and p-xylenes the methyl groups cancel the ring activation to some extent."
I totally agree with this statement and it clearly explains the reason behind the the reactivity of m-xylene towards nitration and other such reactions.
But I realized that I was considering this statement as the reason behind the stability of m-xylene as well. Reference: Thermodynamic stability of meta-xylene over ortho- and para-isomers
The reasoning seems to be fitting for both the cases (I do realize now that stability and reactivity are not opposing terms necessarily).
So, is the reason why m-xylene is most thermodynamically stable the same reason why m-xylene is most reactive towards nitration? Could someone please confirm this or add their inputs if I am making some mistake in correlating terms or in my reasoning.