text: The lone pair of electrons on the nitrogen atom is delocalized into the carbonyl group, thus forming a partial double bond between nitrogen and carbon. In fact the O, C and N atoms have molecular orbitals occupied by delocalized electrons, forming a conjugated system. Consequently, the three bonds of the nitrogen in amides is not pyramidal (as in the amines) but planar. This planar restriction prevents rotations about the N linkage and thus has important consequences for the mechanical properties of bulk material of such molecules, and also for the configurational properties of macromolecules built by such bonds. The inability to rotate distinguishes amide groups from ester groups which allow rotation and thus create more flexible bulk material.
  The C-C(O)NR core of amides is planar.  The C=O distance is shorter than the C-N distance by almost 10%.  The structure of an amide can be described also as a resonance between two alternative structures: neutral (A) and zwitterionic (B).
  It is estimated that for acetamide, structure A makes a 62% contribution to the structure, while structure B makes a 28% contribution (these figures do not sum to 100% because there are additional less-important resonance forms that are not depicted above). There is also a hydrogen bond present between the hydrogen and nitrogen atoms in the active groups. Resonance is largely prevented in the very strained quinuclidone.
  In their IR spectra, amides exhibit a moderately intense ν band near 1650 cm.  The energy of this band is about 60 cm lower than for the ν of esters and ketones.  This difference reflects the contribution of the zwitterionic resonance structure.