Question
Rotation is limited around the peptide bond because r____.
Answer
Rotation is limited around the peptide bond because resonance gives the C-N bond partial double-bond character.
Note ↑: The carbonyl carbon of an amide is sp2
hybridized and has trigonal planar geometry. A second
resonance structure can be drawn that delocalizes the nonbonded electron pair on the N atom.
Amides are more resonance stabilized than other acyl compounds, so the resonance structure
having the C=N makes a significant contribution to the hybrid.
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