What Factors Influence the Basicity Order of Substituted Anilines?

[sachin123]

Hey folks.
The orders given are stated in my book.I'm here to ask why.

basicity: p-methyl aniline>m-()>aniline>o-()
p exerts hyperconjugation and +I,m only +I ,but ortho exerts hyperconjugation and higher +I.
Shouldn't o-methyl aniline have high basicity?

basicity: aniline>m-nitro()>p-nitro()>o-nitro()
Why is o- at last?Shouldn't it move NH2 out of plane so that no -R takes place?

And is the ortho effect applicable to all substituents?Can you clear this for me?
Thank You.

 

[sachin123]

PLease tell me if my post isn't clear(and where).

 

[Phrak]

Ask the moderators of this forum to move your thread to the Chem folder. Send a PM to Moonbear.

 

[sachin123]

This is the chem place isn't it?