# Which one is the strongest base among the following compounds?

I am confused between option (2) and (4). Both lone pairs of nitrogen are localized, so next, I looked at the hybridization of $$\ce{N}$$ in each compound. As in (2), the $$\ce{N}$$ is $$\mathrm{sp^2}$$ hybridized and therefore is more electronegative, I assumed it would be a weaker base compared to (4).

But the answer is (2). I drew the protonated structures and found that there is resonance in the compound (2).

I was taught that electronegativity is more important in questions like this. Is this a wrong concept? Any help is appreciated!

• chemistry.stackexchange.com/questions/96513/… Jan 7 '20 at 18:11
• You are comparing nitrogen with nitrogen; how can electronegativity be an issue? Jan 7 '20 at 18:32
• This is also closely related to: chemistry.stackexchange.com/q/125449/61578. That link has an answer why guanidine is stronger base. Jan 7 '20 at 19:04
• No that is a myth propagated by some organic chemists. Electronegativity is a property of an element, nothing more, nothing less. Hybridisation is also just a mathematical concept, it doesn't change what the atom or molecule is. Jan 7 '20 at 23:58
• @RahulVerma M.S. Chouhan elementary problems in organic chemistry for JEE. I'm using this for NEET but if you're preparing for JEE, my teachers recommend using the advanced version. Jan 17 '20 at 15:43