1. The problem statement, all variables and given/known data Does the size of the p orbital with the lone pair change when adding electron donating groups, such as methyl? 2. Relevant equations N/A 3. The attempt at a solution I know the electron availability increases on the nitrogen's lone pair, making it a better base, but I'm wondering if the orbital shape changes. I think the p orbital would increase in size with an electron donating group. Should I be thinking of orbitals in a static sense (unchanging shape) with a particular atom or do the orbitals' shape change depending on the electron withdrawing/donating group? Let's say I want to attach more methyl groups to the amine, does the nitrogen orbital with the lone pair get even bigger?