[metallica00789]

Hi,
The C13 NMR for acetanilide

Shows carbons 5 to be less deshielded compared to carbon 4. This does not make sense to me since carbons 5 are closer to the electrognegative nitrogen, so they should be more deshielded. What do you guys think?

[Babcock_Hall]

Draw a resonance form involving the unshared pair of electrons on nitrogen.

[metallica00789]

I tried to draw the resonance for the compound, and I noticed high electron density at the ortho and para positions, but I am thinking that since the ortho position is closer to the electron negative nitrogen atom, it should be more deshielded compared to the para position.

[Babcock_Hall]

Now I think I understand you question a little better, but I don't have a good answer yet.  I'll look at it again this evening.