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Homework Help: Do Amine Orbitals Change Shape

  1. Nov 30, 2012 #1
    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

    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?
  2. jcsd
  3. Dec 1, 2012 #2


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    Gold Member

    There is likely a shape change due to the electron donating groups but you should understand that the orbital in question is not a p orbital. It is an SP3 orbital. Also, it is generally not very helpful to focus on the size of the orbital in alkyl amines as other effects like steric and solvation usually dominate the basicity of alkyl amines.
  4. Dec 1, 2012 #3
    Thank you for clearing this up for me.
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