[eglaud]

Viewing the molecule on the link below, which nitrogen would be more likely to accept a proton?  If you have the slightest idea please share, I have a test tomorrow and any idea can give me the understanding needed to figure out the rest. Thanks!

http://www.chemspider.com/Chemical-Structure.773.html?rid=039b7897-d8ef-4f06-b3b0-de77ce6f844d

[eglaud]

p.s. looking at a pka calculator I am pretty sure the answer is the right one is more likely to accept a proton, but again, not sure why. I understand hybridization and resonance, but I am not sure how to relate this.

[eglaud]

Well I've cracked the code, resonance was our friend all along. I protonized both sides, the difference was the left side was stuck with that nasty cation, while when the right side had the hydrogen added it could rely on resonance to balance the charge out, so to speak

[mjc123]

Compare the pKas of pyridine-H⁺ (5.0) and pyrrole-H⁺ (0.5). What does that tell you?

[orgopete]

Hint, this is a question about aromaticity. Which protonation of imidazole will maintain aromaticity?