Home > Community > Is the ammonium substituent (-NH3+) really meta-directing in electrophilic substitution?
Upvote

22

Downvote
+ Amines
+ Regioselectivity
+ Biochemistry
Posted by
Mubarak Abdullahi Khaleed

Is the ammonium substituent (-NH3+) really meta-directing in electrophilic substitution?

If we make a resonance structure for the anilinium ion, with positive charge at either the ortho or the para position, we get a pentavalent nitrogen, which is not possible. So, how is the $\ce{-NH3+}$ group meta-directing in electrophilic aromatic substitution reactions, e.g. in nitration of aniline under acidic conditions?

TOP