Pyridine vs Benzene stability

[andyjl]

pyridine is more stable than benzene according to kaplan, but doesn't explain why. Does it have something to do with pyridine's heterocyclic atom, N, having a free lone electron pair? Someone please explain.

Thanks in advance.

---

Members don't see this ad.

 

[AaBbZz]

I think it has something to do with the fact that pyridine is a cyclohexane and can bend and twist to form a stable molecule. Benzene is planar and can not twist or bend to add more stability to the molecule.

I know this is the reason why cyclohexane is more stable then benzene so i am assuming this reasoning would work for pyridine, not 100% positive though

 

[alltheway]

First things first, they are both aromatic so that can't be the reason why pyridine is more stable than benzene. However the lone pairs on the Nitrogen do not contribute to the cyclic system since they are orthogonal therefore when it is protonated (having a plus charge on the nitrogen), its lone pair of electrons with another hydrogen would not disrupt the system making it still stable whereas a benzene ring when one of its bonds is broken the plus charge on it ruins the aromaticity which makes it less stable.
I hope this is clear enough to understand. This is the way that I understood why pyridine is more stable than a benzene ring. If you have trouble understanding this just send me a private message then.

 

[Danny289]

pyridine is more stable than benzene according to kaplan, but doesn't explain why. Does it have something to do with pyridine's heterocyclic atom, N, having a free lone electron pair? Someone please explain.

Thanks in advance.

'I am not sure about my answer, but I think in pyridine we have "N" atom then is more electronegative than "c" result we will have N-C bond that is stronger bond than C-C

 

[Saber tooth]

First things first, they are both aromatic so that can't be the reason why pyridine is more stable than benzene. However the lone pairs on the Nitrogen do not contribute to the cyclic system since they are orthogonal therefore when it is protonated (having a plus charge on the nitrogen), its lone pair of electrons with another hydrogen would not disrupt the system making it still stable whereas a benzene ring when one of its bonds is broken the plus charge on it ruins the aromaticity which makes it less stable.
I hope this is clear enough to understand. This is the way that I understood why pyridine is more stable than a benzene ring. If you have trouble understanding this just send me a private message then.

I agree, since N in pyridine has lone pairs of electrons which are ortagnal and pyridine donates electrons, its aromaticity is not distroied making it more stable then benzen, which has no free electrons.